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 shu

Synthesis, Characterization and X-ray Structure of N-(4-bromobutanoyl-N'-(2-3-and 4-methylphenyl)thiourea

1.
School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43650 Bangi, Selangor Malaysia

Corresponding author: Siti Aishah Hasbullah,
Received Date: 15 September 2014
Available Online: 6 January 2015
Fund Project:

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.
- 4-bromobutyryl chloride,
- thiourea derivatives,
- X-ray structural study
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