4-(4-Chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione

Yeo, Chien Ing * and Azizan, Ainnul H S * and Tiekink, Edward R. T. * (2019) 4-(4-Chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione. Molbank, 1. p. 1047. ISSN 1422-8599

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Abstract

The title compound, 4-(4-chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione (1), was synthesized by a hetero-cyclization reaction of 4-chlorophenyl isothiocyanate and formic hydrazide. Compound 1 was characterized by a single-crystal X-ray structure determination as well as 1H and 13C{1H} NMR, IR, and UV spectroscopy, and microelemental analysis. X-ray crystallography on 1 confirms the molecule exists as the thione tautomer and shows the five-membered ring to be planar and to form a dihedral angle of 82.70(5)° with the appended chlorophenyl ring, indicating an almost orthogonal relationship. In the molecular packing, supramolecular dimers are formed via thioamide-N–H⋯S(thione) hydrogen bonds and these are connected by C=S⋯π(triazolyl) and C-Cl⋯π(triazolyl) interactions, leading to a three-dimensional architecture

Item Type: Article
Uncontrolled Keywords: 1,2,4-triazole-5-thione; hetero-cyclization reaction; hydrogen bonding; X-ray crystallography
Subjects: Q Science > QD Chemistry
Divisions: Sunway University > School of Science and Technology > Research Centre for Crystalline Materials
Depositing User: Dr Janaki Sinnasamy
Related URLs:
Date Deposited: 20 Feb 2019 06:44
Last Modified: 22 Apr 2019 05:31
URI: http://eprints.sunway.edu.my/id/eprint/998

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