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

Hamza M. Abosadiya, Siti Aishah Hasbullah, Bohari Mohd. Yamin

Research output: Contribution to journalArticle

9 Citations (Scopus)

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 CN bonds. The configuration is attributed by the intrahydrogen bond between the carbonyl oxygen and amide hydrogen atoms. Both crystal structures are stabilized by NH'S intermolecular hydrogen bonds to form dimers and arranged along the b axis.

Original languageEnglish
Pages (from-to)379-385
Number of pages7
JournalJiegou Huaxue
Volume34
Issue number3
DOIs
Publication statusPublished - 15 Mar 2015

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Thiourea
X rays
Dimethyl Sulfoxide
Amides
Isomers
Dimers
Hydrogen
Hydrogen bonds
Crystal structure
Crystallization
Nuclear magnetic resonance
Oxygen
Crystalline materials
Atoms
Molecules

Keywords

  • 4-bromobutyryl chloride
  • Thiourea derivatives
  • X-ray structural study

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis, characterization and X-ray structure of N-(4- bromobutanoyl-N'-(2-3- and 4-methylphenyl)thiourea. / Abosadiya, Hamza M.; Hasbullah, Siti Aishah; Mohd. Yamin, Bohari.

In: Jiegou Huaxue, Vol. 34, No. 3, 15.03.2015, p. 379-385.

Research output: Contribution to journalArticle

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AB - 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 CN bonds. The configuration is attributed by the intrahydrogen bond between the carbonyl oxygen and amide hydrogen atoms. Both crystal structures are stabilized by NH'S intermolecular hydrogen bonds to form dimers and arranged along the b axis.

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