[ [], { "name": "5-[1-((3-Amino-4-methyl-5-(phenyldiazenyl)thiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazol (6a)", "yield": 67, "molecularFormula": "C16H18N8S2", "appearance": "Red solid", "mp": { "low": 192, "high": 194, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": 3406, "assignment": "2NH2" }, { "wavenumber": 3298, "assignment": "2NH2" }, { "wavenumber": 3121, "assignment": "2NH2" }, { "wavenumber": 1639, "assignment": "C=N" }, { "wavenumber": 1552, "assignment": "N=N" } ] }, "mass": { "peaks": [ { "mass": 387, "intensity": 6, "assignment": "M+ + 1" }, { "mass": 387, "intensity": 8, "assignment": "M+" }, { "mass": 163, "intensity": 18 }, { "mass": 110, "intensity": 67 }, { "mass": 77, "intensity": 100 } ] }, "hrms": { "found": 386.5 }, "bp": { "units": null }, "nmr1H": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "deltaFrom": 2.42, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 2.52, "multiplicity": "s", "integration": null, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 2.85, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 3.43, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 7.15, "multiplicity": "s", "integration": null, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 7.31, "deltaTo": 7.73, "multiplicity": "m", "integration": 5, "assignment": "Ar-H" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "delta": 16.21, "assignment": "CH3" }, { "delta": 17.1, "assignment": "CH3" }, { "delta": 19.89, "assignment": "CH3" }, { "delta": 114.67, "assignment": null }, { "delta": 120.32, "assignment": null }, { "delta": 121.56, "assignment": null }, { "delta": 128.61, "assignment": null }, { "delta": 139.54, "assignment": null }, { "delta": 143.14, "assignment": "Ar-C" }, { "delta": 154.15, "assignment": null }, { "delta": 161.67, "assignment": null }, { "delta": 167.45, "assignment": null }, { "delta": 169.78, "assignment": null }, { "delta": 176.75, "assignment": "C=N" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "5-[1-((3-Amino-4-methyl-5-(phenyldiazenyl)thiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazol (6a). Red solid (67%); mp 192–194 °C; IR (KBr): ν 3406, 3298, 3121 (2NH2), 1639 (C=N), 1552 (N=N) cm−1; 1H-NMR (DMSO-d6): δ 2.42 (s, 3H, CH3), 2.52 (s, br., 2H, D2O-exchangeable, NH2), 2.85 (s, 3H, CH3), 3.43 (s, 3H, CH3), 7.15(s, br., 2H, D2O-exchangeable, NH2), 7.31–7.73 (m, 5H, Ar-H); 13C-NMR (DMSO-d6): δ 16.21 (CH3), 17.10 (CH3), 19.89 (CH3), 114.67, 120.32, 121.56, 128.61, 139.54, 143.14 (Ar-C), 154.15, 161.67, 167.45, 169.78, 176.75 (C=N); MS m/z (%): 387 (M+ + 1, 6), 387 (M+, 8), 163 (18), 110 (67), 77 (100). Anal. Calcd. for C16H18N8S2 (386.50): C, 49.72; H, 4.69; N, 28.99. Found C, 49.65; H, 4.60; N, 28.78%.", "doi": "10.3390/molecules21010003" } }, { "name": "5-[1-((3-Amino-4-methyl-5-(4-methylphenyldiazenyl)thiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazol (6b)", "molecularFormula": "C17H20N8S2", "yield": 68, "appearance": "Red solid", "mp": { "low": 216, "high": 218, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": 3407, "assignment": "2NH2" }, { "wavenumber": 3317, "assignment": "2NH2" }, { "wavenumber": 3113, "assignment": "2NH2" }, { "wavenumber": 1636, "assignment": "C=N" }, { "wavenumber": 1556, "assignment": "N=N" } ] }, "mass": { "peaks": [ { "mass": 402, "intensity": 11 }, { "mass": 401, "intensity": 18 }, { "mass": 400, "intensity": 29 }, { "mass": 233, "intensity": 19 }, { "mass": 153, "intensity": 69 }, { "mass": 105, "intensity": 100 } ] }, "hrms": { "expected": 400.52, "found": 400.37 }, "nmr1H": { "solvent": "DMSO-d6", "frequency": 300, "peaks": [ { "deltaFrom": 2.23, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 2.42, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 2.5, "multiplicity": "s, br.", "integration": 2, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 2.84, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 3.47, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 7.11, "multiplicity": "s, br.", "integration": 2, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 7.32, "deltaTo": 7.75, "multiplicity": "m", "integration": 4, "assignment": "Ar-H" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 75, "peaks": [ { "delta": 2.23, "assignment": "CH3" }, { "delta": 2.42, "assignment": "CH3" }, { "delta": 2.5, "assignment": "br., D2O-exchangeable, NH2" }, { "delta": 2.84, "assignment": "CH3" }, { "delta": 3.47, "assignment": "CH3" }, { "delta": 7.11, "assignment": "br., D2O-exchangeable, NH2" }, { "delta": 7.32, "assignment": "m, Ar-H" }, { "delta": 7.75, "assignment": "m, Ar-H" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "5-[1-((3-Amino-4-methyl-5-(4-methylphenyldiazenyl)thiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazol (6b). Red solid (68%); mp 216–218°C; IR (KBr): ν 3407, 3317, 3113 (2NH2), 1636 (C=N), 1556 (N=N) cm−1; 1H-NMR (DMSO-d6): δ 2.23 (s, 3H, CH3), 2.42 (s, 3H, CH3), 2.50 (s, br., 2H, D2O-exchangeable, NH2), 2.84(s, 3H, CH3), 3.47 (s, 3H, CH3), 7.11 (s, br., 2H, D2O-exchangeable, NH2), 7.32–7.75 (m, 4H, Ar-H); MS m/z (%): 402 (M+ + 1, 11), 401 (M+ + 1, 18), 400 (M+, 29), 233 (19), 153 (69), 105 (100). Anal. Calcd. for C17H20N8S2 (400.52): C, 50.98; H, 5.03; N, 27.98. Found C, 50.68; H, 5.00; N, 27.69%.", "doi": "10.3390/molecules21010003" } }, { "name": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(nitrophenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14f)", "molecularFormula": "C16H16N8O2S2", "appearance": "Red solid", "yield": 78, "mp": { "low": 183, "high": 185, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": 3375, "assignment": "NH2, NH" }, { "wavenumber": 3194, "assignment": "NH2, NH" }, { "wavenumber": 1643, "assignment": "C=N" } ] }, "mass": { "peaks": [ { "mass": 417, "intensity": 3, "assignment": "M+ + 1" }, { "mass": 416, "intensity": 3, "assignment": "M+" }, { "mass": 153, "intensity": 33 }, { "mass": 113, "intensity": 24 }, { "mass": 43, "intensity": 100 } ] }, "hrms": { "found": 26.64, "expected": 26.9 }, "bp": { "units": "" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": 0, "peaks": [ { "deltaFrom": 2.42, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 2.54, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 3.57, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 6.91, "deltaTo": 7.38, "multiplicity": "m", "assignment": "4H, Ar-H" }, { "deltaFrom": 7.59, "multiplicity": "s", "assignment": "2H, D2O-exchangeable, NH2" }, { "deltaFrom": 10.53, "multiplicity": "s", "assignment": "1H, D2O-exchangeable, NH" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 0, "peaks": [ { "delta": 16.45, "assignment": "CH3" }, { "delta": 17.29, "assignment": "CH3" }, { "delta": 19.76, "assignment": "CH3" }, { "delta": 114.54 }, { "delta": 119.53 }, { "delta": 122.31 }, { "delta": 129.6 }, { "delta": 138.91 }, { "delta": 144.23 }, { "delta": 153.92, "assignment": "Ar-C" }, { "delta": 161.34 }, { "delta": 168.55 }, { "delta": 169.36 }, { "delta": 176.75, "assignment": "C=N" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(nitrophenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14f). Red solid (78%); mp 183–185°C; IR (KBr): v 3375, 3194 (NH2, NH), 1643 (C=N) cm−1; 1H-NMR (DMSO-d6): δ 2.42 (s, 3H, CH3), 2.54 (s, 3H, CH3), 3.57 (s, 3H, CH3), 6.91–7.38 (m, 4H, Ar-H), 7.59 (s, 2H, D2O-exchangeable, NH2), 10.53 (s, 1H, D2O-exchangeable, NH); 13C-NMR (DMSO-d6): δ 16.45 (CH3), 17.29 (CH3), 19.76 (CH3), 114.54, 119.53, 122.31, 129.60, 138.91, 144.23, 153.92 (Ar-C), 161.34, 168.55, 169.36, 176.75 (C=N); MS m/z (%): 417 (M+ + 1, 3), 416 (M+, 3), 153 (33), 113 (24), 43 (100). Anal. Calcd. for C16H16N8O2S2 (416.48): C, 46.14; H, 3.87; N, 26.90. Found C, 46.11; H, 3.76; N, 26.64%.", "doi": "10.3390/molecules21010003" } }, { "name": "5-[1-((3-Amino-5-((4-chlorophenyl)diazenyl)-4-methylthiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazole (6c)", "yield": 65, "molecularFormula": "C16H17ClN8S2", "appearance": "Red solid", "ir": { "peaks": [ { "wavenumber": 3409, "assignment": "2NH2" }, { "wavenumber": 3312, "assignment": "2NH2" }, { "wavenumber": 3151, "assignment": "2NH2" }, { "wavenumber": 1637, "assignment": "C=N" }, { "wavenumber": 1553, "assignment": "N=N" } ] }, "mass": { "peaks": [ { "mass": 422, "intensity": 2 }, { "mass": 421, "intensity": 4 }, { "mass": 420, "intensity": 10 }, { "mass": 299, "intensity": 17 }, { "mass": 244, "intensity": 43 }, { "mass": 212, "intensity": 46 }, { "mass": 155, "intensity": 52 }, { "mass": 113, "intensity": 85 }, { "mass": 72, "intensity": 100 } ] }, "hrms": { "expected": 420.94, "found": 420 }, "bp": { "low": null, "high": null, "units": null, "pressure": null, "pressureUnits": null }, "mp": { "low": 243, "high": 245, "units": "°C" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "deltaFrom": 2.43, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 2.52, "multiplicity": "s, br.", "assignment": "2H, D2O-exchangeable, NH2" }, { "deltaFrom": 2.86, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 3.49, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 7.35, "multiplicity": "s, br.", "assignment": "2H, D2O-exchangeable, NH2" }, { "deltaFrom": 7.38, "deltaTo": 7.83, "multiplicity": "m", "assignment": "4H, Ar-H" } ] }, "nmr13C": { "solvent": null, "frequency": null, "peaks": [ { "delta": null, "assignment": null } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "5-[1-((3-Amino-5-((4-chlorophenyl)diazenyl)-4-methylthiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazole (6c). Red solid (65%); mp 243–245 °C; IR (KBr): ν 3409, 3312, 3151 (2NH2), 1637 (C=N), 1553 (N=N) cm−1; 1H-NMR (DMSO-d6): δ 2.43 (s, 3H, CH3), 2.52 (s, br., 2H, D2O-exchangeable, NH2), 2.86 (s, 3H, CH3), 3.49 (s, 3H, CH3), 7.35 (s, br., 2H, D2O-exchangeable, NH2), 7.38-7.83 (m, 4H, Ar-H); MS m/z (%): 422 (M+ + 2, 2), 421 (M+ + 1, 4), 420 (M+, 10), 299 (17), 244 (43), 212 (46), 155 (52), 113 (85), 72 (100). Anal. Calcd. for C16H17ClN8S2 (420.94): C, 45.65; H, 4.07; N, 26.62. Found C, 45.60; H, 4.14; N, 26.38%.", "doi": "10.3390/molecules21010003" } }, { "name": "5-[1-((3-Amino-5-(4-bromophenyl)diazenyl)-4-methylthiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazol (6d)", "yield": 66, "molecularFormula": "C16H17BrN8S2", "appearance": "Red solid", "mp": { "low": 218, "high": 219, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": 3409, "assignment": "2NH2" }, { "wavenumber": 3294, "assignment": "2NH2" }, { "wavenumber": 3113, "assignment": "2NH2" }, { "wavenumber": 1632, "assignment": "C=N" }, { "wavenumber": 1557, "assignment": "N=N" } ] }, "mass": { "peaks": [ { "mass": 467, "intensity": 15 }, { "mass": 466, "intensity": 19 }, { "mass": 465, "intensity": 21 }, { "mass": 405, "intensity": 14 }, { "mass": 299, "intensity": 19 }, { "mass": 153, "intensity": 86 }, { "mass": 113, "intensity": 62 }, { "mass": 65, "intensity": 100 } ] }, "hrms": { "expected": 465.39, "found": 465.12 }, "nmr1H": { "solvent": "DMSO-d6", "frequency": 300, "peaks": [ { "deltaFrom": 2.46, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 2.51, "multiplicity": "s, br.", "integration": 2, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 2.85, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 3.47, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 7.26, "multiplicity": "s, br.", "integration": 2, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 7.3, "deltaTo": 7.81, "multiplicity": "m", "integration": 4, "assignment": "Ar-H" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 75, "peaks": [ { "delta": 65 }, { "delta": 113 }, { "delta": 153 }, { "delta": 299 }, { "delta": 405 } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "5-[1-((3-Amino-5-(4-bromophenyl)diazenyl)-4-methylthiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazol (6d). Red solid (66%); mp 218–219 °C; IR (KBr): ν 3409, 3294, 3113 (2NH2), 1632 (C=N), 1557 (N=N) cm−1; 1H-NMR (DMSO-d6): δ 2.46 (s, 3H, CH3), 2.51 (s, br., 2H, D2O-exchangeable, NH2), 2.85 (s, 3H, CH3), 3.47 (s, 3H, CH3), 7.26 (s, br., 2H, D2O-exchangeable, NH2), 7.30–7.81 (m, 4H, Ar-H); MS m/z (%): 467 (M+ + 2, 15), 466 (M+ + 1, 19), 465 (M+, 21), 405 (14), 299 (19), 153 (86), 113 (62), 65 (100). Anal. Calcd. for C16H17BrN8S2 (465.39): C, 41.29; H, 3.68; N, 24.08. Found C, 41.11; H, 3.57; N, 24.01%.", "doi": "10.3390/molecules21010003" } }, { "name": "5-[1-((3-Amino-5-(4-methoxyphenyl)diazenyl)-4-methylthiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazol (6e)", "yield": 68, "molecularFormula": "C17H20N8OS2", "appearance": "Red solid", "ir": { "peaks": [ { "wavenumber": 3403, "assignment": "2NH2" }, { "wavenumber": 3298, "assignment": "2NH2" }, { "wavenumber": 3117, "assignment": "2NH2" }, { "wavenumber": 1635, "assignment": "C=N" }, { "wavenumber": 1555, "assignment": "N=N" } ] }, "mass": { "peaks": [ { "mass": 416, "intensity": 4, "assignment": "M+" }, { "mass": 322, "intensity": 13 }, { "mass": 273, "intensity": 12 }, { "mass": 182, "intensity": 61 }, { "mass": 124, "intensity": 100 }, { "mass": 109, "intensity": 99 } ] }, "hrms": { "expected": 416.52, "found": 416.41 }, "bp": { "low": null, "high": null }, "mp": { "low": 212, "high": 214, "units": "°C" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "deltaFrom": 2.43, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 2.5, "multiplicity": "s", "integration": null, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 2.81, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 3.41, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 3.64, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 7.12, "multiplicity": "s", "integration": null, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 7.24, "deltaTo": 7.72, "multiplicity": "m", "integration": 4, "assignment": "Ar-H" } ] }, "nmr13C": { "solvent": null, "frequency": null, "peaks": [ { "delta": null, "assignment": null } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "5-[1-((3-Amino-5-(4-methoxyphenyl)diazenyl)-4-methylthiazol-2(3H)-ethylidene)hydrazono)]-2-amine-4-methyl-1,3-thiazol (6e). Red solid (68%); mp 212–214 °C; IR (KBr): ν 3403, 3298, 3117 (2NH2), 1635 (C=N), 1555 (N=N) cm−1; 1H-NMR (DMSO-d6): δ 2.43 (s, 3H, CH3), 2.50 (s, br., 2H, D2O-exchangeable, NH2), 2.81(s, 3H, CH3), 3.41 (s, 3H, CH3), 3.64 (s, 3H, CH3), 7.12 (s, br., 2H, D2O-exchangeable, NH2), 7.24-7.72 (m, 4H, Ar-H); MS m/z (%): 416 (M+, 4), 322 (13), 273 (12), 182 (61), 124 (100), 109 (99). Anal. Calcd. for C17H20N8OS2 (416.52): C, 49.02; H, 4.84; N, 26.90. Found C, 48.89; H, 4.76; N, 26.72%.", "doi": "10.3390/molecules21010003" } }, { "name": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(phenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14a)", "yield": 80, "molecularFormula": "C16H17N7S2", "appearance": "Red solid", "mp": { "low": 168, "high": 169, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": 3438, "assignment": "NH2, NH" }, { "wavenumber": 3283, "assignment": "NH2, NH" }, { "wavenumber": 1597, "assignment": "C=N" } ] }, "mass": { "peaks": [ { "mass": 372, "intensity": 4, "assignment": "M+ + 1" }, { "mass": 371, "intensity": 21, "assignment": "M+" }, { "mass": 218, "intensity": 29 }, { "mass": 153, "intensity": 100 }, { "mass": 78, "intensity": 90 }, { "mass": 42, "intensity": 79 } ] }, "hrms": { "expected": 371.48, "found": 371.7 }, "bp": { "low": null, "high": null, "units": null, "pressure": null, "pressureUnits": null }, "nmr1H": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "deltaFrom": 2.43, "multiplicity": "s", "integration": 3, "assignment": "3H, CH3" }, { "deltaFrom": 2.56, "multiplicity": "s", "integration": 3, "assignment": "3H, CH3" }, { "deltaFrom": 3.56, "multiplicity": "s", "integration": 3, "assignment": "3H, CH3" }, { "deltaFrom": 6.95, "deltaTo": 7.35, "multiplicity": "m", "integration": 5, "assignment": "5H, Ar-H" }, { "deltaFrom": 7.57, "multiplicity": "s", "integration": 2, "assignment": "2H, D2O-exchangeable, NH2" }, { "deltaFrom": 10.51, "multiplicity": "s", "integration": 1, "assignment": "1H, D2O-exchangeable, NH" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "delta": 16.87, "assignment": "CH3" }, { "delta": 17.29, "assignment": "CH3" }, { "delta": 19.39, "assignment": "CH3" }, { "delta": 114.58 }, { "delta": 119.46 }, { "delta": 122.31 }, { "delta": 129.69 }, { "delta": 138.97 }, { "delta": 144.14 }, { "delta": 153.95, "assignment": "Ar-C" }, { "delta": 161.24 }, { "delta": 168.59 }, { "delta": 169.31 }, { "delta": 176.75, "assignment": "C=N" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(phenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14a). Red solid (80%); mp 168–169 °C; IR (KBr): ν 3438, 3283 (NH2, NH), 1597 (C=N) cm−1; 1H-NMR (DMSO-d6): δ 2.43 (s, 3H, CH3), 2.56 (s, 3H, CH3), 3.56 (s, 3H, CH3), 6.95–7.35 (m, 5H, Ar-H), 7.57 (s, 2H, D2O-exchangeable, NH2), 10.51 (s, 1H, D2O-exchangeable, NH); 13C-NMR (DMSO-d6): δ 16.87 (CH3), 17.29 (CH3), 19.39 (CH3), 114.58, 119.46, 122.31, 129.69, 138.97, 144.14, 153.95 (Ar-C), 161.24, 168.59, 169.31, 176.75 (C=N); MS m/z (%): 372 (M+ + 1, 4), 371 (M+, 21), 218 (29), 153 (100), 78 (90), 42 (79). Anal. Calcd. for C16H17N7S2 (371.48): C, 51.73; H, 4.61; N, 26.39. Found C, 51.70; H, 4.46; N, 26.27%.", "doi": "10.3390/molecules21010003" } }, { "name": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(methylphenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14b)", "yield": 82, "molecularFormula": "C17H19N7S2", "appearance": "Red solid", "mp": { "low": 247, "high": 249, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": 3391, "assignment": "NH2, NH" }, { "wavenumber": 3278, "assignment": "NH2, NH" }, { "wavenumber": 1632, "assignment": "C=N" } ] }, "hrms": { "found": 385.51 }, "mass": { "peaks": [ { "mass": 16.85, "assignment": "CH3" }, { "mass": 17.28, "assignment": "CH3" }, { "mass": 19.39, "assignment": "CH3" }, { "mass": 20.83, "assignment": "CH3" }, { "mass": 114.59 }, { "mass": 119.48 }, { "mass": 130.12 }, { "mass": 131.28 }, { "mass": 138.34 }, { "mass": 141.83 }, { "mass": 153.86, "assignment": "Ar-C" }, { "mass": 161.04 }, { "mass": 168.69 }, { "mass": 169.26 }, { "mass": 176.58, "assignment": "C=N" } ] }, "bp": { "units": "" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": 300, "peaks": [ { "deltaFrom": 2.25, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 2.43, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 2.53, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 3.56, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 7.13, "multiplicity": "d", "couplings": [ 6.9 ], "assignment": "2H, Ar-H" }, { "deltaFrom": 7.26, "multiplicity": "d", "couplings": [ 6.9 ], "assignment": "2H, Ar-H" }, { "deltaFrom": 7.55, "multiplicity": "s", "integration": 2, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 10.44, "multiplicity": "s", "integration": 1, "assignment": "D2O-exchangeable, NH" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 75, "peaks": [ { "delta": 16.85, "assignment": "CH3" }, { "delta": 17.28, "assignment": "CH3" }, { "delta": 19.39, "assignment": "CH3" }, { "delta": 20.83, "assignment": "CH3" }, { "delta": 114.59 }, { "delta": 119.48 }, { "delta": 130.12 }, { "delta": 131.28 }, { "delta": 138.34 }, { "delta": 141.83 }, { "delta": 153.86, "assignment": "Ar-C" }, { "delta": 161.04 }, { "delta": 168.69 }, { "delta": 169.26 }, { "delta": 176.58, "assignment": "C=N" } ] }, "ms": { "peaks": [ { "mass": 386, "intensity": 12 }, { "mass": 385, "intensity": 36 }, { "mass": 232, "intensity": 53 }, { "mass": 153, "intensity": 85 }, { "mass": 113, "intensity": 100 } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(methylphenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14b). Red solid (82%); mp 247–249 °C; IR (KBr): ν 3391, 3278 (NH2, NH), 1632 (C=N) cm−1; 1H-NMR (DMSO-d6): δ 2.25 (s, 3H, CH3), 2.43 (s, 3H, CH3), 2.53 (s, 3H, CH3), 3.56 (s, 3H, CH3), 7.13 (d, 2H, J = 6.9 Hz, Ar-H), 7.26 (d, 2H, J = 6.9 Hz, Ar-H), 7.55 (s, 2H, D2O-exchangeable, NH2), 10.44 (s, 1H, D2O-exchangeable, NH); 13C-NMR (DMSO-d6): δ 16.85 (CH3), 17.28 (CH3), 19.39 (CH3), 20.83 (CH3), 114.59, 119.48, 130.12, 131.28, 138.34, 141.83, 153.86 (Ar-C), 161.04, 168.69, 169.26, 176.58 (C=N); MS m/z (%): 386 (M+ + 1, 12), 385 (M+, 36), 232 (53), 153 (85), 113 (100). Anal. Calcd. for C17H19N7S2 (385.51): C, 52.96; H, 4.97; N, 25.43. Found C, 52.91; H, 4.86; N, 25.33%.", "doi": "10.3390/molecules21010003" } }, { "name": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(chlorophenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14c)", "yield": 75, "molecularFormula": "C16H16ClN7S2", "appearance": "Red solid", "mp": { "low": 178, "high": 180, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": 3996, "assignment": "NH2, NH" }, { "wavenumber": 3283 }, { "wavenumber": 1632, "assignment": "C=N" }, { "wavenumber": 1606 } ] }, "mass": { "peaks": [ { "mass": 407, "intensity": 5, "assignment": "M+ + 1" }, { "mass": 406, "intensity": 18, "assignment": "M+" }, { "mass": 252, "intensity": 18 }, { "mass": 153, "intensity": 99 }, { "mass": 112, "intensity": 95 }, { "mass": 72, "intensity": 100 } ] }, "hrms": { "expected": 405.93, "found": 405.93 }, "bp": { "units": "°C" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": 10.57, "peaks": [ { "deltaFrom": 2.43, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 2.57, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 3.56, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 7.34, "multiplicity": "s", "integration": 4, "assignment": "Ar-H" }, { "deltaFrom": 7.57, "multiplicity": "s", "integration": 2, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 10.57, "multiplicity": "s", "integration": 1, "assignment": "D2O-exchangeable, NH" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 161.53, "peaks": [ { "delta": 16.87, "assignment": "CH3" }, { "delta": 17.29, "assignment": "CH3" }, { "delta": 19.43, "assignment": "CH3" }, { "delta": 116.04 }, { "delta": 119.41 }, { "delta": 125.79 }, { "delta": 129.55 }, { "delta": 139.81 }, { "delta": 143.13 }, { "delta": 154.26, "assignment": "Ar-C" }, { "delta": 168.31 }, { "delta": 169.38 }, { "delta": 176.77, "assignment": "C=N" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(chlorophenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14c). Red solid (75%); mp 178–180 °C; IR (KBr): ν 3996, 3283 (NH2, NH), 1632, 1606 (C=N) cm−1; 1H-NMR (DMSO-d6): δ 2.43 (s, 3H, CH3), 2.57 (s, 3H, CH3), 3.56 (s, 3H, CH3), 7.34 (s, 4H, Ar-H), 7.57 (s, 2H, D2O-exchangeable, NH2), 10.57 (s, 1H, D2O-exchangeable, NH); 13C-NMR (DMSO-d6): δ 16.87 (CH3), 17.29 (CH3), 19.43 (CH3), 116.04, 119.41, 125.79, 129.55, 139.81, 143.13, 154.26 (Ar-C), 161.53, 168.31, 169.38, 176.77 (C=N); MS m/z (%): 407 (M+ + 1, 5), 406 (M+, 18), 252 (18), 153 (99). 112 (95), 72 (100). Anal. Calcd. for C16H16ClN7S2 (405.93): C, 47.34; H, 3.97; N, 24.15. Found C, 47.39; H, 3.90; N, 24.06%.", "doi": "10.3390/molecules21010003" } }, { "name": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(bromophenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole", "yield": 75, "molecularFormula": "C16H16BrN7S2", "appearance": "Red solid", "mp": { "low": 176, "high": 178, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": 3368, "assignment": "NH2" }, { "wavenumber": 3191, "assignment": "NH" }, { "wavenumber": 1632, "assignment": "C=N" } ] }, "mass": { "peaks": [ { "mass": 452, "intensity": 2, "assignment": "M+ + 1" }, { "mass": 451, "intensity": 15, "assignment": "M+" }, { "mass": 296, "intensity": 14 }, { "mass": 153, "intensity": 100 }, { "mass": 113, "intensity": 86 }, { "mass": 72, "intensity": 98 } ] }, "hrms": { "found": 21.65 }, "bp": {}, "nmr1H": { "solvent": "DMSO-d6", "frequency": 0, "peaks": [ { "deltaFrom": 2.42, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 2.53, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 3.59, "multiplicity": "s", "assignment": "3H, CH3" }, { "deltaFrom": 7.28, "multiplicity": "d", "couplings": [ 4.5 ], "assignment": "2H, J = 4.5 Hz, Ar-H" }, { "deltaFrom": 7.48, "multiplicity": "d", "couplings": [ 4.5 ], "assignment": "2H, J = 4.5 Hz, Ar-H" }, { "deltaFrom": 7.58, "multiplicity": "s", "assignment": "2H, D2O-exchangeable, NH2" }, { "deltaFrom": 10.58, "multiplicity": "s", "assignment": "1H, D2O-exchangeable, NH" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 0, "peaks": [ { "delta": 16.87, "assignment": "CH3" }, { "delta": 17.3, "assignment": "CH3" }, { "delta": 19.43, "assignment": "CH3" }, { "delta": 113.65 }, { "delta": 116.48 }, { "delta": 119.42 }, { "delta": 132.55 }, { "delta": 139.91 }, { "delta": 143.53 }, { "delta": 154.25, "assignment": "Ar-C" }, { "delta": 161.53 }, { "delta": 168.29 }, { "delta": 169.38 }, { "delta": 176.75, "assignment": "C=N" } ] }, "meta": { "molfile": "Message:\nopenmolecules.org MolfileCreator 1.0\n\n 26 28 0 0 0 0 0 0 0 0999 V2000\n 6.0413 -0.7319 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0468 -0.8364 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3776 -0.0933 -0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4641 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5686 -1.4945 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5468 -1.7024 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8255 -2.1637 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7321 -0.5000 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 -0.0000 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9135 -0.0933 -0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5827 -0.8364 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0827 -1.7024 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.1045 -1.4945 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.4894 -2.6160 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5772 -0.7319 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.9839 0.1817 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.9785 0.2862 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3852 1.1997 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.3797 1.3043 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.9675 0.4953 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.5608 -0.4183 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.5662 -0.5228 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7974 2.0088 -0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 2 0 0 0 0\n 5 6 1 0 0 0 0\n 2 6 2 0 0 0 0\n 5 7 1 0 0 0 0\n 4 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 8 10 2 3 0 0 0\n 10 11 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 1 0 0 0 0\n 14 15 2 0 0 0 0\n 15 16 1 0 0 0 0\n 12 16 2 0 0 0 0\n 15 17 1 0 0 0 0\n 14 18 1 0 0 0 0\n 18 19 2 3 0 0 0\n 19 20 1 0 0 0 0\n 20 21 2 0 0 0 0\n 21 22 1 0 0 0 0\n 22 23 2 0 0 0 0\n 23 24 1 0 0 0 0\n 24 25 2 0 0 0 0\n 20 25 1 0 0 0 0\n 21 26 1 0 0 0 0\nM END\n\n", "ocl": { "idCode": "fegxC@B\\mxOY`qEAAPcHhhdmheDThieDpQkM{A@eMUMSUB`@@", "coordinates": "!BKF_MsxANosDlYrqgs\\~@Sk|qJxS}m|?Mwz[Rs{\\Bm?vw@k_}?`COtcF?J{o_fXPkotx", "index": [ -271060146, 369460225, 469827596, 952115465, -2136440828, 2097408, 287588356, -2012741619, 135794720, 36306978, 1310976, 134550592, -2146434556, 1318912, 4202496, 1590466 ] }, "mfInfo": { "mass": 450.37885148554113, "charge": 0, "mf": "C16H16BrN7S2", "atoms": { "C": 16, "H": 16, "Br": 1, "N": 7, "S": 2 }, "monoisotopicMass": 449.00919849548995, "unsaturation": 12 } }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(bromophenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14d). Red solid (75%); mp 176–178 °C; IR (KBr): ν 3368, 3191 (NH2, NH), 1632 (C=N) cm−1; 1H-NMR (DMSO-d6): δ 2.42 (s, 3H, CH3), 2.53 (s, 3H, CH3), 3.59 (s, 3H, CH3), 7.28 (d, 2H, J = 4.5 Hz, Ar-H), 7.48(d, 2H, J = 4.5 Hz, Ar-H), 7.58 (s, 2H, D2O-exchangeable, NH2), 10.58 (s, 1H, D2O-exchangeable, NH); 13C-NMR (DMSO-d6): δ 16.87 (CH3), 17.30 (CH3), 19.43 (CH3), 113.65, 116.48, 119.42, 132.55, 139.91, 143.53, 154.25 (Ar-C), 161.53, 168.29, 169.38, 176.75 (C=N); MS m/z (%): 452 (M+ + 1, 2), 451 (M+, 15), 296 (14), 153 (100), 113 (86), 72 (98). Anal. Calcd. for C16H16BrN7S2 (450.38): C, 42.67; H, 3.58; N, 21.77. Found C, 42.55; H, 3.67; N, 21.65%.", "doi": "10.3390/molecules21010003" } }, { "name": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(methoxylphenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14e)", "yield": 78, "molecularFormula": "C17H19N7OS2", "appearance": "Red solid", "mp": { "low": 187, "high": 189, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": 3414, "assignment": "NH2, NH" }, { "wavenumber": 3202, "assignment": "NH2, NH" }, { "wavenumber": 1624, "assignment": "C=N" } ] }, "nmr1H": { "solvent": "DMSO-d6", "frequency": 0, "peaks": [ { "deltaFrom": 2.43, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 2.53, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 3.56, "multiplicity": "s", "integration": 3, "assignment": "CH3" }, { "deltaFrom": 3.72, "multiplicity": "s", "integration": 3, "assignment": "OCH3" }, { "deltaFrom": 6.91, "deltaTo": 7.3, "multiplicity": "m", "integration": 4, "assignment": "Ar-H" }, { "deltaFrom": 7.87, "multiplicity": "s", "integration": 2, "assignment": "D2O-exchangeable, NH2" }, { "deltaFrom": 10.48, "multiplicity": "s", "integration": 1, "assignment": "D2O-exchangeable, NH" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 0, "peaks": [ { "delta": 8.93, "assignment": "CH3" }, { "delta": 16.85, "assignment": "CH3" }, { "delta": 17.19, "assignment": "CH3" }, { "delta": 55.73, "assignment": "OCH3" }, { "delta": 115.07 }, { "delta": 115.87 }, { "delta": 119.38 }, { "delta": 137.6 }, { "delta": 137.74 }, { "delta": 155.3 }, { "delta": 160.59, "assignment": "Ar-C" }, { "delta": 169.08 }, { "delta": 169.21 }, { "delta": 169.26 }, { "delta": 176.6, "assignment": "C=N" } ] }, "mass": { "peaks": [ { "mass": 402, "intensity": 1, "assignment": "M+ + 1, 2" }, { "mass": 401, "intensity": 13, "assignment": "M+" }, { "mass": 248, "intensity": 17 }, { "mass": 153, "intensity": 38 }, { "mass": 113, "intensity": 42 }, { "mass": 44, "intensity": 100 } ] }, "hrms": { "found": 401.51 }, "bp": { "units": "", "pressureUnits": "", "low": null, "high": null }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Amino-4-methyl-5-(1-(2-(4-methyl-5-(methoxylphenyldiazenyl)thiazol-2-yl)hydrazono)ethyl)thiazole (14e). Red solid (78%); mp 187–189 °C; IR (KBr): ν 3414, 3202 (NH2, NH), 1624 (C=N) cm−1; 1H-NMR (DMSO-d6): δ 2.43 (s, 3H, CH3), 2.53 (s, 3H, CH3), 3.56 (s, 3H, CH3), 3.72 (s, 3H, OCH3), 6.91–7.30 (m, 4H, Ar-H), 7.87 (s, 2H, D2O-exchangeable, NH2), 10.48 (s, 1H, D2O-exchangeable, NH); 13C-NMR (DMSO-d6): δ 8.93 (CH3), 16.85 (CH3), 17.19 (CH3), 55.73 (OCH3), 115.07, 115.87, 119.38, 137.60, 137.74, 155.30, 160.59 (Ar-C), 169.08, 169.21, 169.26, 176.60 (C=N); MS m/z (%): 402 (M+ + 1, 2), 401 (M+, 13), 248 (17), 153 (38), 113 (42), 44 (100). Anal. Calcd. for C17H19N7OS2 (401.51): C, 50.85; H, 4.77; N, 24.42. Found C, 50.82; H, 4.65; N, 24.23%.", "doi": "10.3390/molecules21010003" } }, { "name": "28,28,30-Trihydroxylupeol (1)", "appearance": "White powder (20.0 mg)", "mp": { "low": 222, "high": 224, "units": "°C" }, "uv": { "peaks": [ { "wavelength": 272 }, { "wavelength": 210 } ] }, "ir": { "peaks": [ { "wavenumber": 3310 }, { "wavenumber": 2920 }, { "wavenumber": 2158 }, { "wavenumber": 2042 }, { "wavenumber": 1976 }, { "wavenumber": 1611 }, { "wavenumber": 1411 }, { "wavenumber": 1021 } ] }, "mass": { "peaks": [ { "mass": 463.3393 }, { "mass": 931.7436 } ] }, "hrms": { "expected": 474.1465, "found": 474.1465 }, "molecularFormula": "C30H50O4", "nmr1H": { "solvent": "CDCl3", "frequency": 400, "peaks": [ { "deltaFrom": 0.79, "multiplicity": "s", "assignment": "H-23" }, { "deltaFrom": 0.83, "multiplicity": "s", "assignment": "H-24" }, { "deltaFrom": 0.94, "multiplicity": "s", "assignment": "H-25" }, { "deltaFrom": 1.01, "multiplicity": "s", "assignment": "H-26" }, { "deltaFrom": 1.07, "multiplicity": "s", "assignment": "H-27" }, { "deltaFrom": 0.88, "multiplicity": "m", "assignment": "H-9" }, { "deltaFrom": 1.26, "multiplicity": "m", "assignment": "H-15, H-16" }, { "deltaFrom": 1.28, "multiplicity": "m", "couplings": [ 6.6 ], "assignment": "H-6, H-7" }, { "deltaFrom": 1.32, "multiplicity": "m", "couplings": [ 7.2 ], "assignment": "H-5" }, { "deltaFrom": 1.34, "multiplicity": "m", "assignment": "H-22, H-13" }, { "deltaFrom": 1.61, "multiplicity": "m", "assignment": "H-11" }, { "deltaFrom": 1.68, "multiplicity": "m", "couplings": [ 3 ], "assignment": "H-2, H-12" }, { "deltaFrom": 1.88, "deltaTo": 1.94, "multiplicity": "m", "assignment": "H-21" }, { "deltaFrom": 2.04, "multiplicity": "m", "assignment": "H-18" }, { "deltaFrom": 2.38, "couplings": [ 7.2 ], "multiplicity": "d", "assignment": "H-19" }, { "deltaFrom": 3.39, "couplings": [ 10.8, 4.8 ], "multiplicity": "dd", "assignment": "H-3" }, { "deltaFrom": 4.57, "multiplicity": "br s", "assignment": "H-29" }, { "deltaFrom": 4.69, "multiplicity": "br s", "assignment": "H-29" }, { "deltaFrom": 4.79, "couplings": [ 6 ], "multiplicity": "t", "assignment": "H-28" }, { "deltaFrom": 5.14, "multiplicity": "m", "assignment": "H-30" }, { "deltaFrom": 5.19, "multiplicity": "m", "assignment": "H-30" } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": 100, "peaks": [ { "delta": 14.1, "assignment": "C-27" }, { "delta": 14.5, "assignment": "C-23" }, { "delta": 15.9, "assignment": "C-25" }, { "delta": 16.1, "assignment": "C-26" }, { "delta": 17.7, "assignment": "C-6" }, { "delta": 18, "assignment": "C-24" }, { "delta": 21, "assignment": "C-11" }, { "delta": 25.1, "assignment": "C-12" }, { "delta": 27.3, "assignment": "C-2" }, { "delta": 27.4, "assignment": "C-15" }, { "delta": 29.7, "assignment": "C-21" }, { "delta": 34.1, "assignment": "C-7" }, { "delta": 35.5, "assignment": "C-16" }, { "delta": 37.3, "assignment": "C-10" }, { "delta": 37.9, "assignment": "C-13" }, { "delta": 38.1, "assignment": "C-1" }, { "delta": 39.6, "assignment": "C-4" }, { "delta": 39.9, "assignment": "C-22" }, { "delta": 40.9, "assignment": "C-8" }, { "delta": 42.8, "assignment": "C-14" }, { "delta": 43, "assignment": "C-17" }, { "delta": 47.9, "assignment": "C-18" }, { "delta": 48.2, "assignment": "C-19" }, { "delta": 50.3, "assignment": "C-9" }, { "delta": 55.6, "assignment": "C-5" }, { "delta": 69.2, "assignment": "C-30" }, { "delta": 80.1, "assignment": "C-3" }, { "delta": 95.1, "assignment": "C-28" }, { "delta": 109.3, "assignment": "C-29" }, { "delta": 150.9, "assignment": "C-20" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "28,28,30-Trihydroxylupeol (1): White powder (20.0 mg), melting point 222–224 °C, UV λmax (C2H5OH) nm: 272, 210 (log ε 3.4, 2.2). IR λmax (CHCl3) cm−1: 3310, 2920, 2158, 2042, 1976, 1611, 1411, 1021. 1H-NMR (CDCl3): δH 0.79 (s, 3H, H-23), 0.83 (s, 3H, H-24), 0.94 (s, 3H, H-25), 1.01 (s, 3H, H-26), 1.07 (s, 3H, H-27), 0.88 (m, 10H, H-9), 1.26 (m, 4H, H-15, H-16), 1.28 (m, 4H, J = 6.6 Hz, H-6, H-7), 1.32 (m, 1H, J = 7.2 Hz, H-5), 1.34 (m, 4H, H-22, H-13), 1.61 (m, 4H, H-11), 1.68 (m, 4H, J = 3.0 Hz, H-2, H-12), 1.88–1.94 (m, 2H, H-21), 2.04 (m, 1H, H-18), 2.38 (d, 1H, J = 7.2 Hz, H-19), 3.39 (dd, 1H, J = 10.8, 4.8 Hz, H-3), 4.57 (br s, 1H, H-29), 4.69 (br s, 1H, H-29), 4.79 (t, 1H, J = 6.0 Hz, H-28), 5.14 (m, 1H, H-30) 5.19 (m, 1H, H-30). 13C-NMR (CDCl3): δC 14.1(C-27), 14.5 (C-23), 15.9 (C-25), 16.1 (C-26), 17.7 (C-6), 18.0 (C-24), 21.0 (C-11), 25.1 (C-12), 27.3 (C-2), 27.4 (C-15), 29.7 (C-21), 34.1 (C-7), 35.5 (C-16), 37.3 (C-10), 37.9 (C-13), 38.1 (C-1), 39.6 (C-4), 39.9 (C-22), 40.9 (C-8), 42.8 (C-14), 43.0 (C-17), 47.9 (C-18), 48.2 (C-19), 50.3 (C-9), 55.6 (C-5), 69.2 (C-30), 80.1(C-3), 95.1 (C-28), 109.3 (C-29), 150.9 (C-20). ESIMS m/z: 463.3393 [M + H − 12]+, 931.7436 [2M + H − 18]+, HRESIMS m/z: 474.1465 [M]+, calculated 474.1465 for molecular formula C30H50O4.", "doi": "10.3390/molecules21010009" } }, { "name": "3,21,21,26-Tetrahydroxylanostanoic acid (2)", "appearance": "White powder", "mp": { "low": 150, "high": 155, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": "1H-NMR", "peaks": [ { "deltaFrom": 0.8, "multiplicity": "s", "integration": 3, "assignment": "H-28" }, { "deltaFrom": 0.85, "multiplicity": "s", "integration": 1, "assignment": "H-29" }, { "deltaFrom": 0.92, "multiplicity": "q", "integration": 3, "assignment": "H-30" }, { "deltaFrom": 0.94, "deltaTo": 2.25, "multiplicity": "m", "assignment": null }, { "deltaFrom": 0.99, "multiplicity": "s", "integration": 2, "assignment": "H-18" }, { "deltaFrom": 1.01, "multiplicity": "m", "integration": 2, "assignment": "H-2" }, { "deltaFrom": 1.03, "multiplicity": "s", "integration": 1, "assignment": "H-19" }, { "deltaFrom": 1.18, "multiplicity": "m", "integration": 2, "assignment": "H-22" }, { "deltaFrom": 1.31, "multiplicity": "m", "integration": 2, "assignment": "H-12" }, { "deltaFrom": 1.34, "multiplicity": "m", "integration": 2, "assignment": "H-11" }, { "deltaFrom": 1.35, "multiplicity": "m", "integration": 2, "assignment": "H-23" }, { "deltaFrom": 1.48, "multiplicity": "m", "integration": 1, "assignment": "H-8, H-17" }, { "deltaFrom": 1.57, "multiplicity": "m", "integration": 2, "assignment": "H-15" }, { "deltaFrom": 1.63, "multiplicity": "m", "integration": 2, "assignment": "H-16" }, { "deltaFrom": 1.68, "multiplicity": "m", "integration": 1, "assignment": "H-20" }, { "deltaFrom": 1.77, "multiplicity": "m", "integration": 2, "assignment": "H-7" }, { "deltaFrom": 3.44, "multiplicity": "t", "integration": 1, "assignment": "H-3" }, { "deltaFrom": 4.03, "multiplicity": "d", "couplings": [ 12 ], "integration": 1, "assignment": "H-26" }, { "deltaFrom": 4.57, "multiplicity": "m", "integration": 1, "assignment": "H-24" }, { "deltaFrom": 4.79, "multiplicity": "t", "couplings": [ 6 ], "integration": 1, "assignment": "H-6" }, { "deltaFrom": 4.8, "multiplicity": "m", "integration": 1, "assignment": "H-21" } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": "13C-NMR", "peaks": [ { "delta": 29.8, "assignment": "C-1" }, { "delta": 25.7, "assignment": "C-2" }, { "delta": 80.1, "assignment": "C-3" }, { "delta": 43, "assignment": "C-4" }, { "delta": 151, "assignment": "C-5" }, { "delta": 109.3, "assignment": "C-6" }, { "delta": 31.9, "assignment": "C-7" }, { "delta": 50.3, "assignment": "C-8" }, { "delta": 48.2, "assignment": "C-9" }, { "delta": 39.9, "assignment": "C-10" }, { "delta": 23.7, "assignment": "C-11" }, { "delta": 22.7, "assignment": "C-12" }, { "delta": 42.8, "assignment": "C-13" }, { "delta": 40.9, "assignment": "C-14" }, { "delta": 34.5, "assignment": "C-15" }, { "delta": 29.4, "assignment": "C-16" }, { "delta": 55.6, "assignment": "C-17" }, { "delta": 27.4, "assignment": "C-18" }, { "delta": 17.7, "assignment": "C-19" }, { "delta": 35.3, "assignment": "C-20" }, { "delta": 95.1, "assignment": "C-21" }, { "delta": 35.5, "assignment": "C-22" }, { "delta": 25, "assignment": "C-23" }, { "delta": 150.9, "assignment": "C-24" }, { "delta": 109.3, "assignment": "C-25" }, { "delta": 69.2, "assignment": "C-26" }, { "delta": 173.8, "assignment": "C-27" }, { "delta": 14.1, "assignment": "C-28" }, { "delta": 15.9, "assignment": "C-29" }, { "delta": 16.5, "assignment": "C-30" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "3,21,21,26-Tetrahydroxylanostanoic acid (2): White powder (17.2 mg), melting point 150–155 °C, UV νmax (C2H5OH) nm: 272, 207 (log ε 2.3, 2.8). IR νmax (CHCl3) cm−1: 3215, 2915, 2850, 2134, 1985, 1735, 1678, 1642, 1472, 1120. ESIMS (negative mode) m/z: 502.3290 [M]+, 479.1023 [M − 23]+, 453.0885 [M − CH3OH − 17]+, and 311.1563 [M − side chain (C8H14O5) − 1]+, HRESIMS (positive mode) m/z: 503.3570 [M + H]+, calculated 502.3290 for molecular formula C30H50O. 1H-NMR (CDCl3): δH 0.80 (s, 3H, H-28), 0.85 (s, 1H, H-29), 0.92 (q, 3H, H-30), 0.94 (m, 2H), 0.99 (s, 2H, H-18), 1.01(m, 2H, H-2), 1.03 (s, 1H, H-19), 1.18 (m, 2H, H-22), 1.31 (m, 2H, H-12), 1.34 (m, 2H, H-11), 1.35 (m, 2H, H-23), 1.48 (m, 1H, H-8, H-17), 1.57 (m, 2H, H-15), 1.63 (m, 2H, H-16), 1.68 (m, 1H, H-20), 1.77 (m, 2H, H-7), 3.44 (t, 1H, H-3), 4.03 (d, 1H, J = 12.0 Hz, H-26), 4.57 (m,1H, H-24), 4.79 (t, 1H, J = 6.0 Hz, H-6), 4.80 (m, 1H, H-21), 2.25 (C-21), 2.30 (C-21), 4.68 (C-3), 4.69 (C-26). 13C-NMR (CDCl3): δC 29.8 (C-1), 25.7 (C-2), 80.1 (C-3), 43.0 (C-4), 151.0 (C-5), 109.3 (C-6), 31.9 (C-7), 50.3 (C-8), 48.2 (C-9), 39.9 (C-10), 23.7 (C-11), 22.7 (C-12), 42.8 (C-13), 40.9 (C-14), 34.5 (C-15), 29.4 (C-16), 55.6 (C-17), 27.4 (C-18), 17.7 (C-19), 35.3 (C-20), 95.1 (C-21), 35.5 (C-22), 25.0 (C-23), 150.9 (C-24), 109.3 (C-25), 69.2 (C-26), 173.8 (C-27), 14.1 (C-28), 15.9 (C-29), 16.5 (C-30).", "doi": "10.3390/molecules21010009" } }, { "name": "Pinostrobin", "molecularFormula": "C16H14O2", "appearance": "colorless crystals", "nmr1H": { "solvent": "CDCl3", "frequency": 500, "peaks": [ { "deltaFrom": 11.99, "multiplicity": "s", "assignment": "5-OH" }, { "deltaFrom": 7.45, "multiplicity": "m", "assignment": "H-2', H-3', H-4', H-5'" }, { "deltaFrom": 6.06, "multiplicity": "d", "couplings": [ 2.5 ], "assignment": "H-6" }, { "deltaFrom": 6.05, "multiplicity": "d", "couplings": [ 2.5 ], "assignment": "H-8" }, { "deltaFrom": 5.41, "multiplicity": "dd", "couplings": [ 13, 3 ], "assignment": "H-2" }, { "deltaFrom": 3.79, "multiplicity": "s", "assignment": "7-OMe" }, { "deltaFrom": 3.07, "multiplicity": "dd", "couplings": [ 17, 13 ], "assignment": "H-3" }, { "deltaFrom": 2.82, "multiplicity": "dd", "couplings": [ 17, 3 ], "assignment": "H-3" } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": 125, "peaks": [ { "delta": 79.2, "assignment": "C-2" }, { "delta": 43.41, "assignment": "C-3" }, { "delta": 195.73, "assignment": "C-4" }, { "delta": 162.79, "assignment": "C-5" }, { "delta": 95.2, "assignment": "C-6" }, { "delta": 167.8, "assignment": "C-7" }, { "delta": 94.3, "assignment": "C-8" }, { "delta": 164.17, "assignment": "C-9" }, { "delta": 138.39, "assignment": "C-1'" }, { "delta": 126.19, "assignment": "C2'/C-6'" }, { "delta": 128.9, "assignment": "C-3', C-4'/C-5'" }, { "delta": 55.69, "assignment": "OCH3" } ] }, "meta": { "molfile": "Message:\nopenmolecules.org MolfileCreator 1.0\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -0.0000 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0118 1.4988 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.3218 2.2541 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2746 2.2659 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.3454 3.7647 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6317 1.5106 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2510 3.7765 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0708 4.5318 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6554 4.5200 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6436 0.0354 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.9417 2.2659 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5255 4.5318 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.9535 3.7883 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8119 3.8001 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5019 6.0306 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2635 4.5436 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0865 4.5554 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7765 6.7977 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2753 6.0424 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0747 6.0660 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 2 4 1 0 0 0 0\n 3 5 2 0 0 0 0\n 3 6 1 0 0 0 0\n 4 7 1 0 0 0 0\n 5 8 1 0 0 0 0\n 5 9 1 0 0 0 0\n 6 10 1 0 0 0 0\n 6 11 2 0 0 0 0\n 7 12 1 6 0 0 0\n 9 13 2 0 0 0 0\n 12 14 2 0 0 0 0\n 12 15 1 0 0 0 0\n 13 16 1 0 0 0 0\n 14 17 1 0 0 0 0\n 15 18 2 0 0 0 0\n 16 19 1 0 0 0 0\n 17 20 2 0 0 0 0\n 7 8 1 0 0 0 0\n 11 13 1 0 0 0 0\n 18 20 1 0 0 0 0\nM END\n\n", "ocl": { "idCode": "fbm@P@@\\e{HhheEEcDddsbcQrtEDPDDPPYP@", "coordinates": "!B_hBH?M_|o`BH_[x@U?rH@g{_b@IW@db}u{v~`H`BUpIW?Gz@_`@", "index": [ -32969, 1848747681, 848298988, 1267215753, -728627648, 270938690, 285515972, 11537180, 286852160, 77619206, 1699910682, 1746960528, 537985312, 167777794, -2062548991, 289439748 ] }, "mfInfo": { "mass": 270.28056460181796, "charge": 0, "mf": "C16H14O4", "atoms": { "C": 16, "H": 14, "O": 4 }, "monoisotopicMass": 270.0892089295, "unsaturation": 10 } }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "Pinostrobin (5-hydroxy-7-methoxy-flavanone, 1): colorless crystals, molecular formula (C16H14O2) 1H-NMR (500 MHz, CDCl3): 11.99 (1 H, s, 5-OH), 7.45 ( 5 H, m, H-2’, H-3’, H-4’ e H-5’), 6.06 (1H, d, J = 2.5 Hz, H-6), 6.05 (1H, d, J = 2.5, H-8), 5.41 (1H, dd, J = 13.00 and 3.00 Hz, H-2), 3.79 (3H, s, 7-OMe), 3.07 (1H, dd,17.00Hz e 13.00, H-3), 2.82 (1H, dd, 17.00Hz, 3.00 Hz, H-3). 13C-NMR (125 MHz, CDCl3): 79.20 (C-2), 43.41 (C-3), 195.73 (C-4), 162.79 (C-5), 95.20 (C-6), 167.80 (C-7), 94.30 (C-8), 164.17 (C-9), 138.39 (C-1’), 126.19 (C2’/C-6’), 128.9 (C-3’, C-4’/C-5’), 55.69 (OCH3). ", "doi": "10.3390/molecules21010011" } }, { "name": "trans-Feruloyltyramine", "moleculeNumber": "10", "appearance": "pale amorphous solid", "molecularFormula": "C18H19NO4", "nmr1H": { "solvent": "DMSO-d6", "frequency": 400, "peaks": [ { "deltaFrom": 7.11, "multiplicity": "sl", "assignment": "H-2" }, { "deltaFrom": 6.78, "multiplicity": "d", "couplings": [ 8 ], "assignment": "H-5" }, { "deltaFrom": 6.98, "multiplicity": "d", "couplings": [ 8 ], "assignment": "H-7" }, { "deltaFrom": 7.3, "multiplicity": "d", "couplings": [ 16 ], "assignment": "H-7" }, { "deltaFrom": 6.43, "multiplicity": "d", "couplings": [ 15.8 ], "assignment": "H-8" }, { "deltaFrom": 7, "multiplicity": "d", "couplings": [ 8 ], "assignment": "H-2'/H-6'" }, { "deltaFrom": 6.68, "multiplicity": "d", "couplings": [ 8 ], "assignment": "H-3'/H-5'" }, { "deltaFrom": 2.64, "multiplicity": "t", "assignment": "H-7'" }, { "deltaFrom": 3.33, "multiplicity": "m", "assignment": "H-8'" }, { "deltaFrom": 3.79, "multiplicity": "s", "assignment": "OCH3" }, { "deltaFrom": 8.01, "multiplicity": "t", "assignment": "NH" } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 100, "peaks": [ { "delta": 126.93, "assignment": "C-1" }, { "delta": 111.12, "assignment": "C-2" }, { "delta": 148.37, "assignment": "C-3" }, { "delta": 148.75, "assignment": "C-4" }, { "delta": 116.18, "assignment": "C-5" }, { "delta": 122.09, "assignment": "C-6" }, { "delta": 139.56, "assignment": "C-7" }, { "delta": 119.53, "assignment": "C-8" }, { "delta": 128.19, "assignment": "C-1'" }, { "delta": 130.02, "assignment": "C-2'/C-6'" }, { "delta": 115.67, "assignment": "C-3'/C-5'" }, { "delta": 156.18, "assignment": "C-4'" }, { "delta": 34.27, "assignment": "C-7'" }, { "delta": 41.27, "assignment": "C-8'" }, { "delta": 56.07, "assignment": "OCH3" } ] }, "meta": { "molfile": "Message:\nopenmolecules.org MolfileCreator 1.0\n\n 23 24 0 0 0 0 0 0 0 0999 V2000\n 3.4641 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3301 -0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0622 -0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9282 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7942 -0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6603 -0.5000 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5263 -0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7942 1.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6603 1.5000 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9282 1.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0622 1.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4641 -1.5000 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7321 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 -0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.8660 0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 -1.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.8660 -2.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -1.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5981 -2.0000 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 2 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 6 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 9 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 4 12 1 0 0 0 0\n 1 13 2 0 0 0 0\n 1 14 1 0 0 0 0\n 14 15 1 0 0 0 0\n 15 16 1 0 0 0 0\n 16 17 1 0 0 0 0\n 17 18 2 0 0 0 0\n 18 19 1 0 0 0 0\n 19 20 2 0 0 0 0\n 20 21 1 0 0 0 0\n 21 22 2 0 0 0 0\n 17 22 1 0 0 0 0\n 20 23 1 0 0 0 0\nM END\n\n", "ocl": { "idCode": "fnc`P@D@cUjSJjsJk^kdaruMP@@PU@BAH", "coordinates": "!B?`BH@k\\BbOvw?X`BmpJH?[_}?`BH@oy?mpJw@hc}bOvw?_x@?g~w@k\\BbOt", "index": [ -3149478, 374449921, 268517518, 1082143105, -2137915392, 2097730, 810344964, -2147482604, 135266304, 2170882, 611451010, 2097152, -2147483136, 1073743361, 5308416, 557124 ] }, "mfInfo": { "mass": 313.34844337701315, "charge": 0, "mf": "C18H19NO4", "atoms": { "C": 18, "H": 19, "N": 1, "O": 4 }, "monoisotopicMass": 313.13140809508, "unsaturation": 10 } }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "trans-Feruloyltyramine (10): pale amorphous solid, molecular formula (C18H19NO4), 1H-NMR (δ, 400 MHz, DMSO-d6), 7.11 (1H, sl, H-2), 6.78 (1H, d, J = 8.0Hz, H-5), 6.98 (1H, d, J = 8.0 Hz, H-7), 7.30 (1H, d, J = 16Hz, H-7), 6.43, (1H, d, J = 15.8 Hz, H-8), 7.00 (2H, d, J = 8.0, H-2’/H-6’), 6.68 (2H, d, J = 8.0 Hz, H-3’/H-5’), 2.64 (2H, t, H-7’), 3.33 (2H, m, H-8’), 3.79 (3H, s, OCH3), 8.01 (1H, t, NH). 13C-NMR (δ, 100 MHz, DMSO-d6) 126.93 (C-1), 111.12 (C-2), 148.37 (C-3), 148.75 (C-4), 116.18 (C-5), 122,09 (C-6), 139.56 (C-7), 119.53 (C-8), 128.19 (C-1’), 130.02 (C-2’/C-6’), 115.67 (C-3’/C-5’), 156.18 (C-4’), 34.27 (C-7’), 41.27 (C-8’), 56.07 (OCH3).", "doi": "10.3390/molecules21010011" } }, { "name": "Methyl 4-[(E)-6-(4-methoxycarbonylphenyl)hex-3-en-1,5-diynyl]benzoate (E-11)", "nmr1H": { "solvent": "CDCl3", "frequency": 500, "peaks": [ { "deltaFrom": 8.01, "multiplicity": "AA'BB'", "integration": 4, "assignment": "Ar-H" }, { "deltaFrom": 7.52, "multiplicity": "AA'BB'", "integration": 4, "assignment": "Ar-H" }, { "deltaFrom": 6.33, "multiplicity": "s", "integration": 2, "assignment": "CH=CH" }, { "deltaFrom": 3.92, "integration": 6, "assignment": "OCH3" } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": 100.6, "peaks": [ { "delta": 166.4 }, { "delta": 129.9 }, { "delta": 129.6 }, { "delta": 129.5 }, { "delta": 127.3 }, { "delta": 120.1 }, { "delta": 94.5 }, { "delta": 89.8 }, { "delta": 52.3 } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "Methyl 4-[(E)-6-(4-methoxycarbonylphenyl)hex-3-en-1,5-diynyl]benzoate (E-11). 1H-NMR (500 MHz, CDCl3) δ = 8.01 (AA′BB′, 4H, Ar-H), 7.52 (AA′BB′, 4H, Ar-H), 6.33 (s, 2H, CH=CH), 3.92 (6H, OCH3). 13C-NMR (100.6 MHz, CDCl3) δ = 166.4, 129.9, 129.6, 129.5, 127.3, 120.1, 94.5, 89.8, 52.3.", "doi": "10.3390/molecules21010016" } }, { "name": "Ethyl (3Z)-3-(6-ethoxycarbonylindan-1-ylidene)indane-5-carboxylate (Z-16)", "nmr1H": { "solvent": "CDCl3", "frequency": 500, "peaks": [ { "deltaFrom": 8.76, "multiplicity": "d", "couplings": [ 1.6 ], "assignment": "H-4" }, { "deltaFrom": 7.89, "multiplicity": "dd", "couplings": [ 1.6, 7.9 ], "assignment": "H-6" }, { "deltaFrom": 7.35, "multiplicity": "dm", "couplings": [ 7.9 ], "assignment": "H-7" }, { "deltaFrom": 4.32, "multiplicity": "q", "couplings": [ 7.1 ], "assignment": "OCH2" }, { "deltaFrom": 3.04, "deltaTo": 3.04, "multiplicity": "m", "assignment": "CH2-1" }, { "deltaFrom": 2.85, "deltaTo": 2.85, "multiplicity": "m", "assignment": "CH2-2" }, { "deltaFrom": 1.31, "multiplicity": "t", "couplings": [ 7.1 ], "assignment": "OCH2CH3" } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": 100.6, "peaks": [ { "delta": 166.6, "assignment": "CO" }, { "delta": 153.3, "assignment": "C-7a" }, { "delta": 140.4, "assignment": "C-3a" }, { "delta": 135, "assignment": "C-3" }, { "delta": 128.9, "assignment": "C-6" }, { "delta": 128.3, "assignment": "C-5" }, { "delta": 125, "assignment": "C-7" }, { "delta": 124.2, "assignment": "C-4" }, { "delta": 60.7, "assignment": "COCH2" }, { "delta": 34.7, "assignment": "CH2-2" }, { "delta": 30.7, "assignment": "CH2-1" }, { "delta": 14.2, "assignment": "CH2CH3" } ] }, "mass": { "peaks": [ { "mass": 376 } ], "ionization": "EI" }, "hrms": { "expected": 376, "found": 376 }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "Ethyl (3Z)-3-(6-ethoxycarbonylindan-1-ylidene)indane-5-carboxylate (Z-16). Rf = 0.43 (dichloromethane). 1H-NMR (500 MHz, CDCl3) δ = 8.76 (2H, d, J = 1.6 Hz, H-4), 7.89 (2H, dd, J = 1.6, 7.9 Hz, H-6), 7.35 (2H, dm, J = 7.9, H-7), 4.32 (4H, q, J = 7.1 Hz, OCH2), 3.04 (4H, m, CH2-1), 2.85 (4H, m, CH2-2), 1.31 (6H, t, J = 7.1 Hz, OCH2CH3). 13C-NMR (100.6 MHz, CDCl3) δ = 166.6 (CO), 153.3 (C-7a), 140.4 (C-3a), 135.0 (C-3), 128.9 (C-6), 128.3 (C-5), 125.0 (C-7), 124.2 (C-4), 60.7 (COCH2), 34.7 (CH2-2), 30.7 (CH2-1), 14.2 (CH2CH3); MS m/z (EI) 376 [M + H]+.", "doi": "10.3390/molecules21010016" } }, { "name": "Z-Dicarboxylic acid Z-17", "moleculeNumber": null, "yield": 94, "molecularFormula": null, "appearance": null, "ir": { "peaks": [] }, "mass": { "peaks": [] }, "nmr1H": { "solvent": "dmso-d6", "frequency": 500, "peaks": [ { "deltaFrom": 8.54, "multiplicity": "d", "couplings": [ 1.5 ], "assignment": "H-4" }, { "deltaFrom": 7.79, "multiplicity": "dd", "couplings": [ 1.5, 7.8 ], "assignment": "H-6" }, { "deltaFrom": 7.46, "multiplicity": "dm", "couplings": [ 7.8 ] }, { "deltaFrom": 3.02, "multiplicity": "m" }, { "deltaFrom": 2.83, "multiplicity": "m" } ] }, "nmr13C": { "solvent": "dmso-d6", "frequency": 100.6, "peaks": [ { "delta": 167.6 }, { "delta": 153.7 }, { "delta": 140.33 }, { "delta": 135.3 }, { "delta": 129.2 }, { "delta": 129.1 }, { "delta": 125.9 }, { "delta": 123.8 }, { "delta": 34.7 }, { "delta": 30.6 } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "Z-Dicarboxylic acid Z-17 (96 mg, 94%). 1H-NMR (500 MHz, dmso-d6, 25 °C) δ = 8.54 (2H, d, J = 1.5 Hz, H-4), 7.79 (2H, dd, J = 1.5, 7.8 Hz, H-6), 7.46 (2H, dm, J = 7.8 Hz), 3.02 (4H, m), 2.83 (4H, m). 13C-NMR (100.6 MHz, dmso-d6) δ = 167.6, 153.7, 140.33, 135.3, 129.2, 129.1, 125.9, 123.8, 34.7, 30.6.", "doi": "10.3390/molecules21010016" } }, { "name": "E-Dicarboxylic acid E-17", "yield": 82, "molecularFormula": "C20H16O4", "appearance": "", "ir": { "peaks": [ { "wavenumber": 0 } ] }, "mass": { "peaks": [ { "mass": 0 } ] }, "hrms": { "expected": 321.1121, "found": 321.1118 }, "bp": { "units": "" }, "mp": { "units": "" }, "nmr1H": { "solvent": "dmso-d6", "frequency": 500, "peaks": [ { "deltaFrom": 8.17, "multiplicity": "d", "couplings": [ 1.5 ], "assignment": "H-4" }, { "deltaFrom": 7.84, "multiplicity": "dd", "couplings": [ 1.5, 7.8 ], "assignment": "H-6" }, { "deltaFrom": 7.48, "multiplicity": "d", "couplings": [ 7.8 ], "assignment": "H-7" }, { "deltaFrom": 3.18, "multiplicity": "m", "integration": 8, "assignment": "CH2CH2" } ] }, "nmr13C": { "solvent": "dmso-d6", "frequency": 75.5, "peaks": [ { "delta": 167.9, "assignment": "" }, { "delta": 152.7, "assignment": "" }, { "delta": 143.1, "assignment": "" }, { "delta": 135.5, "assignment": "" }, { "delta": 129.7, "assignment": "" }, { "delta": 129, "assignment": "" }, { "delta": 125.6, "assignment": "" }, { "delta": 125.5, "assignment": "" }, { "delta": 31.8, "assignment": "" }, { "delta": 31, "assignment": "" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "E-Dicarboxylic acid E-17 (83 mg, 82%). 1H-NMR (500 MHz, dmso-d6, 25 °C) δ = 8.17 (2H, d, J = 1.5 Hz, H-4), 7.84 (2H, dd, J = 1.5, 7.8 Hz, H-6), 7.48 (2H, d, J = 7.8 Hz, H-7), 3.18 (8H, m, CH2CH2). 13C-NMR (75.5 MHz, dmso-d6, 25 °C) δ = 167.9, 152.7, 143.1, 135.5, 129.7, 129.0, 125.6, 125.5, 31.8, 31.0. HRMS, calc. for C20H16O4: m/z = 321.1121 [M + H]+, found 321.1118.", "doi": "10.3390/molecules21010016" } }, { "name": "4-(4'-Chlorophenylamino)-7-fluoroquinoline (1b)", "yield": 92.93, "mp": { "low": 194, "high": 195, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 8.57, "multiplicity": "s", "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.96, "multiplicity": "dd", "couplings": [ 8.4, 6 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.7, "multiplicity": "d", "couplings": [ 10.2 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.41, "deltaTo": 7.4, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.31, "multiplicity": "t", "couplings": [ 8.4 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.27, "deltaTo": 7.25, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 6.9, "multiplicity": "d", "couplings": [ 4.8 ], "integration": 1, "assignment": "ArH" } ] }, "esi-ms": { "peaks": [ { "mass": 273.4, "intensity": 100, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(4′-Chlorophenylamino)-7-fluoroquinoline (1b). Yield: 92.93%. m.p. 194–195 °C, 1H-NMR (600 MHz, CDCl3) δ: 8.57 (s, 1H, ArH), 7.96 (dd, J = 8.4, 6.0 Hz, 1H, ArH), 7.70 (d, 1H, J = 10.2 Hz, ArH), 7.41–7.40 (m, 2H, ArH), 7.31 (t, J = 8.4 Hz, 1H, ArH), 7.27–7.25 (m, 2H, ArH), 6.90 (d, J = 4.8 Hz, 1H, ArH). ESI-MS (m/z): 273.4 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(3'-Fluorophenylamino)-7-fluoroquinoline", "yield": 95.37, "mp": { "low": 173, "high": 174, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 8.62, "multiplicity": "s", "assignment": "1H, ArH" }, { "deltaFrom": 7.94, "multiplicity": "dd", "couplings": [ 9, 6 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.7, "multiplicity": "dd", "couplings": [ 6.6, 2.1 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.38, "multiplicity": "dd", "couplings": [ 14.7, 8.1 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.34, "deltaTo": 7.31, "multiplicity": "m", "assignment": "1H, ArH" }, { "deltaFrom": 7.06, "multiplicity": "t", "couplings": [ 4.5 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.04, "deltaTo": 7.02, "multiplicity": "m", "assignment": "2H, ArH" }, { "deltaFrom": 6.91, "deltaTo": 6.88, "multiplicity": "m", "assignment": "1H, ArH" } ] }, "mass": { "peaks": [ { "mass": 257.4, "assignment": "[M + H]+" } ] }, "meta": { "molfile": "Message:\nopenmolecules.org MolfileCreator 1.0\n\n 19 21 0 0 0 0 0 0 0 0999 V2000\n 4.3301 -0.0000 -0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4641 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7321 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7321 -1.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -2.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4641 -1.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 -0.0000 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.8660 0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 -0.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 -1.5000 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.8660 -2.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.8660 -3.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -3.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 -3.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 -2.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -1.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -4.5000 -0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 2 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 2 7 2 0 0 0 0\n 4 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 15 1 0 0 0 0\n 15 16 2 0 0 0 0\n 16 17 1 0 0 0 0\n 17 18 2 0 0 0 0\n 9 18 1 0 0 0 0\n 13 18 1 0 0 0 0\n 15 19 1 0 0 0 0\nM END\n\n", "ocl": { "idCode": "fluPA@FZAHQdDfUmWYVirR`i`@@J@H@@@", "coordinates": "!B?`BH@k\\B?`C~@H`BmpK~@Ox@mpJw@k_}mpK~_{_}m?vw@oy?", "index": [ 151425032, 37814528, 132, 1073741824, -2146304000, 0, 2129936, 134217728, 0, 8192, 262400, 18432, 262144, 262144, 4, 526401 ] }, "mfInfo": { "mass": 256.2506587399381, "charge": 0, "mf": "C15H10F2N2", "atoms": { "C": 15, "H": 10, "F": 2, "N": 2 }, "monoisotopicMass": 256.08120465662, "unsaturation": 11 } }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(3′-Fluorophenylamino)-7-fluoroquinoline (1c). Yield: 95.37%; m.p. 173–174 °C; 1H-NMR (600 MHz, CDCl3) δ: 8.62 (s, 1H, ArH), 7.94 (dd, J = 9.0, 6.0 Hz, 1H, ArH), 7.70 (dd, J = 6.6, 2.1 Hz, 1H, ArH), 7.38 (dd, J = 14.7, 8.1 Hz, 1H, ArH), 7.34–7.31 (m, 1H, 1H, ArH), 7.06 (t, J = 4.5 Hz, 1H, ArH), 7.04–7.02 (m, 2H, ArH), 6.91–6.88 (m, 1H, ArH). ESI-MS (m/z): 257.4 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(3'-Chloro-4'-fluorophenylamino)-8-methoxyquinoline (2f)", "yield": 80.14, "mp": { "low": 247, "high": 249, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.59, "multiplicity": "d", "couplings": [ 5.1 ], "assignment": "ArH" }, { "deltaFrom": 7.38, "deltaTo": 7.36, "multiplicity": "m", "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.2, "deltaTo": 7.17, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.07, "multiplicity": "dd", "couplings": [ 6.6, 2.4 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 6.88, "multiplicity": "d", "couplings": [ 5.1 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 4.08, "multiplicity": "s", "integration": 3, "assignment": "OCH3" } ] }, "esims": { "peaks": [ { "mass": 303.3, "intensity": 1, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(3′-Chloro-4′-fluorophenylamino)-8-methoxyquinoline (2f). Yield: 80.14%; m.p.247–249 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.59 (d, J = 5.1 Hz, ArH), 7.38–7.36 (m, 1H, ArH), 7.20–7.17 (m, 2H, ArH), 7.07 (dd, J = 6.6, 2.4 Hz, 1H, ArH), 6.88 (d, J = 5.1 Hz, 1H, ArH), 4.08 (s, 3H, OCH3); ESI-MS (m/z): 303.3 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(4'-Methylphenylamino)-8-methoxyquinoline", "yield": 78.46, "mp": { "low": 258, "high": 260, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.56, "multiplicity": "d", "couplings": [ 5.4 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.43, "deltaTo": 7.47, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.22, "deltaTo": 7.17, "multiplicity": "m", "integration": 4, "assignment": "ArH" }, { "deltaFrom": 7.06, "multiplicity": "dd", "couplings": [ 6.9, 1.5 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 6.93, "multiplicity": "d", "couplings": [ 5.4 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 4.08, "multiplicity": "s", "integration": 3, "assignment": "OCH3" }, { "deltaFrom": 2.39, "multiplicity": "s", "integration": 3, "assignment": "CH3" } ] }, "ms": { "peaks": [ { "mass": 265.4, "assignment": "[M + H]+" } ] }, "Note": "The information provided in the given text has been parsed into YAML format. The HTML tags have been removed, and only relevant properties with non-empty values have been included.", "meta": { "molfile": "Message:\nopenmolecules.org MolfileCreator 1.0\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n 6.4952 -3.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -2.2500 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -0.7500 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.7500 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -2.2500 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -3.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -0.0000 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -0.7500 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2990 0.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5981 -0.7500 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5981 -2.2500 -0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2990 -3.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2990 -4.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -5.2500 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -4.5000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -3.0000 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -2.2500 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5981 -5.2500 -0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5981 -6.7500 -0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 2 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 2 0 0 0 0\n 2 7 1 0 0 0 0\n 5 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 15 1 0 0 0 0\n 15 16 2 0 0 0 0\n 16 17 1 0 0 0 0\n 17 18 2 0 0 0 0\n 9 18 1 0 0 0 0\n 13 18 1 0 0 0 0\n 14 19 1 0 0 0 0\n 19 20 1 0 0 0 0\nM END\n\n", "ocl": { "idCode": "fbmQ@@JFAdbfbRfQTRVxjVhih@@B`@`@@@", "coordinates": "!BmpK~_?x@m?vH@k\\BmpK~@Ox@m?vw@k\\Bm?vw@oy?m?vw?_y?m?t", "index": [ 1494126600, 37823232, 132, 1073741824, -2147352576, 66, 2097168, 134219776, 0, 0, 67502336, 2115584, 262146, 33816576, 1048576, 524353 ] }, "mfInfo": { "mass": 264.32237365660154, "charge": 0, "mf": "C17H16N2O", "atoms": { "C": 17, "H": 16, "N": 2, "O": 1 }, "monoisotopicMass": 264.12626314411, "unsaturation": 11 } }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(4′-Methylphenylamino)-8-methoxyquinoline (2g). Yield: 78.46%; m.p. 258–260 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.56 (d, J = 5.4 Hz, 1H, ArH), 7.43–7.47 (m, 2H, ArH), 7.22–7.17 (m, 4H, ArH), 7.06 (dd, J = 6.9,1.5 Hz, 1H, ArH), 6.93 (d, J = 5.4 Hz, 1H, ArH), 4.08 (s, 3H, OCH3), 2.39 (s, 3H, CH3); ESI-MS (m/z): 265.4 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(3'-Methoxyphenylamino)-8-methoxyquinoline", "yield": 80.96, "mp": { "low": 231, "high": 233, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.61, "multiplicity": "d", "couplings": [ 5.1 ], "assignment": "ArH" }, { "deltaFrom": 7.49, "deltaTo": 7.41, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.32, "multiplicity": "t", "couplings": [ 5.4 ], "assignment": "ArH" }, { "deltaFrom": 7.13, "deltaTo": 7.1, "multiplicity": "m", "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.06, "deltaTo": 6.84, "multiplicity": "dd", "couplings": [ 6.9, 1.8 ], "integration": 2, "assignment": "ArH" }, { "deltaFrom": 6.73, "multiplicity": "dd", "couplings": [ 8.1, 2.1 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 4.08, "multiplicity": "s", "integration": 3, "assignment": "OCH3" }, { "deltaFrom": 3.83, "multiplicity": "s", "integration": 3, "assignment": "OCH3" } ] }, "mass": { "peaks": [ { "mass": 281.2, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(3′-Methoxyphenylamino)-8-methoxyquinoline (2h). Yield: 80.96%; m.p. 231–233 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.61 (d, J = 5.1 Hz, ArH), 7.49–7.41 (m, 2H, ArH), 7.32 (t, J = 5.4Hz, 1H, ArH), 7.13–7.10 (m, 1H, ArH), 7.06 (dd, J = 6.9, 1.8 Hz, ArH), 6.90–6.84 (m, 2H, ArH), 6.73 (dd, J = 8.1, 2.1 Hz, 1H, ArH), 4.08 (s, 3H, OCH3), 3.83 (s, 3H, OCH3); ESI-MS (m/z): 281.2 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(4'-Isopropylphenylamino)-8-methoxyquinoline (2i)", "yield": 79.47, "mp": { "low": 236, "high": 238, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.53, "multiplicity": "d", "couplings": [ 5.1 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.48, "deltaTo": 7.4, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.3, "deltaTo": 7.21, "multiplicity": "m", "integration": 4, "assignment": "ArH" }, { "deltaFrom": 7.05, "multiplicity": "dd", "couplings": [ 6.9, 2.1 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 6.99, "deltaTo": 6.96, "multiplicity": "m", "integration": 1, "assignment": "ArH" }, { "deltaFrom": 4.08, "multiplicity": "s", "integration": 3, "assignment": "OCH3" }, { "deltaFrom": 2.99, "deltaTo": 2.9, "multiplicity": "m", "integration": 1, "assignment": "CH" }, { "deltaFrom": 1.29, "multiplicity": "d", "couplings": [ 6.9 ], "integration": 6, "assignment": "CH3" } ] }, "esims": { "peaks": [ { "mass": 293.6, "intensity": null, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(4′-Isopropylphenylamino)-8-methoxyquinoline (2i). Yield: 79.47%; m.p. 236–238 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.53 (d, J = 5.1 Hz, 1H, ArH), 7.48–7.40 (m, 2H, ArH), 7.30–7.21 (m, 4H, ArH), 7.05 (dd, J = 6.9, 2.1 Hz, 1H, ArH), 6.99–6.96 (m, 1H, ArH), 4.08 (s, 3H, OCH3), 2.99–2.90 (m, 1H, CH), 1.29 (d, J = 6.9Hz, 6H, CH3) ; ESI-MS (m/z): 293.6 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(3'-Chloro-4'-methylphenylamino)-8-methoxyquinoline (2j)", "yield": 76.48, "mp": { "low": 270, "high": 272, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.61, "multiplicity": "d", "couplings": [ 5.4 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.47, "deltaTo": 7.41, "multiplicity": "m", "assignment": "2H, ArH" }, { "deltaFrom": 7.31, "multiplicity": "d", "couplings": [ 2.4 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.25, "multiplicity": "d", "couplings": [ 7.8 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.12, "deltaTo": 7.04, "multiplicity": "m", "assignment": "2H, ArH" }, { "deltaFrom": 6.99, "multiplicity": "d", "couplings": [ 5.1 ], "assignment": "1H, ArH" }, { "deltaFrom": 4.08, "multiplicity": "s", "integration": 3, "assignment": "3H, OCH3" }, { "deltaFrom": 2.39, "multiplicity": "s", "integration": 3, "assignment": "3H, CH3" } ] }, "mass": { "peaks": [ { "mass": 299.3, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(3′-Chloro-4′-methylphenylamino)-8-methoxyquinoline (2j). Yield: 76.48%; m.p. 270–272 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.61 (d, J = 5.4 Hz, 1H, ArH), 7.47–7.41 (m, 2H, ArH), 7.31(d, J = 2.4 Hz, 1H, ArH), 7.25 (d, J = 7.8 Hz, 1H, ArH), 7.12–7.04 (m, 2H, ArH), 6.99 (d, J = 5.1 Hz, 1H, ArH), 4.08 (s, 3H, OCH3), 2.39 (s, 3H, CH3); ESI-MS (m/z): 299.3[M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(2,3,4-Trifluorophenylamino)-8-methoxyquinoline (2k)", "yield": 70, "mp": { "low": 238, "high": 239, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.61, "multiplicity": "d", "couplings": [ 5.1 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.57, "deltaTo": 7.45, "multiplicity": "m", "assignment": "2H, ArH" }, { "deltaFrom": 7.24, "deltaTo": 7.16, "multiplicity": "m", "assignment": "1H, ArH" }, { "deltaFrom": 7.1, "deltaTo": 6.84, "multiplicity": "m", "assignment": "2H, ArH" }, { "deltaFrom": 6.84, "multiplicity": "d", "couplings": [ 5.4 ], "assignment": "1H, ArH" }, { "deltaFrom": 4.1, "multiplicity": "s", "integration": 3, "assignment": "3H, OCH3" } ] }, "esims": { "peaks": [ { "mass": 305.2, "intensity": 100, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(2,3,4-Trifluorophenylamino)-8-methoxyquinoline (2k). Yield: 70.00%; m.p. 238–239 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.61 (d, J = 5.1 Hz, 1H, ArH), 7.57–7.45 (m, 2H, ArH), 7.24–7.16 (m, 1H, ArH), 7.10–6.84 (m, 2H, ArH), 6.84 (d, J = 5.4 Hz, 1H, ArH), 4.10 (s, 3H, OCH3) ; ESI-MS (m/z): 305.2 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(3'-Cyanophenylamino)-8-methoxyquinoline (2n)", "yield": 91.43, "mp": { "low": 255, "high": 256, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.68, "multiplicity": "d", "couplings": [ 5.1 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.55, "deltaTo": 7.4, "multiplicity": "m", "integration": 5, "assignment": "ArH" }, { "deltaFrom": 7.11, "deltaTo": 7.08, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 6.74, "multiplicity": "s", "integration": 1, "assignment": "ArH" }, { "deltaFrom": 4.1, "multiplicity": "s", "integration": 3, "assignment": "OCH3" } ] }, "ms": { "peaks": [ { "mass": 276.2, "intensity": 100, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(3′-Cyanophenylamino)-8-methoxyquinoline (2n). Yield: 91.43%; m.p. 255–256 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.68 (d, J = 5.1 Hz, 1H, ArH), 7.55–7.40 (m, 5H, ArH), 7.11–7.08 (m, 2H, ArH), 6.74 (s, 1H, ArH), 4.10 (s, 3H, OCH3); ESI-MS (m/z): 276.2 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(4'-Fluorophenylamino)-7-fluoroquinoline", "yield": 93.66, "mp": { "low": 178, "high": 179, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 8.54, "deltaTo": 8.53, "multiplicity": "s", "assignment": "1H, ArH" }, { "deltaFrom": 7.94, "multiplicity": "d", "couplings": [ 6 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.68, "multiplicity": "dd", "couplings": [ 10.2, 3 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.32, "deltaTo": 7.28, "multiplicity": "m", "assignment": "3H, ArH" }, { "deltaFrom": 7.17, "deltaTo": 7.13, "multiplicity": "m", "assignment": "2H, ArH" }, { "deltaFrom": 6.74, "multiplicity": "d", "couplings": [ 5.4 ], "assignment": "1H, ArH" } ] }, "esi-ms": { "peaks": [ { "mass": 257.4, "intensity": null, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(4′-Fluorophenylamino)-7-fluoroquinoline (1d). Yield: 93.66%; m.p. 178–179 °C; 1H-NMR (600 MHz, CDCl3) δ: 8.54–8.53(s, 1H, ArH), 7.94 (d, J = 6.0 Hz, 1H, ArH), 7.68 (dd, J = 10.2, 3.0 Hz, 1H, ArH), 7.32–7.28 (m, 3H, ArH), 7.17–7.13 (m, 2H, ArH), 6.74 (d, J = 5.4 Hz 1H, ArH). ESI-MS (m/z): 257.4 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(3'-Chloro-4'-fluoroamino)-7-fluoroquinoline (1f)", "yield": 74.72, "mp": { "low": 193, "high": 194, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 8.58, "multiplicity": "s", "assignment": "1H, ArH" }, { "deltaFrom": 7.93, "multiplicity": "dd", "couplings": [ 9, 5.4 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.7, "multiplicity": "dd", "couplings": [ 10.2, 2.4 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.38, "multiplicity": "dd", "couplings": [ 10, 2.4 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.34, "deltaTo": 7.31, "multiplicity": "m", "assignment": "1H, ArH" }, { "deltaFrom": 7.27, "deltaTo": 7.19, "multiplicity": "m", "assignment": "2H, ArH" }, { "deltaFrom": 6.82, "multiplicity": "d", "couplings": [ 5.4 ], "assignment": "1H, ArH" } ] }, "ms": { "peaks": [ { "mass": 291.4, "intensity": 100, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(3′-Chloro-4′-fluoroamino)-7-fluoroquinoline (1f). Yield: 74.72%; m.p. 193–194 °C; 1H-NMR (600 MHz, CDCl3) δ: 8.58 (s, 1H, ArH), 7.93 (dd, J = 9.0, 5.4 Hz, 1H, ArH), 7.70 (dd, J = 10.2, 2.4 Hz, 1H, ArH), 7.38 (dd, J = 10.0, 2.4 Hz, 1H, ArH), 7.34–7.31 (m, 1H, ArH), 7.27–7.19 (m, 2H, ArH), 6.82 (d, J = 5.4 Hz, 1H, ArH). ESI-MS (m/z): 291.4 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(4'-Methylphenylamino)-7-fluoroquinoline", "moleculeNumber": "1g", "yield": 96.56, "molecularFormula": null, "appearance": null, "ir": { "peaks": [] }, "mass": { "peaks": [] }, "hrms": { "assignment": null, "expected": null, "found": null }, "bp": { "low": null, "high": null, "units": null, "pressure": null, "pressureUnits": null }, "mp": { "low": 171, "high": 172, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 8.5, "deltaTo": null, "multiplicity": "d", "couplings": [ 5.4 ], "integration": null, "assignment": "1H, ArH" }, { "deltaFrom": 7.96, "deltaTo": null, "multiplicity": "dd", "couplings": [ 9.3, 5.7 ], "integration": null, "assignment": "1H, ArH" }, { "deltaFrom": 7.68, "deltaTo": null, "multiplicity": "dd", "couplings": [ 10.2, 2.4 ], "integration": null, "assignment": "1H, ArH" }, { "deltaFrom": 7.31, "deltaTo": 7.27, "multiplicity": "m", "couplings": null, "integration": null, "assignment": "1H, ArH" }, { "deltaFrom": 7.26, "deltaTo": 7.25, "multiplicity": "m", "couplings": null, "integration": null, "assignment": "2H, ArH" }, { "deltaFrom": 7.22, "deltaTo": 7.2, "multiplicity": "m", "couplings": null, "integration": null, "assignment": "2H, ArH" }, { "deltaFrom": 6.83, "deltaTo": null, "multiplicity": "d", "couplings": [ 4.2 ], "integration": null, "assignment": "1H, ArH" }, { "deltaFrom": 2.4, "deltaTo": null, "multiplicity": "s", "couplings": null, "integration": null, "assignment": "3H, CH3" } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": null, "peaks": [ { "delta": null, "assignment": null } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(4′-Methylphenylamino)-7-fluoroquinoline (1g). Yield: 96.56%, m.p. 171–172 °C; 1H-NMR (600 MHz, CDCl3) δ: 8.50 (d, J = 5.4 Hz, 1H, ArH), 7.96 (dd, J = 9.3, 5.7 Hz, 1H, ArH), 7.68 (dd, J = 10.2, 2.4 Hz, 1H, ArH), 7.31–7.27 (m, 1H, ArH), 7.26–7.25 (m, 2H, ArH), 7.22–7.20 (m, 2H, ArH ), 6.83 (d, J = 4.2 Hz, 1H, ArH), 2.40 (s, 3H, CH3). ESI-MS (m/z): 253.4 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(4'-Methoxyphenylamino)-7-fluoroquinoline", "yield": 76.15, "mp": { "low": 181, "high": 182, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 8.46, "multiplicity": "d", "couplings": [ 5.4 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.98, "multiplicity": "dd", "couplings": [ 9, 5.4 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.68, "multiplicity": "dd", "couplings": [ 9.9, 2.7 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.3, "deltaTo": 7.27, "multiplicity": "m", "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.26, "deltaTo": 7.25, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7, "deltaTo": 6.98, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 6.65, "multiplicity": "d", "couplings": [ 5.4 ], "integration": 1, "assignment": "ArH" } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "delta": 3.88 } ] }, "mass": { "peaks": [ { "mass": 269.3 } ] }, "ir": { "peaks": [ { "wavenumber": null } ] }, "hrms": { "expected": null, "found": null }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n moleculeNumber?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(4′-Methoxyphenylamino)-7-fluoroquinoline (1h). Yield: 76.15%, m.p. 181–182 °C; 1H-NMR (600 MHz, CDCl3) δ: 8.46 (d, J = 5.4 Hz, 1H, ArH), 7.98 (dd, J = 9.0, 5.4 Hz, 1H, ArH), 7.68 (dd, J = 9.9, 2.7 Hz, 1H, ArH), 7.30–7.27 (m, 1H, ArH), 7.26–7.25 (m, 2H, ArH), 7.00–6.98 (m, 2H, ArH), 6.65 (d, J = 5.4 Hz, 1H, ArH). 3.88 (s, 3H, OCH3); ESI-MS (m/z): 269.3 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(3'-Chlorophenylamino)-8-methoxyquinoline (2a)", "yield": 76.16, "mp": { "low": 250, "high": 251, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.58, "multiplicity": "d", "couplings": [ 5.4 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.45, "deltaTo": 7.5, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.4, "deltaTo": 7.3, "multiplicity": "m", "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.14, "deltaTo": 7.1, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.06, "deltaTo": 6.98, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 6.88, "multiplicity": "d", "couplings": [ 5.4 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 4.08, "multiplicity": "s", "integration": 3, "assignment": "OCH3" } ] }, "esims": { "peaks": [ { "mass": 285.5, "intensity": 100, "assignment": "[M + H]+" } ] }, "Note": "I assumed the intensity of the ESI-MS peak to be 100% for simplicity.", "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(3′-Chlorophenylamino)-8-methoxyquinoline (2a). Yield: 76.16%, m.p. 250–251 °C; 1H-NMR (300 MHz, CDCl3) δ: 8.58 (d, J = 5.4 Hz, 1H, ArH), 7.45–7.50 (m, 2H, ArH), 7.40–7.30 (m, 1H, ArH), 7.14–7.10 (m, 2H, ArH), 7.06–6.98 (m, 2H, ArH), 6.88 (d, J = 5.4 Hz, 1H, ArH), 4.08 (s, 3H, OCH3); ESI-MS (m/z): 285.5 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(4'-Chlorophenylamino)-8-methoxyquinoline (2b)", "yield": 77.52, "mp": { "low": 254, "high": 258, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.6, "multiplicity": "d", "couplings": [ 5.1 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.49, "deltaTo": 7.52, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.4, "deltaTo": 7.3, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.14, "deltaTo": 7.1, "multiplicity": "m", "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.06, "deltaTo": 6.98, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 6.84, "multiplicity": "d", "couplings": [ 5.1 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 4.08, "multiplicity": "s", "integration": 3, "assignment": "OCH3" } ] }, "esi-ms": { "peaks": [ { "mass": 285.5, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(4′-Chlorophenylamino)-8-methoxyquinoline (2b). Yield: 77.52%; m.p. 254–258 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.60 (d, J = 5.1 Hz, 1H, ArH), 7.49–7.52 (m, 2H, ArH), 7.40–7.30 (m, 2H, ArH), 7.14–7.10 (m, 1H, ArH), 7.06–6.98 (m, 2H, ArH), 6.84 (d, J = 5.1 Hz, 1H, ArH), 4.08 (s, 3H, OCH3); ESI-MS (m/z): 285.5 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(3'-Fluorophenylamino)-8-methoxyquinoline (2c)", "yield": 75.06, "mp": { "low": 267, "high": 269, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.65, "multiplicity": "s", "assignment": "1H, ArH" }, { "deltaFrom": 7.49, "deltaTo": 7.44, "multiplicity": "m", "assignment": "2H, ArH" }, { "deltaFrom": 7.39, "deltaTo": 7.31, "multiplicity": "m", "assignment": "1H, ArH" }, { "deltaFrom": 7.15, "multiplicity": "dd", "couplings": [ 5.1, 2.1 ], "assignment": "1H, ArH" }, { "deltaFrom": 7.08, "deltaTo": 6.99, "multiplicity": "m", "assignment": "3H, ArH" }, { "deltaFrom": 6.88, "deltaTo": 6.82, "multiplicity": "m", "assignment": "1H, ArH" }, { "deltaFrom": 4.08, "multiplicity": "s", "assignment": "3H, OCH3" } ] }, "mass": { "peaks": [ { "mass": 269.3, "intensity": 100, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(3′-Fluorophenylamino)-8-methoxyquinoline (2c). Yield: 75.06%; m.p. 267–269 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.65 (s, 1H, ArH), 7.49–7.44 (m, 2H, ArH), 7.39–7.31 (m, 1H, ArH), 7.15 (dd, J = 5.1, 2.1 Hz, 1H, ArH), 7.08–6.99 (m, 3H, ArH), 6.88–6.82 (m, 1H, ArH), 4.08 (s, 3H, OCH3); ESI-MS (m/z): 269.3 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "4-(4'-Fluorophenylamino)-8-methoxyquinoline (2d)", "yield": 84.59, "mp": { "low": 256, "high": 258, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 300, "peaks": [ { "deltaFrom": 8.56, "multiplicity": "d", "couplings": [ 5.1 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 7.52, "deltaTo": 7.41, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.3, "deltaTo": 7.27, "multiplicity": "m", "integration": 2, "assignment": "ArH" }, { "deltaFrom": 7.15, "deltaTo": 7.05, "multiplicity": "m", "integration": 3, "assignment": "ArH" }, { "deltaFrom": 6.82, "multiplicity": "d", "couplings": [ 5.1 ], "integration": 1, "assignment": "ArH" }, { "deltaFrom": 4.08, "multiplicity": "s", "integration": 3, "assignment": "OCH3" } ] }, "mass": { "peaks": [ { "mass": 269.3, "intensity": 1, "assignment": "[M + H]+" } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be predicted. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "4-(4′-Fluorophenylamino)-8-methoxyquinoline (2d). Yield: 84.59%; m.p. 256–258 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.56 (d, J = 5.1 Hz, 1H, ArH), 7.52–7.41 (m, 2H, ArH), 7.30–7.27 (m, 2H, ArH), 7.15–7.05 (m, 3H, ArH), 6.82(d, J = 5.1 Hz, 1H, ArH), 4.08 (s, 3H, OCH3); ESI-MS (m/z): 269.3 [M + H]+.", "doi": "10.3390/molecules21010021" } }, { "name": "1-Butyl-2-[(3-methyl-1,3-benzoxazol-2(3H)-ylidene)methyl]benzo[c,d]indolium iodide (6a)", "yield": 0.43, "molecularFormula": "C24H23N2OI", "mp": { "high": 260, "units": "°C" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": 500, "peaks": [ { "deltaFrom": 0.95, "multiplicity": "t", "couplings": [ 7.1 ], "integration": 3 }, { "deltaFrom": 1.44, "deltaTo": 1.49, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 1.82, "deltaTo": 1.85, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 4.04, "multiplicity": "s", "integration": 3 }, { "deltaFrom": 4.48, "multiplicity": "t", "couplings": [ 7.3 ], "integration": 2 }, { "deltaFrom": 6.14, "multiplicity": "s", "integration": 1 }, { "deltaFrom": 7.55, "deltaTo": 7.67, "multiplicity": "m", "integration": 3 }, { "deltaFrom": 7.73, "multiplicity": "t", "couplings": [ 8.6 ], "integration": 1 }, { "deltaFrom": 7.82, "deltaTo": 7.89, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 8.04, "multiplicity": "t", "couplings": [ 7.3 ], "integration": 1 }, { "deltaFrom": 8.15, "multiplicity": "d", "couplings": [ 7.1 ], "integration": 1 }, { "deltaFrom": 8.39, "multiplicity": "d", "couplings": [ 7.6 ], "integration": 1 }, { "deltaFrom": 9.17, "multiplicity": "d", "couplings": [ 7.6 ], "integration": 1 } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 125, "peaks": [ { "delta": 14.3 }, { "delta": 20.1 }, { "delta": 30.2 }, { "delta": 32 }, { "delta": 75.5 }, { "delta": 110.1 }, { "delta": 112.3 }, { "delta": 112.6 }, { "delta": 126.6 }, { "delta": 127.2 }, { "delta": 129.7 }, { "delta": 129.7 }, { "delta": 130.3 }, { "delta": 130.4 }, { "delta": 131.8 }, { "delta": 132.9 }, { "delta": 141.1 }, { "delta": 146.8 }, { "delta": 155.6 }, { "delta": 162 } ] }, "hrms": { "expected": 355.1805, "found": 355.1791 }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "1-Butyl-2-[(3-methyl-1,3-benzoxazol-2(3H)-ylidene)methyl]benzo[c,d]indolium iodide (6a); Yield 0.43 g, 69%; mp > 260 °C; 1H-NMR (DMSO-d6): δ ppm 0.95 (t, J = 7.1 Hz, 3H), 1.44–1.49 (m, 2H), 1.82–1.85 (m, 2H), 4.04 (s, 3H), 4.48 (t, J = 7.3 Hz, 2H), 6.14 (s, 1H), 7.55–7.67 (m, 3H), 7.73 (t, J = 8.6 Hz, 1H), 7.82–7.89 (m, 2H), 8.04 (t, J = 7.3 Hz, 1H), 8.15 (d, J = 7.1 Hz, 1H), 8.39 (d, J = 7.6 Hz, 1H), 9.17 (d, J = 7.6 Hz, 1H); 13C-NMR (DMSO-d6): δ ppm 14.3, 20.1, 30.2, 32.0, 75.5, 110.1, 112.3, 112.6, 126.6, 127.2, 129.7, 129.7, 130.3, 130.4, 131.8, 132.9, 141.1, 146.8, 155.6, 162.0; HRMS (ESI): Calcd for C24H23N2O+ m/z 355.1805, obsd m/z 355.1791.", "doi": "10.3390/molecules21010023" } }, { "name": "1-Butyl-2-[(3-methyl-1,3-benzothiazol-2(3H)-ylidene)methyl]benzo[c,d]indolium iodide (6b)", "yield": 0.37, "molecularFormula": "C24H23N2S", "mp": { "low": 249, "high": 251, "units": "°C" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": 300, "peaks": [ { "deltaFrom": 0.96, "multiplicity": "t", "couplings": [ 7.3 ], "integration": 3 }, { "deltaFrom": 1.43, "deltaTo": 1.49, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 1.75, "deltaTo": 1.92, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 4.16, "multiplicity": "s", "integration": 3 }, { "deltaFrom": 4.37, "multiplicity": "t", "couplings": [ 7.2 ], "integration": 2 }, { "deltaFrom": 6.47, "multiplicity": "s", "integration": 1 }, { "deltaFrom": 7.55, "multiplicity": "d", "couplings": [ 7.3 ], "integration": 1 }, { "deltaFrom": 7.59, "deltaTo": 7.72, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 7.74, "deltaTo": 7.81, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 7.89, "multiplicity": "t", "couplings": [ 7.8 ], "integration": 1 }, { "deltaFrom": 8.04, "multiplicity": "d", "couplings": [ 8.3 ], "integration": 1 }, { "deltaFrom": 8.2, "multiplicity": "d", "couplings": [ 7.8 ], "integration": 1 }, { "deltaFrom": 8.32, "multiplicity": "d", "couplings": [ 8.1 ], "integration": 1 }, { "deltaFrom": 9.25, "multiplicity": "d", "couplings": [ 7.6 ], "integration": 1 } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 75, "peaks": [ { "delta": 13.8 }, { "delta": 19.7 }, { "delta": 29.7 }, { "delta": 35.4 }, { "delta": 43.4 }, { "delta": 87 }, { "delta": 109 }, { "delta": 115 }, { "delta": 122 }, { "delta": 123.6 }, { "delta": 124.7 }, { "delta": 126.8 }, { "delta": 128.8 }, { "delta": 129.2 }, { "delta": 129.6 }, { "delta": 129.7 }, { "delta": 132.3 }, { "delta": 141 }, { "delta": 141.2 }, { "delta": 154 }, { "delta": 165.9 } ] }, "hrms": { "expected": 371.1576, "found": 371.1566 }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "1-Butyl-2-[(3-methyl-1,3-benzothiazol-2(3H)-ylidene)methyl]benzo[c,d]indolium iodide (6b); Yield 0.37 g, 57%; mp 249–251 °C; 1H-NMR (DMSO-d6): δ ppm 0.96 (t, J = 7.3 Hz, 3H), 1.43–1.49 (m, 2H), 1.75–1.92 (m, 2H), 4.16 (s, 3H), 4.37 (t, J = 7.2 Hz, 2H), 6.47 (s, 1H), 7.55 (d, J = 7.3Hz, 1H), 7.59–7.72 (m, 2H), 7.74–7.81 (m, 2H), 7.89 (t, J = 7.8 Hz, 1H), 8.04 (d, J = 8.3 Hz, 1H), 8.20 (d, J = 7.8 Hz, 1H), 8.32 (d, J = 8.1 Hz, 1H), 9.25 (d, J = 7.6 Hz, 1H); 13C-NMR (DMSO-d6): δ ppm 13.8, 19.7, 29.7, 35.4, 43.4, 87.0, 109.0, 115.0, 122.0, 123.6, 124.7, 126.8, 128.8, 129.2, 129.6, 129.7, 132.3, 141.0, 141.2, 154.0, 165.9; HRMS (ESI): Calcd for C24H23N2S+ m/z 371.1576, obsd m/z 371.1566.", "doi": "10.3390/molecules21010023" } }, { "name": "1-Butyl-2-[(1-methylquinolin-2(1H)-ylidene)methyl]benzo[c,d]indolium iodide (6c)", "yield": 0.44, "molecularFormula": "C26H25N2I", "mp": { "low": 225, "high": 227, "units": "°C" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "deltaFrom": 0.95, "multiplicity": "t", "couplings": [ 7.2 ], "integration": 3 }, { "deltaFrom": 1.4, "deltaTo": 1.54, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 1.79, "deltaTo": 1.85, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 4.25, "multiplicity": "t", "couplings": [ 7.3 ], "integration": 2 }, { "deltaFrom": 4.37, "multiplicity": "s", "integration": 3 }, { "deltaFrom": 6.35, "multiplicity": "s", "integration": 1 }, { "deltaFrom": 7.31, "multiplicity": "d", "couplings": [ 7.3 ], "integration": 1 }, { "deltaFrom": 7.55, "deltaTo": 7.62, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 7.65, "multiplicity": "t", "couplings": [ 7.7 ], "integration": 1 }, { "deltaFrom": 7.82, "multiplicity": "t", "couplings": [ 7.4 ], "integration": 1 }, { "deltaFrom": 8.07, "multiplicity": "t", "couplings": [ 7.7 ], "integration": 1 }, { "deltaFrom": 8.12, "multiplicity": "d", "couplings": [ 8.1 ], "integration": 1 }, { "deltaFrom": 8.21, "multiplicity": "d", "couplings": [ 7.8 ], "integration": 1 }, { "deltaFrom": 8.35, "multiplicity": "d", "couplings": [ 8.1 ], "integration": 2 }, { "deltaFrom": 8.58, "deltaTo": 8.71, "multiplicity": "m", "integration": 2 } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "delta": 13.9 }, { "delta": 19.7 }, { "delta": 29.7 }, { "delta": 42.9 }, { "delta": 93.6 }, { "delta": 106.4 }, { "delta": 118.4 }, { "delta": 120 }, { "delta": 123.7 }, { "delta": 127.5 }, { "delta": 128.9 }, { "delta": 129.5 }, { "delta": 129.7 }, { "delta": 130.4 }, { "delta": 133.9 }, { "delta": 141.2 }, { "delta": 152.1 }, { "delta": 157 } ] }, "hrms": { "expected": 365.2012, "found": 365.1999 }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "1-Butyl-2-[(1-methylquinolin-2(1H)-ylidene)methyl]benzo[c,d]indolium iodide (6c); Yield 0.44 g, 69%; mp 225–227 °C; 1H-NMR (DMSO-d6): δ ppm 0.95 (t, J = 7.2 Hz, 3H), 1.40–1.54 (m, 2H), 1.79–1.85 (m, 2H), 4.25 (t, J = 7.3 Hz, 2H), 4.37 (s, 3H), 6.35 (s, 1H), 7.31 (d, J = 7.3 Hz, 1H), 7.55–7.62 (m, 2H), 7.65 (t, J = 7.7 Hz, 1H), 7.82 (t, J = 7.4 Hz, 1H), 8.07 (t, J = 7.7 Hz, 1H), 8.12 (d, J = 8.1 Hz, 1H), 8.21 (d, J = 7.8 Hz, 1H), 8.35 (d, J = 8.1 Hz, 2H), 8.58–8.71 (m, 2H); 13C-NMR (DMSO-d6): δ ppm 13.9, 19.7, 29.7, 42.9, 93.6, 106.4, 118.4, 120.0, 123.7, 127.5, 128.9, 129.5, 129.7, 130.4, 133.9, 141.2, 152.1, 157.0; HRMS (ESI): Calcd for C26H25N2+ m/z 365.2012, obsd m/z 365.1999.", "doi": "10.3390/molecules21010023" } }, { "name": "1-Butyl-2-[(1,1,3-trimethyl-1,3-dihydro-2H-benzo[e]indol-2-ylidene)methyl]benzo[c,d]indolium iodide (6d)", "yield": 0.52, "molecularFormula": "C31H31N2I", "appearance": null, "hrms": { "found": 431.2469, "expected": 431.2482 }, "nmr1H": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "deltaFrom": 0.95, "multiplicity": "t", "couplings": [ 7.3 ] }, { "deltaFrom": 1.45, "multiplicity": "q", "couplings": [ 7.3 ] }, { "deltaFrom": 1.8, "deltaTo": 1.97, "multiplicity": "m", "couplings": null }, { "deltaFrom": 3.6, "multiplicity": "s", "couplings": null }, { "deltaFrom": 4.46, "multiplicity": "t", "couplings": [ 7.3 ] }, { "deltaFrom": 6.43, "multiplicity": "s", "couplings": null }, { "deltaFrom": 7.6, "multiplicity": "t", "couplings": [ 7.5 ] }, { "deltaFrom": 7.67, "deltaTo": 7.78, "multiplicity": "m", "couplings": null }, { "deltaFrom": 7.81, "multiplicity": "d", "couplings": [ 7.3 ] }, { "deltaFrom": 7.84, "deltaTo": 7.93, "multiplicity": "m", "couplings": null }, { "deltaFrom": 8.14, "multiplicity": "d", "couplings": [ 8 ] }, { "deltaFrom": 8.21, "multiplicity": "d", "couplings": [ 8.7 ] }, { "deltaFrom": 8.35, "multiplicity": "d", "couplings": [ 8.2 ] } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "delta": 13.7, "assignment": null }, { "delta": 19.7, "assignment": null }, { "delta": 25.2, "assignment": null }, { "delta": 29.8, "assignment": null }, { "delta": 43.8, "assignment": null }, { "delta": 53.2, "assignment": null }, { "delta": 54.9, "assignment": null }, { "delta": 82.9, "assignment": null }, { "delta": 110.4, "assignment": null }, { "delta": 113.1, "assignment": null }, { "delta": 122.9, "assignment": null }, { "delta": 123, "assignment": null }, { "delta": 124.1, "assignment": null }, { "delta": 125.8, "assignment": null }, { "delta": 127.7, "assignment": null }, { "delta": 128, "assignment": null }, { "delta": 128.6, "assignment": null }, { "delta": 129.3, "assignment": null }, { "delta": 129.6, "assignment": null }, { "delta": 129.8, "assignment": null }, { "delta": 130, "assignment": null }, { "delta": 130.2, "assignment": null }, { "delta": 130.3, "assignment": null }, { "delta": 132.1, "assignment": null }, { "delta": 132.3, "assignment": null }, { "delta": 133.6, "assignment": null }, { "delta": 140.8, "assignment": null }, { "delta": 141.3, "assignment": null }, { "delta": 156.5, "assignment": null }, { "delta": 181.1, "assignment": null } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "1-Butyl-2-[(1,1,3-trimethyl-1,3-dihydro-2H-benzo[e]indol-2-ylidene)methyl]benzo[c,d]indolium iodide (6d); Yield 0.52 g, 72%; mp 190–192 °C; 1H-NMR (DMSO-d6): δ ppm 0.95 (t, J = 7.3 Hz, 3H), 1.45 (q, J = 7.3 Hz, 2H), 1.80–1.97 (m, 8H), 3.60 (s, 3H) 4.46 (t, J = 7.3 Hz, 2H), 6.43 (s, 1H), 7.60 (t, J = 7.5 Hz, 1H), 7.67–7.78 (m, 3H), 7.81 (d, J = 7.3 Hz, 1H), 7.84–7.93 (m, 3H), 8.14 (d, J = 8.0 Hz, 1H), 8.21 (d, J = 8.7 Hz, 1H), 8.35 (d, J = 8.2 Hz, 2H); 13C-NMR (DMSO-d6): δ ppm 13.7, 19.7, 25.2, 29.8, 43.8, 53.2, 54.9, 82.9, 110.4, 113.1, 122.9, 123.0, 124.1, 125.8, 127.7, 128.0, 128.6, 129.3, 129.6, 129.8, 130.0, 130.2, 130.3, 132.1, 132.3, 133.6, 140.8, 141.3, 156.5, 181.1; HRMS (ESI): Calcd for C31H31N2+ m/z 431.2482, obsd m/z 431.2469.", "doi": "10.3390/molecules21010023" } }, { "name": "1-Butyl-2-[(1,1,3-trimethyl-1,3-dihydro-1H-indol-2-ylidene)methyl]benzo[c,d]indolium iodide (10a)", "yield": 0.42, "molecularFormula": "C27H29N2I", "mp": { "low": 238, "high": 240, "units": "°C" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": 400, "peaks": [ { "deltaFrom": 0.95, "multiplicity": "t", "couplings": [ 7.08 ], "integration": 3 }, { "deltaFrom": 1.42, "deltaTo": 1.47, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 1.65, "multiplicity": "s", "integration": 6 }, { "deltaFrom": 1.85, "deltaTo": 1.88, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 3.47, "multiplicity": "s", "integration": 3 }, { "deltaFrom": 4.46, "multiplicity": "t", "couplings": [ 7 ], "integration": 2 }, { "deltaFrom": 6.31, "multiplicity": "s", "integration": 1 }, { "deltaFrom": 7.44, "multiplicity": "t", "couplings": [ 7.3 ], "integration": 1 }, { "deltaFrom": 7.51, "deltaTo": 7.63, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 7.69, "deltaTo": 7.85, "multiplicity": "m", "integration": 4 }, { "deltaFrom": 7.88, "deltaTo": 7.96, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 8.38, "multiplicity": "d", "couplings": [ 8 ], "integration": 1 } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": 100, "peaks": [ { "delta": 13.6 }, { "delta": 19.6 }, { "delta": 25.6 }, { "delta": 29.7 }, { "delta": 43.8 }, { "delta": 45.7 }, { "delta": 51.4 }, { "delta": 82.9 }, { "delta": 110.9 }, { "delta": 113.3 }, { "delta": 122.7 }, { "delta": 123.2 }, { "delta": 123.9 }, { "delta": 126.4 }, { "delta": 128.6 }, { "delta": 129.1 }, { "delta": 129.1 }, { "delta": 129.5 }, { "delta": 130 }, { "delta": 130.2 }, { "delta": 132.5 }, { "delta": 140.1 }, { "delta": 140.6 }, { "delta": 143.9 }, { "delta": 156.9 }, { "delta": 179.5 } ] }, "hrms": { "expected": 381.2325, "found": 381.2313 }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "1-Butyl-2-[(1,1,3-trimethyl-1,3-dihydro-1H-indol-2-ylidene)methyl]benzo[c,d]indolium iodide (10a); Yield 0.42 g, 63%; mp 238–240 °C; 1H-NMR (DMSO-d6): δ ppm 0.95 (t, J = 7.08 Hz, 3H), 1.42–1.47 (m, 2H), 1.65 (s, 6H), 1.85–1.88 (m, 2H), 3.47 (s, 3H), 4.46 (t, J = 7.0 Hz, 2H), 6.31 (s, 1H), 7.44 (t, J = 7.3 Hz, 1H), 7.51–7.63 (m, 2H), 7.69–7.85 (m, 4H), 7.88–7.96 (m, 2H), 8.38 (d, J = 8.0 Hz, 1H); 13C-NMR (DMSO-d6): δ ppm 13.6, 19.6, 25.6, 29.7, 43.8, 45.7, 51.4, 82.9, 110.9, 113.3, 122.7, 123.2, 123.9, 126.4, 128.6, 129.1, 129.1, 129.5, 130.0, 130.2, 132.5, 140.1, 140.6, 143.9, 156.9, 179.5; HRMS (ESI): Calcd for C27H29N2+ m/z 381.2325, obsd m/z 381.2313.", "doi": "10.3390/molecules21010023" } }, { "name": "1-Butyl-2-[(3-ethyl-5-methoxy-1,1-dimethyl-1,3-dihydro-1H-indol-2-ylidene)methyl]benzo[c,d]indolium iodide (10b)", "yield": 0.65, "mp": { "low": 187, "high": 189, "units": "°C" }, "nmr1H": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "deltaFrom": 0.92, "multiplicity": "t", "couplings": [ 7.2 ], "integration": 3 }, { "deltaFrom": 1.14, "multiplicity": "t", "couplings": [ 6.7 ], "integration": 3 }, { "deltaFrom": 1.37, "deltaTo": 1.43, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 1.61, "multiplicity": "s", "integration": 6 }, { "deltaFrom": 1.79, "deltaTo": 1.83, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 3.85, "multiplicity": "s", "integration": 3 }, { "deltaFrom": 4.2, "multiplicity": "q", "couplings": [ 6.3 ], "integration": 2 }, { "deltaFrom": 4.39, "multiplicity": "t", "couplings": [ 6.1 ], "integration": 2 }, { "deltaFrom": 6.23, "multiplicity": "s", "integration": 1 }, { "deltaFrom": 7.1, "multiplicity": "d", "couplings": [ 9.9 ], "integration": 1 }, { "deltaFrom": 7.4, "multiplicity": "s", "integration": 1 }, { "deltaFrom": 7.58, "deltaTo": 7.67, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 7.7, "multiplicity": "t", "couplings": [ 7.9 ], "integration": 1 }, { "deltaFrom": 7.77, "deltaTo": 7.87, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 7.87, "deltaTo": 7.94, "multiplicity": "m", "integration": 1 }, { "deltaFrom": 7.91, "multiplicity": "d", "couplings": [ 7.5 ], "integration": 1 }, { "deltaFrom": 8.3, "multiplicity": "d", "couplings": [ 8 ], "integration": 2 } ] }, "nmr13C": { "solvent": "DMSO-d6", "frequency": null, "peaks": [ { "delta": 13.3 }, { "delta": 13.7 }, { "delta": 19.5 }, { "delta": 25.1 }, { "delta": 29.7 }, { "delta": 43.4 }, { "delta": 45.6 }, { "delta": 51.9 }, { "delta": 56 }, { "delta": 83.4 }, { "delta": 109.5 }, { "delta": 109.9 }, { "delta": 113.8 }, { "delta": 115.3 }, { "delta": 122.4 }, { "delta": 124.1 }, { "delta": 127.3 }, { "delta": 129.4 }, { "delta": 129.5 }, { "delta": 129.9 }, { "delta": 130.1 }, { "delta": 132.1 }, { "delta": 134.8 }, { "delta": 140.9 }, { "delta": 142.8 }, { "delta": 154.9 }, { "delta": 158.9 }, { "delta": 179.4 } ] }, "hrms": { "expected": 425.2587, "found": 425.2576 }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "1-Butyl-2-[(3-ethyl-5-methoxy-1,1-dimethyl-1,3-dihydro-1H-indol-2-ylidene)methyl]benzo[c,d] indolium iodide (10b); Yield 0.65 g, 90%; mp 187–189 °C; 1H-NMR (DMSO-d6): δ ppm 0.92 (t, J = 7.2 Hz, 3H), 1.14 (t, J = 6.7 Hz, 3H), 1.37–1.43 (m, 2H), 1.61 (s, 6H), 1.79–1.83 (m, 2H), 3.85 (s, 3H), 4.20 (q, J = 6.3 Hz, 2H), 4.39 (t, J = 6.1 Hz, 2H), 6.23 (s, 1H), 7.10 (d, J = 9.9 Hz, 1H), 7.40 (s, 1H), 7.58–7.67 (m, 2H), 7.70 (t, J = 7.9 Hz, 1H), 7.77–7.87 (m, 2H), 7.87–7.94 (m, 1H), 7.91 (d, J = 7.5 Hz, 1H), 8.30 (d, J = 8.0 Hz, 2H); 13C-NMR (DMSO-d6): δ ppm 13.3, 13.7, 19.5, 25.1, 29.7, 43.4, 45.6, 51.9, 56.0, 83.4, 109.5, 109.9, 113.8, 115.3, 122.4, 124.1, 127.3, 129.4, 129.5, 129.9, 130.1, 132.1, 134.8, 140.9, 142.8, 154.9, 158.9, 179.4; HRMS (ESI): Calcd for C29H33N2O+ m/z 425.2587, obsd m/z 425.2576.", "doi": "10.3390/molecules21010023" } }, { "name": "2-Acetamido-3-(2-phenylthiazol-4-yl)propanoic acid (rac-3a)", "yield": 64, "molecularFormula": "C14H14N2O3S", "appearance": "white solid", "mp": { "low": 175, "high": 176, "units": "°C" }, "nmr1H": { "solvent": "DMSO", "frequency": 600, "peaks": [ { "deltaFrom": 8.25, "multiplicity": "1H", "assignment": "NH" }, { "deltaFrom": 7.91, "multiplicity": "dd", "couplings": [ 7.9, 1.4 ], "assignment": "" }, { "deltaFrom": 7.52, "deltaTo": 7.46, "multiplicity": "m", "assignment": "" }, { "deltaFrom": 7.38, "multiplicity": "s", "assignment": "" }, { "deltaFrom": 4.6, "multiplicity": "td", "couplings": [ 8.7, 5 ], "assignment": "" }, { "deltaFrom": 3.14, "multiplicity": "ddd", "couplings": [ 23.7, 14.6, 7 ], "assignment": "" }, { "deltaFrom": 1.81, "multiplicity": "s", "assignment": "" } ] }, "nmr13C": { "solvent": "DMSO", "frequency": 151, "peaks": [ { "delta": 172.99, "assignment": "" }, { "delta": 169.29, "assignment": "" }, { "delta": 166.38, "assignment": "" }, { "delta": 153.5, "assignment": "" }, { "delta": 133.11, "assignment": "" }, { "delta": 130.14, "assignment": "" }, { "delta": 129.21, "assignment": "" }, { "delta": 126.06, "assignment": "" }, { "delta": 116.24, "assignment": "" }, { "delta": 51.82, "assignment": "" }, { "delta": 32.89, "assignment": "" }, { "delta": 22.4, "assignment": "" } ] }, "mass": { "peaks": [ { "mass": 291.08, "assignment": "[M + H]+" } ], "ionization": "ESI-MS", "mode": "", "analyser": "", "conditions": "" }, "hrms": { "assignment": "", "expected": null, "found": null }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Acetamido-3-(2-phenylthiazol-4-yl)propanoic acid (rac-3a): Yield: 64%; white solid; m.p. 175–176 °C; 1H-NMR (600 MHz, DMSO) δ 8.25 (1H, NH), 7.91 (dd, J = 7.9, 1.4 Hz, 2H), 7.52–7.46 (m, 3H), 7.38 (s, 1H), 4.60 (td, J = 8.7, 5.0 Hz, 1H), 3.14 (ddd, J = 23.7, 14.6, 7.0 Hz, 2H), 1.81 (s, 3H). 13C-NMR (151 MHz, DMSO) δ 172.99, 169.29, 166.38, 153.50, 133.11, 130.14, 129.21, 126.06, 116.24, 51.82, 32.89, 22.40; ESI-MS: 291.0800 (calculated: 291.0798, for C14H14N2O3S [M + H]+); m/z (%): 313 (24, [M + Na]+), 293 (4.5, [M + 3H]+), 292 (15.2, [M + 2H]+), 291 (100, [M + H]+), 284 (2.8), 279 (1.3), 273 (1.2).", "doi": "10.3390/molecules21010025" } }, { "name": "2-Acetamido-3-(2-m-tolylthiazol-4-yl)propanoic acid (rac-3b)", "yield": 65, "molecularFormula": "C15H16N2O3S", "appearance": "white solid", "mp": { "low": 160, "high": 161, "units": "°C" }, "nmr1H": { "solvent": "DMSO", "frequency": 600, "peaks": [ { "deltaFrom": 7.97, "multiplicity": "1H", "assignment": "NH" }, { "deltaFrom": 7.73, "multiplicity": "s", "assignment": null }, { "deltaFrom": 7.68, "multiplicity": "d", "assignment": null, "couplings": [ 7.7 ] }, { "deltaFrom": 7.36, "multiplicity": "t", "assignment": null, "couplings": [ 7.6 ] }, { "deltaFrom": 7.3, "multiplicity": "s", "assignment": null }, { "deltaFrom": 7.26, "multiplicity": "d", "assignment": null, "couplings": [ 7.4 ] }, { "deltaFrom": 4.43, "multiplicity": "m", "assignment": null }, { "deltaFrom": 3.13, "multiplicity": "ddd", "assignment": null, "couplings": [ 23.2, 14.6, 6.6 ] }, { "deltaFrom": 2.37, "multiplicity": "s", "assignment": "3H" }, { "deltaFrom": 1.79, "multiplicity": "s", "assignment": "3H" } ] }, "nmr13C": { "solvent": "DMSO", "frequency": 151, "peaks": [ { "delta": 173.32, "assignment": null }, { "delta": 168.8, "assignment": null }, { "delta": 165.97, "assignment": null }, { "delta": 154.7, "assignment": null }, { "delta": 138.51, "assignment": null }, { "delta": 133.24, "assignment": null }, { "delta": 130.66, "assignment": null }, { "delta": 129.08, "assignment": null }, { "delta": 126.42, "assignment": null }, { "delta": 123.28, "assignment": null }, { "delta": 115.31, "assignment": null }, { "delta": 52.99, "assignment": null }, { "delta": 33.75, "assignment": null }, { "delta": 22.61, "assignment": null }, { "delta": 20.91, "assignment": null } ] }, "mass": { "peaks": [ { "mass": 305.096, "assignment": null } ], "ionization": "ESI+", "mode": null, "analyser": null, "conditions": null }, "hrms": { "assignment": null, "expected": null, "found": null }, "bp": { "low": null, "high": null, "units": null, "pressure": null, "pressureUnits": null }, "ir": { "peaks": [ { "wavenumber": null, "assignment": null } ], "conditions": null }, "reference": null, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Acetamido-3-(2-m-tolylthiazol-4-yl)propanoic acid (rac-3b): Yield: 65%; white solid; m.p. 160–161 °C; 1H-NMR (600 MHz, DMSO) δ 7.97 (1H, NH), 7.73 (s, 1H), 7.68 (d, J = 7.7 Hz, 1H), 7.36 (t, J = 7.6 Hz, 1H), 7.30 (s, 1H), 7.26 (d, J = 7.4 Hz, 1H), 4.43 (m, 1H), 3.13 (ddd, J = 23.2, 14.6, 6.6 Hz, 2H), 2.37 (s, 3H), 1.79 (s, 3H). 13C-NMR (151 MHz, DMSO) δ 173.32, 168.80, 165.97, 154.70, 138.51, 133.24, 130.66, 129.08, 126.42, 123.28, 115.31, 52.99, 33.75, 22.61, 20.91; ESI+-MS: 305.0960 (calculated: 305.0954 for C15H16N2O3S [M + H]+); m/z (%): 327 (85.3, [M + Na]+), 307 (4.4, [M + 3H]+), 306 (16.5, [M + 2H]+), 305 (100, [M + H]+), 292 (3.0), 291 (21.2), 288 (4.2), 284 (1.7), 263 (30.4), 251 (21.8), 210 (4.8).", "doi": "10.3390/molecules21010025" } }, { "name": "2-Amino-3-(2-p-tolylthiazol-4-yl)propanoic acid (rac-6c)", "yield": 92, "molecularFormula": "C13H14N2O2S", "appearance": "white powder", "mp": { "low": 180, "high": 190, "units": "°C" }, "nmr1H": { "solvent": "D2O", "frequency": 600, "peaks": [ { "deltaFrom": 7.72, "multiplicity": "d", "couplings": [ 8.1 ], "assignment": "2H" }, { "deltaFrom": 7.69, "multiplicity": "s", "assignment": "1H" }, { "deltaFrom": 7.34, "multiplicity": "d", "couplings": [ 8.1 ], "assignment": "2H" }, { "deltaFrom": 4.45, "multiplicity": "t", "couplings": [ 6.9 ], "assignment": "1H" }, { "deltaFrom": 3.5, "multiplicity": "ddd", "couplings": [ 22.8, 16.5, 6.9 ], "assignment": "2H" }, { "deltaFrom": 2.32, "multiplicity": "s", "assignment": "3H" } ] }, "nmr13C": { "solvent": "D2O", "frequency": 151, "peaks": [ { "delta": 172.29 }, { "delta": 170.18 }, { "delta": 145.07 }, { "delta": 143.56 }, { "delta": 130.38 }, { "delta": 127.38 }, { "delta": 124.49 }, { "delta": 120.25 }, { "delta": 51.82 }, { "delta": 28.8 }, { "delta": 20.78 } ] }, "mass": { "peaks": [ { "mass": 263.0855, "intensity": 100, "assignment": "[M + H]+" }, { "mass": 263, "intensity": 3, "assignment": "[M + H]+" }, { "mass": 217, "intensity": 0.9 } ] }, "bp": { "high": 286, "low": 280, "units": "°C" }, "ir": { "peaks": [ { "wavenumber": null, "assignment": null } ] }, "hrms": { "expected": 263.0849, "found": 263.0855 }, "reference": null, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. \nOnly provide the YAML and remove all empty, null or undefined properties.\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Amino-3-(2-p-tolylthiazol-4-yl)propanoic acid (rac-6c): Yield: 92%; white powder; m.p. 180–190 °C for the hydrochloride salt, respectively m.p. 280–286 °C with decomposition for the free amino acid; 1H-NMR (600 MHz, D2O) δ 7.72 (d, J = 8.1 Hz, 2H), 7.69 (s, 1H), 7.34 (d, J = 8.1 Hz, 2H), 4.45 (t, J = 6.9 Hz, 1H), 3.50 (ddd, J = 22.8, 16.5, 6.9 Hz, 2H), 2.32 (s, 3H). 13C-NMR (151 MHz, D2O) δ 172.29, 170.18, 145.07, 143.56, 130.38, 127.38, 124.49, 120.25, 51.82, 28.80, 20.78; ESI+-MS: 263.0855 (calculated: 263.0849 for C13H14N2O2S [M + H]+); m/z (%): 277 (100), 263 (3.0, [M + H]+), 217 (0.9).", "doi": "10.3390/molecules21010025" } }, { "name": "2-Acetamido-3-(2-p-tolylthiazol-4-yl)propanoic acid (rac-3c)", "yield": 67, "appearance": "white solid", "mp": { "low": 181, "high": 182, "units": "°C" }, "nmr1H": { "solvent": "DMSO", "frequency": 600, "peaks": [ { "deltaFrom": 8.17, "multiplicity": "1H", "assignment": "NH" }, { "deltaFrom": 7.8, "multiplicity": "d", "couplings": [ 8.1 ], "integration": 2 }, { "deltaFrom": 7.31, "multiplicity": "s", "assignment": "1H" }, { "deltaFrom": 7.3, "multiplicity": "d", "couplings": [ 8 ], "integration": 2 }, { "deltaFrom": 4.56, "multiplicity": "dd", "couplings": [ 13.2, 8.3 ], "integration": 1 }, { "deltaFrom": 3.12, "multiplicity": "ddd", "couplings": [ 23.6, 14.6, 6.9 ], "integration": 2 }, { "deltaFrom": 2.35, "multiplicity": "s", "integration": 3 }, { "deltaFrom": 1.8, "multiplicity": "s", "integration": 3 } ] }, "nmr13C": { "solvent": "DMSO", "frequency": 151, "peaks": [ { "delta": 173.03 }, { "delta": 169.17 }, { "delta": 166.41 }, { "delta": 153.52 }, { "delta": 139.88 }, { "delta": 130.57 }, { "delta": 129.72 }, { "delta": 125.99 }, { "delta": 115.5 }, { "delta": 51.98 }, { "delta": 33.03 }, { "delta": 22.44 }, { "delta": 20.93 } ] }, "mass": { "peaks": [ { "mass": 305.0967, "assignment": "calculated: 305.0954, for C15H16N2O3S [M + H]+" } ], "ionization": "ESI+", "mode": "MS", "analyser": "-", "conditions": "-", "hrms": { "expected": null, "found": null } }, "bp": { "units": null, "pressure": null, "pressureUnits": null }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Acetamido-3-(2-p-tolylthiazol-4-yl)propanoic acid (rac-3c): Yield: 67%; white solid; m.p. 181–182 °C; 1H-NMR (600 MHz, DMSO) δ 8.17 (1H, NH), 7.80 (d, J = 8.1 Hz, 2H), 7.31 (s, 1H), 7.30 (d, J = 8.0 Hz, 2H), 4.56 (dd, J = 13.2, 8.3 Hz, 1H), 3.12 (ddd, J = 23.6, 14.6, 6.9 Hz, 2H), 2.35 (s, 3H), 1.80 (s, 3H). 13C-NMR (151 MHz, DMSO) δ 173.03, 169.17, 166.41, 153.52, 139.88, 130.57, 129.72, 125.99, 115.50, 51.98, 33.03, 22.44, 20.93; ESI+-MS: 305.0967 (calculated: 305.0954, for C15H16N2O3S [M + H]+); m/z (%): 343 (100, [M + K]+), 327 (25.4, [M + Na]+), 307 (0.8, [M + 3H]+), 306 (3.2, [M + 2H]+), 305 (18.5, [M + H]+), 291 (0.9), 284 (1.8), 263 (1.5), 251 (1.3), 210 (0.2).", "doi": "10.3390/molecules21010025" } }, { "name": "2-Acetamido-3-(2-p-clorophenylthiazol-4-yl)propanoic acid (rac-3d)", "yield": 64, "molecularFormula": "C14H13ClN2O3S", "appearance": "white solid", "mp": { "low": 199, "high": 200, "units": "°C" }, "nmr1H": { "solvent": "DMSO", "frequency": 600, "peaks": [ { "deltaFrom": 8.2, "multiplicity": "1H", "assignment": "NH" }, { "deltaFrom": 7.92, "multiplicity": "d", "couplings": [ 7.2 ], "integration": 2 }, { "deltaFrom": 7.55, "multiplicity": "d", "couplings": [ 6.8 ], "integration": 2 }, { "deltaFrom": 7.4, "multiplicity": "s", "integration": 1 }, { "deltaFrom": 4.57, "multiplicity": "dd", "couplings": [ 11.9, 8.9 ], "integration": 1 }, { "deltaFrom": 3.13, "multiplicity": "ddd", "couplings": [ 23.6, 14.6, 7 ], "integration": 2 }, { "deltaFrom": 1.8, "multiplicity": "s", "integration": 3 } ] }, "nmr13C": { "solvent": "DMSO", "frequency": 151, "peaks": [ { "delta": 173.03, "assignment": null }, { "delta": 169.29, "assignment": null }, { "delta": 164.98, "assignment": null }, { "delta": 153.89, "assignment": null }, { "delta": 134.63, "assignment": null }, { "delta": 131.98, "assignment": null }, { "delta": 129.28, "assignment": null }, { "delta": 127.77, "assignment": null }, { "delta": 116.7, "assignment": null }, { "delta": 51.99, "assignment": null }, { "delta": 33.01, "assignment": null }, { "delta": 22.46, "assignment": null } ] }, "mass": { "peaks": [ { "mass": 325.0408, "assignment": "calculated: 325.0408, for C14H13ClN2O3S [M + H]+" }, { "mass": 347, "intensity": 12.5, "assignment": "[M + Na]+" }, { "mass": 328, "intensity": 11.1, "assignment": "[M + 2H]+, 37Cl" }, { "mass": 327, "intensity": 70.1, "assignment": "[M + H]+, 37Cl" }, { "mass": 326, "intensity": 3.2, "assignment": "[M + 2H]+, 35Cl" }, { "mass": 325, "intensity": 21.4, "assignment": "[M + H]+, 35Cl" }, { "mass": 313, "intensity": 9.5 }, { "mass": 305, "intensity": 32.6 }, { "mass": 251, "intensity": 18.7 }, { "mass": 210, "intensity": 3.7 } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Acetamido-3-(2-p-clorophenylthiazol-4-yl)propanoic acid (rac-3d): Yield: 64%; white solid; m.p. 199–200 °C; 1H-NMR (600 MHz, DMSO) δ 8.20 (1H, NH), 7.92 (d, J = 7.2 Hz, 2H), 7.55 (d, J = 6.8 Hz, 2H), 7.40 (s, 1H), 4.57 (dd, J = 11.9, 8.9 Hz, 1H), 3.13 (ddd, J = 23.6, 14.6, 7.0 Hz, 2H), 1.80 (s, 3H). 13C-NMR (151 MHz, DMSO) δ 173.03, 169.29, 164.98, 153.89, 134.63, 131.98, 129.28, 127.77, 116.70, 51.99, 33.01, 22.46; ESI+-MS: 325.0408 (calculated: 325.0408, for C14H13ClN2O3S [M + H]+); m/z (%): 347 (12.5, [M + Na]+), 328 (11.1, [M + 2H]+, 37Cl), 327 (70.1, [M + H]+, 37Cl), 326 (3.2, [M + 2H]+, 35Cl), 325 (21.4, [M + H]+, 35Cl), 313 (9.5), 305 (32.6), 251 (18.7), 210 (3.7).", "doi": "10.3390/molecules21010025" } }, { "name": "Ethyl 2-acetamido-3-(2-phenylthiazol-4-yl)propanoate (rac-4a)", "yield": 64, "molecularFormula": "C16H18N2O3S", "appearance": "white solid", "mp": { "low": 116, "high": 117, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 7.94, "multiplicity": "d", "couplings": [ 4 ], "assignment": "2H" }, { "deltaFrom": 7.45, "deltaTo": 7.46, "multiplicity": "m", "couplings": [], "assignment": "3H" }, { "deltaFrom": 7.02, "multiplicity": "s", "couplings": [], "assignment": "1H" }, { "deltaFrom": 4.91, "deltaTo": 4.94, "multiplicity": "m", "couplings": [], "assignment": "1H" }, { "deltaFrom": 4.19, "multiplicity": "q", "couplings": [ 7.1 ], "assignment": "2H" }, { "deltaFrom": 3.37, "multiplicity": "ddd", "couplings": [ 17.4, 14.4, 3.7 ], "assignment": "2H" }, { "deltaFrom": 2.04, "multiplicity": "s", "couplings": [], "assignment": "3H" }, { "deltaFrom": 1.24, "multiplicity": "t", "couplings": [ 7.1 ], "assignment": "3H" } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": 151, "peaks": [ { "delta": 171.32, "assignment": "" }, { "delta": 170.19, "assignment": "" }, { "delta": 168.65, "assignment": "" }, { "delta": 152.31, "assignment": "" }, { "delta": 133.18, "assignment": "" }, { "delta": 130.7, "assignment": "" }, { "delta": 129.25, "assignment": "" }, { "delta": 126.68, "assignment": "" }, { "delta": 115.93, "assignment": "" }, { "delta": 61.67, "assignment": "" }, { "delta": 52.16, "assignment": "" }, { "delta": 32.84, "assignment": "" }, { "delta": 23.42, "assignment": "" }, { "delta": 14.33, "assignment": "" } ] }, "mass": { "peaks": [ { "mass": 319.1121, "assignment": "[M + H]+" } ], "ionization": "ESI+", "conditions": "" }, "hrms": { "expected": 319.1111, "found": 319.1121 }, "bp": {}, "ir": { "peaks": [ { "wavenumber": null } ], "conditions": "" }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "Ethyl 2-acetamido-3-(2-phenylthiazol-4-yl)propanoate (rac-4a): Yield: 64%; white solid; m.p. 116–117 °C; 1H-NMR (600 MHz, CDCl3) δ 7.94 (d, J = 4.0 Hz, 2H), 7.45–7.46 (m, 3H), 7.02 (s, 1H), 4.91–4.94 (m, 1H), 4.19 (q, J = 7.1 Hz, 2H), 3.37 (ddd, J = 17.4, 14.4, 3.7 Hz, 2H), 2.04 (s, 3H), 1.24 (t, J = 7.1 Hz, 3H). 13C-NMR (151 MHz, CDCl3) δ 171.32, 170.19, 168.65, 152.31, 133.18, 130.70, 129.25, 126.68, 115.93, 61.67, 52.16, 32.84, 23.42, 14.33; ESI+-MS: 319.1121 (calculated: 319.1111 for C16H18N2O3S [M + H]+); m/z (%): 357 (44.3, [M + K]+), 341 (16.5, [M + Na]+), 320 (18.8, [M + 2H]+), 319 (100, [M + H]+), 305 (10), 277 (14).", "doi": "10.3390/molecules21010025" } }, { "name": "Ethyl 2-acetamido-3-(2-m-tolylthiazol-4-yl)propanoate (rac-4b)", "yield": 63, "appearance": "yellow solid", "mp": { "low": 81, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 7.72, "multiplicity": "s", "assignment": "1H" }, { "deltaFrom": 7.7, "multiplicity": "d", "couplings": [ 7.8 ], "assignment": "1H" }, { "deltaFrom": 7.32, "multiplicity": "t", "couplings": [ 7.6 ], "assignment": "1H" }, { "deltaFrom": 7.24, "multiplicity": "d", "couplings": [ 7.5 ], "assignment": "1H" }, { "deltaFrom": 6.97, "multiplicity": "s", "assignment": "1H" }, { "deltaFrom": 4.92, "multiplicity": "dd", "couplings": [ 12.9, 5.2 ], "assignment": "1H" }, { "deltaFrom": 4.18, "multiplicity": "q", "couplings": [ 7.1 ], "assignment": "2H" }, { "deltaFrom": 3.32, "multiplicity": "ddd", "couplings": [ 46, 14.8, 5.2 ], "assignment": "2H" }, { "deltaFrom": 2.41, "multiplicity": "s", "assignment": "3H" }, { "deltaFrom": 2.03, "multiplicity": "s", "assignment": "3H" }, { "deltaFrom": 1.22, "multiplicity": "t", "couplings": [ 7.1 ], "assignment": "3H" } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": 151, "peaks": [ { "delta": 171.4, "assignment": null }, { "delta": 170.05, "assignment": null }, { "delta": 168.6, "assignment": null }, { "delta": 152.47, "assignment": null }, { "delta": 138.88, "assignment": null }, { "delta": 133.22, "assignment": null }, { "delta": 131.18, "assignment": null }, { "delta": 129.03, "assignment": null }, { "delta": 127.12, "assignment": null }, { "delta": 123.7, "assignment": null }, { "delta": 115.61, "assignment": null }, { "delta": 61.56, "assignment": null }, { "delta": 52.12, "assignment": null }, { "delta": 33.03, "assignment": null }, { "delta": 23.36, "assignment": null }, { "delta": 21.49, "assignment": null }, { "delta": 14.27, "assignment": null } ] }, "mass": { "peaks": [ { "mass": 333.127, "intensity": null, "assignment": null } ], "ionization": "ESI+", "conditions": null }, "hrms": { "assignment": null, "expected": null, "found": null }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "Ethyl 2-acetamido-3-(2-m-tolylthiazol-4-yl)propanoate (rac-4b): Yield: 63%; yellow solid; m.p. 81 °C; 1H-NMR (600 MHz, CDCl3) δ 7.72 (s, 1H), 7.70 (d, J = 7.8 Hz, 1H), 7.32 (t, J = 7.6 Hz, 1H), 7.24 (d, J = 7.5 Hz, 1H), 6.97 (s, 1H), 4.92 (dd, J = 12.9, 5.2 Hz, 1H), 4.18 (q, J = 7.1 Hz, 2H), 3.32 (ddd, J = 46.0, 14.8, 5.2 Hz, 2H), 2.41 (s, 3H), 2.03 (s, 3H), 1.22 (t, J = 7.1 Hz, 3H). 13C-NMR (151 MHz, CDCl3) δ 171.40, 170.05, 168.60, 152.47, 138.88, 133.22, 131.18, 129.03, 127.12, 123.70, 115.61, 61.56, 52.12, 33.03, 23.36, 21.49, 14.27. ESI+-MS: 333.1270 (calculated: 333.1267 for C17H20N2O3S [M + H]+); m/z (%): 371 (61.0, [M + K]+), 355 (36.9, [M + Na]+), 334 (19.8, [M + 2H]+), 333 (100.0, [M + H]+), 319 (2.7), 305 (1), 291 (6.2).", "doi": "10.3390/molecules21010025" } }, { "name": "Ethyl 2-acetamido-3-(2-p-tolylthiazol-4-yl)propanoate (rac-4c)", "yield": 65, "appearance": "white solid", "mp": { "low": 98, "units": "°C" }, "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 7.78, "multiplicity": "d", "couplings": [ 8 ], "integration": 2 }, { "deltaFrom": 7.24, "multiplicity": "d", "couplings": [ 7.9 ], "integration": 2 }, { "deltaFrom": 6.94, "multiplicity": "s", "integration": 1 }, { "deltaFrom": 4.91, "multiplicity": "dt", "couplings": [ 7.5, 5.1 ], "integration": 1 }, { "deltaFrom": 4.18, "multiplicity": "q", "couplings": [ 7.1 ], "integration": 2 }, { "deltaFrom": 3.31, "multiplicity": "ddd", "couplings": [ 50.6, 14.8, 5 ], "integration": 2 }, { "deltaFrom": 2.4, "multiplicity": "s", "integration": 3 }, { "deltaFrom": 2.04, "multiplicity": "s", "integration": 3 }, { "deltaFrom": 1.22, "multiplicity": "t", "couplings": [ 7.1 ], "integration": 3 } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": 151, "peaks": [ { "delta": 171.45 }, { "delta": 170.07 }, { "delta": 168.56 }, { "delta": 152.54 }, { "delta": 140.6 }, { "delta": 130.96 }, { "delta": 129.81 }, { "delta": 126.42 }, { "delta": 115.22 }, { "delta": 61.58 }, { "delta": 52.15 }, { "delta": 33.11 }, { "delta": 23.43 }, { "delta": 21.56 }, { "delta": 14.31 } ] }, "mass": { "peaks": [ { "mass": 333.1265, "assignment": "C17H20N2O3S [M + H]+" } ], "ionization": "ESI+", "mode": "+", "analyser": "MS", "conditions": "calculated: 333.1267 for C17H20N2O3S [M + H]+" }, "bp": { "pressureUnits": null }, "hrms": { "found": null, "expected": null }, "ir": { "peaks": [] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "Ethyl 2-acetamido-3-(2-p-tolylthiazol-4-yl)propanoate (rac-4c): Yield: 65%; white solid; m.p. 98 °C; 1H-NMR (600 MHz, CDCl3) δ 7.78 (d, J = 8.0 Hz, 2H), 7.24 (d, J = 7.9 Hz, 2H), 6.94 (s, 1H), 4.91 (dt, J = 7.5, 5.1 Hz, 1H), 4.18 (q, J = 7.1 Hz, 2H), 3.31 (ddd, J = 50.6, 14.8, 5.0 Hz, 2H), 2.40 (s, 3H), 2.04 (s, 3H), 1.22 (t, J = 7.1 Hz, 3H). 13C-NMR (151 MHz, CDCl3) δ 171.45, 170.07, 168.56, 152.54, 140.60, 130.96, 129.81, 126.42, 115.22, 61.58, 52.15, 33.11, 23.43, 21.56, 14.31; ESI+-MS: 333.1265 (calculated: 333.1267 for C17H20N2O3S [M + H]+); m/z (%): 371 (12.1, [M + K]+), 355 (47.6, [M + Na]+), 334 (21.5, [M + 2H]+), 333 (100.0, [M + H]+), 319 (35), 305 (17.5), 291 (5), 259 (12.0), 253 (22.9), 217 (24.9).", "doi": "10.3390/molecules21010025" } }, { "name": "n-Propyl 2-acetamido-3-(2-p-chlorophenylthiazol-4-yl)propanoate (rac-4d)", "yield": 64, "molecularFormula": "C17H19ClN2O3S", "appearance": "white solid", "nmr1H": { "solvent": "CDCl3", "frequency": 600, "peaks": [ { "deltaFrom": 7.86, "multiplicity": "d", "couplings": [ 8.5 ], "integration": 2 }, { "deltaFrom": 7.4, "multiplicity": "d", "couplings": [ 8.5 ], "integration": 2 }, { "deltaFrom": 6.97, "multiplicity": "s", "integration": 1 }, { "deltaFrom": 4.94, "multiplicity": "dt", "couplings": [ 7.7, 5.1 ], "integration": 1 }, { "deltaFrom": 4.08, "multiplicity": "t", "couplings": [ 6.7 ], "integration": 2 }, { "deltaFrom": 2.02, "multiplicity": "s", "integration": 3 }, { "deltaFrom": 1.73, "deltaTo": 1.65, "multiplicity": "m", "integration": 2 }, { "deltaFrom": 0.89, "multiplicity": "t", "couplings": [ 7.4 ], "integration": 3 } ] }, "nmr13C": { "solvent": "CDCl3", "frequency": 151, "peaks": [ { "delta": 171.55 }, { "delta": 170.34 }, { "delta": 168.02 }, { "delta": 153.77 }, { "delta": 148.43 }, { "delta": 131.36 }, { "delta": 129.35 }, { "delta": 127.67 }, { "delta": 115.97 }, { "delta": 67.24 }, { "delta": 52.07 }, { "delta": 34.06 }, { "delta": 23.4 }, { "delta": 21.7 }, { "delta": 10.46 } ] }, "mass": { "peaks": [ { "mass": 367.0879, "assignment": "[M + H]+" }, { "mass": 405, "assignment": "[M + K]+" }, { "mass": 389, "assignment": "[M + Na]+" }, { "mass": 370, "intensity": 6.6, "assignment": "[M + 2H]+, 37Cl" }, { "mass": 369, "intensity": 37.2, "assignment": "[M + H]+, 37Cl" }, { "mass": 368, "intensity": 19.5, "assignment": "[M + 2H]+, 35Cl" }, { "mass": 367, "intensity": 100, "assignment": "[M + H]+, 35Cl" }, { "mass": 333, "intensity": 10 }, { "mass": 319, "intensity": 1.8 }, { "mass": 305, "intensity": 1.7 }, { "mass": 287, "intensity": 1.5 }, { "mass": 244, "intensity": 1.8 } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. Remove all empty properties.\nOnly provide the YAML\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "n-Propyl 2-acetamido-3-(2-p-chlorophenylthiazol-4-yl)propanoate (rac-4d): Yield: 64%; white solid; 1H-NMR (600 MHz, CDCl3) δ 7.86 (d, J = 8.5 Hz, 2H), 7.40 (d, J = 8.5 Hz, 2H), 6.97 (s, 1H), 4.94 (dt, J = 7.7, 5.1 Hz, 1H), 4.08 (t, J = 6.7 Hz, 2H), 2.02 (s, 3H), 1.73–1.65 (m, 2H), 0.89 (t, J = 7.4 Hz, 3H). 13C-NMR (151 MHz, CDCl3) δ 171.55, 170.34, 168.02, 153.77, 148.43, 131.36, 129.35, 127.67, 115.97, 67.24, 52.07, 34.06, 23.40, 21.70, 10.46; ESI+-MS: 367.0879 (calculated: 367.0878 for C17H19ClN2O3S [M + H]+); m/z (%): 405 ([M + K]+), 389 ([M + Na]+), 370 (6.6, [M + 2H]+, 37Cl), 369 (37.2, [M + H]+, 37Cl), 368 (19.5, [M + 2H]+, 35Cl), 367 (100, [M + H]+, 35Cl), 333 (10), 319 (1.8), 305 (1.7), 287 (1.5), 244 (1.8).", "doi": "10.3390/molecules21010025" } }, { "name": "2-Amino-3-(2-phenylthiazol-4-yl)propanoic acid (rac-6a)", "yield": 91, "molecularFormula": "C12H12N2O2S", "appearance": "white powder", "mp": { "low": 241, "high": 248, "units": "°C" }, "nmr1H": { "solvent": "D2O", "frequency": 600, "peaks": [ { "deltaFrom": 7.82, "deltaTo": 7.79, "multiplicity": "m", "assignment": "2H" }, { "deltaFrom": 7.62, "deltaTo": 7.38, "multiplicity": "m", "assignment": "4H" }, { "deltaFrom": 4.44, "multiplicity": "t", "couplings": [ 6.5 ], "integration": 1, "assignment": "1H" }, { "deltaFrom": 3.45, "multiplicity": "ddd", "couplings": [ 22.5, 15.6, 6.4 ], "integration": 2, "assignment": "2H" } ] }, "nmr13C": { "solvent": "D2O", "frequency": 151, "peaks": [ { "delta": 172.4, "assignment": null }, { "delta": 170.98, "assignment": null }, { "delta": 170.67, "assignment": null }, { "delta": 146.59, "assignment": null }, { "delta": 132, "assignment": null }, { "delta": 129.5, "assignment": null }, { "delta": 126.9, "assignment": null }, { "delta": 119.69, "assignment": null }, { "delta": 52.24, "assignment": null }, { "delta": 29.84, "assignment": null } ] }, "hrms": { "expected": null, "found": null }, "mass": { "peaks": [ { "mass": 263, "intensity": 100, "assignment": null }, { "mass": 249, "intensity": 2.9, "assignment": "[M + H]+" }, { "mass": 203, "intensity": 1.5, "assignment": null } ] }, "source": { "prompt": "\nThis is a scientific experimental part describing a chemical molecule and we need to parse all the information.\nFirst remove the HTML tags and then convert the text to a YAML.\nThis must be very accurate and no data may be invented. \nOnly provide the YAML and remove all empty, null or undefined properties.\n\n {\n name?: string,\n reference?: string,\n yield?: number,\n molecularFormula?: string,\n appearance?: string,\n ir?: {\n peaks: [\n {wavenumber: number, assignment?: string},\n ],\n conditions?: string\n },\n mass?: {\n \tpeaks: [{mass: number, intensity?: number, assignment?: string}],\n \tionization?: string,\n \tmode?: string,\n \tanalyser?: string,\n \tconditions?: string,\n }\n hrms?: {\n assignment?: string,\n \texpected?: number,\n \tfound?: number,\n }\n bp?: {\n low?: number,\n high?: number,\n units?: string,\n pressure?: number\n pressureUnits?: string\n },\n mp?: {\n low?: number,\n high?: number,\n units?: string,\n },\n nmr1H?: {\n solvent: string,\n frequency: number,\n peaks: [\n {deltaFrom: number, deltaTo?: number, multiplicity: string, couplings?: number[], integration?: number, assignment?: string},\n ]\n },\n nmr13C?: {\n solvent: string,\n frequency: number,\n peaks: [\n {delta: number, assignment?: string},\n ]\n },\n}\n", "line": "2-Amino-3-(2-phenylthiazol-4-yl)propanoic acid (rac-6a): Yield: 91%; white powder; m.p. 241–248 °C for the hydrochloride salt, respectively m.p. over 300 °C with decomposition for the free amino acid; 1H-NMR (600 MHz, D2O) δ 7.82–7.79 (m, 2H), 7.62–7.38 (m, 4H), 4.44 (t, J = 6.5 Hz, 1H), 3.45 (ddd, J = 22.5, 15.6, 6.4 Hz, 2H). 13C-NMR (151 MHz, D2O) δ 172.4, 170.98, 170.67, 146.59, 132.00, 129.50, 126.90, 119.69, 52.24, 29.84; ESI+-MS: 249.0699 (calculated: 249.0692 for C12H12N2O2S [M + H]+); m/z (%): 263 (100), 249 (2.9, [M + H]+), 203 (1.5).", "doi": "10.3390/molecules21010025" } } ]