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

Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, No. 5 Jalan Universiti, Bandar Sunway 47500, Selangor Darul Ehsan, Malaysia
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Molbank 2019, 2019(1), M1047; https://doi.org/10.3390/M1047
Received: 18 January 2019 / Revised: 18 February 2019 / Accepted: 19 February 2019 / Published: 19 February 2019
(This article belongs to the Section Structure Determination)
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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. View Full-Text
Keywords: 1,2,4-triazole-5-thione; hetero-cyclization reaction; hydrogen bonding; X-ray crystallography 1,2,4-triazole-5-thione; hetero-cyclization reaction; hydrogen bonding; X-ray crystallography
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Yeo, C.I.; Azizan, A.H.S.; Tiekink, E.R. 4-(4-Chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione. Molbank 2019, 2019, M1047.

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