Synthesis and Theoretical Characterization of 4-(p-tollyl)-5(thiophen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione Using Experimental and Quantum Chemical Calculations

Abstract

The aim of the study was to synthesize 4- (p-tollyl) -5- (thiophene-2-yl) -2,4-dihydro-3H-1,2,4-triazole3-thione and detect its experimental and the quantum chemical properties. 4-(p-tollil)-5-(tiyofen-2-il)-2,4dihidro-3H-1,2,4-triazole-3-tiyon was synthesized using by the nucleophilic sübstitüsyon reaction. The synthesized title compound has been characterized both experimentally and theoretically using quantum chemical calculations and spectral techniques. The molecular geometry, vibrational frequencies, and 1H and 13C NMR chemical shifts of the title compound in the ground state were calculated using the density functional method (B3LYP) with the 6–311G(d, p) basis set. It was seen that the calculated infrared and nuclear magnetic resonance values were compatible with the experimental values. To determine conformational flexibility, the molecular energy profile of 4- (p-tollyl) -5- (thiophene-2-yl) -2,4-dihydro3H-1,2,4-triazole-3-thione was obtained by DFT calculations with respect to the selected torsion angle, which was varied from 180°to +180°in steps of 20°. In addition, the HOMO- LUMO energies of this conformational structure were calculated.