Experimental and theoretical studies of a thiourea derivative: 1-(4-chloro-benzoyl)-3-(2-trifluoromethyl-phenyl)thiourea

The 1-(4-chloro-benzoyl)-3-(2-trifluoromethyl-phenyl)thiourea compound was synthesized by a two-step reaction and a single crystal of it was obtained by recrystallization method. Its structure was eluci-dated by elemental analyzes, FT-IR, 1H NMR, and 13C NMR techniques, and its molecular and crystal structure was also determined by single-crystal X-ray diffraction analysis. The Hirshfeld surface ana-lyzes of the crystal structure indicate that the most important contributions for crystal packing are from H center dot center dot center dot H (23.8%), H center dot center dot center dot S/S center dot center dot center dot H (14.5%), H center dot center dot center dot F/F center dot center dot center dot H (14.3%), C center dot center dot center dot H/H center dot center dot center dot C (14.2%), and Cl center dot center dot center dot F/F center dot center dot center dot Cl (9.0%). In addition, energy-framework calculations are used to analyze and visualize the three-dimensional topology of the crystal packing. The electrostatic energy framework is dominant over the dispersion energy framework. The density functional theory method with the basis set of B3LYP/6-311G(d,p) has been employed to obtain the optimized structural geometry, Mulliken charges, molecular electrostatic potential, frontier molecular orbitals, the total density of states, reduced density gradient analysis and natural bond orbitals. The experimental crystal structure parameters and optimized structure parameters are very similar. The HOMO-LUMO energy gap of the compound is 3.5307 eV. Different global chemical reactivity descriptor parameters were also calculated. Nonlinear optical properties such as anisotropy of polarizability, mean polarizability, static dipole moment, and first-order hyperpolarizability values were theoretically deter-mined. The Fukui functions as electron density-based local reactivity descriptors were also calculated to explain the chemical selectivity or the reactivity site in the molecule. Molecular docking studies were also carried out to determine the inhibitory action of the title compound against the main protease (6LU7) of a new coronavirus (COVID-19). (c) 2023 Elsevier B.V. All rights reserved.