Experimental and theoretical investigation of N-(4-nitrobenzoyl)-S-(cyclohexyl)-dithiocarbamate, N-(4-nitrobenzoyl)-S-benzyldithiocarbamate

Abstract

Two new dithiocarbamate molecules were synthesized and characterized by 1H NMR, 13C NMR, IR, and structural X-ray diffraction techniques. The molecular geometry, vibrational frequencies of the title compounds in the ground state have been calculated by using the Hartree-Fock (HF) and density functional theory (DFT) methods with 6–31G(d) basis set, also gauge-independent atomic orbital (GIAO) 1H and 13C NMR chemical shift values of the title compound (I) have been calculated by the same methods and compared with the experimental data. The calculated results show that the optimized geometries can well reproduce the crystal structural parameters. A detailed vibrational spectral analysis has been carried out and assignments of observed fundamental bands have been proposed on basis of peak positions. The scaled theoretical frequencies showed very good agreement with experimental values. In addition, the computed 1H and 13C NMR chemical shift values are in line with experimental data. To determine conformational flexibility, the molecular energy profile of the title compounds were obtained in respect of the selected torsion angle, which were varied from −180° to +180° in steps of 10°. Besides, frontier molecular orbitals (FMO), molecular electrostatic potential (MEP)analysis and thermodynamic properties were investigated by theoretical calculations.