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

Abstract

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.