Synthesis, X-ray crystal structure and theoretical study of 4-ethyl-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione; structural comparison with its aromatic analogs
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Irena Wawrzycka-Gorczyca
Abstract
The crystal structure of 4-ethyl-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (1) was determinäed. The compound crystallizes in the monoclinic space group P21/n (Z = 4) with a = 8.679(2), b = 7.873(2), c = 14.657(3) Å, β = 105.56(3)° and V = 964.8(4) Å3. Its molecular and crystal structure was compared with three aromatic analogs. In three crystal structures of 2,4-dihydro-3H-1,2,4-triazole-3-thione derivatives, Ntriazole—H · · · S(=C) dimer as the main structural motif is formed, while in one Ntriazole—H · · · S hydrogen bonds connect molecules to make helix arrangement. Moreover, in 1, Cethyl—H · · · S(=C), Sthione · · · Sthiophene and πthiophene · · · πtriazole interactions are observed; there are not N—H · · · N hydrogen bonds.
NMR in DMSO and IR experiments confirmed the compound to exist as the thione tautomer.
We carried out extensive conformational searches for 1 at the molecular mechanics level in order to compare structures obtained from different force fields with the experimental results.
© by Oldenbourg Wissenschaftsverlag, Lublin, Germany
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- Synthesis, X-ray crystal structure and theoretical study of 4-ethyl-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione; structural comparison with its aromatic analogs
Articles in the same Issue
- Crystal structure of the ternary compound γ-Al3FeSi
- Ab initio study of the properties of CuAlSe2: A chalcopyrite compound
- Crystal structures of thiazine-indigo pigments, determined from single-crystal and powder diffraction data
- Structural characterization of arbidol®
- (2-Amidoethyl)trichlorotin(IV)complexes with amido ligands and chloride ion: supramolecular arrays from H-bonds involving the amido and chloride ions
- Crystal structures of hydrazones, 2-(1,3-benzothiazolyl)-NH—N=CH—Ar, prepared from arenealdehydes and 2-hydrazinyl-1,3-benzothiazole
- Synthesis, X-ray crystal structure and theoretical study of 4-ethyl-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione; structural comparison with its aromatic analogs
