Experimental and computational investigations of some new cabamothioate compounds

The new derivatives of S-aryl (trichloroacetyl) carbamothioate were prepared from a two-component reaction of 2-naphthalenethiol or thiophenol derivatives and trichloroacetyl isocyanate in CH2Cl2 at room temperature at high yields. The reaction was a simple and efficient procedure with high yield and available stating materials in a short time for the synthesis of these compounds that no side reactions were observed. The structures of the products were confirmed by IR, 1H NMR, 13C NMR spectroscopy, and elemental analysis. Quantum theoretical calculations for the three structures of compounds (3a, 3b and 3c) were performed using the G3MP2, LC-ωPBE, MP2, and B3LYP methods with the 6-311+G(d,p) basis set. Geometric parameters of optimized the structures were compared with the experimental measurements. The structures of the products were confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. IR spectra data and 1H NMR and 13C NMR chemical shifts computations of the compounds were calculated. Frontier molecular orbitals (FMOs), total density of states (DOS), thermodynamic parameters and molecular electrostatic potentials (MEP) of the title compounds were investigated by theoretical calculations. Molecular properties such as the ionization potential (I), electron affinity (A), chemical hardness (η), electronic chemical potential (μ) and electrophilicity (ω) were investigated for the structures. Consequently, there was an excellent agreement between experimental and theoretical results.

Keywords:

Trichloroacetyl isocyanate , Carbamothioate , Thiophenol , Naphthalenethiol , DoS , Vibrational frequencies , NMR chemical shift analysis