Citation:
Hamza M Abosadiya, Siti Aishah Hasbullah, Bohari M Yamin. Synthesis, Characterization and X-ray Structure of N-(4-bromobutanoyl-N'-(2-3-and 4-methylphenyl)thiourea[J]. Chinese Journal of Structural Chemistry,
2015, 34(3): 379-385.
doi:
10.14102/j.cnki.0254-5861.2011-0509
Synthesis, Characterization and X-ray Structure of N-(4-bromobutanoyl-N'-(2-3-and 4-methylphenyl)thiourea
摘要:
N-4-(bromobutanoyl)-N'-(o-, m-and p-tolyl)thioureas 3a, 3b and 3c respectively, were synthesized by the reaction of 4-bromobutanoylisothiocyanate with p-, m-and o-toludine. The products were characterized by IR, and NMR spectroscopic techniques. The two carbonoylthiourea isomers N-4-(bromobutanoyl)-N'-(3-methylphenyl)thiourea (3b) and N-4-(bromobutanoyl)-N'-(4-methylphenyl)thiourea (3c) were obtained in crystalline form by recrystallization from DMSO. Xray crystallographic studies showed that both compounds 3b and 3c crystallize in triclinic system with space group of P1. The molecules adopt trans-cis configuration with respect to the positions of 4-bromobutanoyl and tolyl groups respectively, against the thiono C=S bond across their C-N bonds. The configuration is attributed by the intrahydrogen bond between the carbonyl oxygen and amide hydrogen atoms. Both crystal structures are stabilized by N-H…S intermolecular hydrogen bonds to form dimers and arranged along the b axis.
English
Synthesis, Characterization and X-ray Structure of N-(4-bromobutanoyl-N'-(2-3-and 4-methylphenyl)thiourea
Abstract:
N-4-(bromobutanoyl)-N'-(o-, m-and p-tolyl)thioureas 3a, 3b and 3c respectively, were synthesized by the reaction of 4-bromobutanoylisothiocyanate with p-, m-and o-toludine. The products were characterized by IR, and NMR spectroscopic techniques. The two carbonoylthiourea isomers N-4-(bromobutanoyl)-N'-(3-methylphenyl)thiourea (3b) and N-4-(bromobutanoyl)-N'-(4-methylphenyl)thiourea (3c) were obtained in crystalline form by recrystallization from DMSO. Xray crystallographic studies showed that both compounds 3b and 3c crystallize in triclinic system with space group of P1. The molecules adopt trans-cis configuration with respect to the positions of 4-bromobutanoyl and tolyl groups respectively, against the thiono C=S bond across their C-N bonds. The configuration is attributed by the intrahydrogen bond between the carbonyl oxygen and amide hydrogen atoms. Both crystal structures are stabilized by N-H…S intermolecular hydrogen bonds to form dimers and arranged along the b axis.
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Key words:
- 4-bromobutyryl chloride
- / thiourea derivatives
- / X-ray structural study
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