Abstract
A simple efficient method for synthesis of some new 1,2,4-Triazole and Triazolidin derivatives namely, 5-(4-methoxyphenyl)-2-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (1a), (2-chlorophenyl)(3,3-dimethyl-1-phenyl-5-thioxo-1,2,4-triazolidin-4-yl)methanone (1b) and (2-iodophenyl)(3,3-dimethyl-1-phenyl-5-thioxo-1,2,4-triazolidin-4-yl)methanone (1c) have been synthesized in high yields from the reaction of carbonoyl isothiocyanate with phenyl hydrazine. The final products were characterized by FT-IR, 1H and 13C NMR spectroscopic techniques. X-ray crystallographic studies showed that 1a crystallized in triclinic crystal system with space group Pī, while both 1b and 1c crystallized in orthorhombic crystal system with space group Pna21. The asymmetric unit of 1a consists two crystallographically independent molecules, while only one molecule in asymmetric unit for both 1b and 1c compounds. All molecules possess CH ….S intramolecular hydrogen bonds which formed a pseudo-six-membered ring. Experimental results have been confirmed by the state-of-art density functional theory (DFT) in gas and solvent phase by using five different hybrid functionals B3LYP, B3P86, CAM-B3LYP, M06-2X and PBE0 combined with 6–311++G(d, p) basis set. The experimental data are relatively well produced, and relatively good correlations are obtained between the predicted and experimental data.
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•Synthesis of three new 1,2,4-Triazole and Triazolidin derivatives.•They were characterized using X-ray and spectroscopic techniques.•Experimental data are supported by DFT calculations.•A synthesis mechanism has been proposed.