Chemoselective synthesis, X-ray characterization and DFT studies of new organic single crystal: S-(2-aminophenyl) cyclohexylcarbamothioate

Chemoselective manner of 2-aminothiophenol reaction with cyclohexyl isocyanate under the different conditions was investigated. The product, S-(2-aminophenyl) cyclohexylcarbamothioate, was characterized by 1H, 13C NMR, FT-IR, HRMS and single crystal X-ray diffraction analysis. Single crystal of the molecular structure, C13H18N2OS, crystallizes in monoclinic form, space group P 21/n with a = 6.1808(4) Å, b = 24.8308(12) Å, c = 9.7080(8) Å, β = 103.674(6)°, V = 1303.73(13) Å3, F (000) = 36. The structure exhibits disorder over the phenyl ring, with site occupancies of 0.913(4) and 0.087(4) for the major and minor components, respectively. The conformation is stabilized by intra- and intermolecular N–H. . . O, N–H. . . N, and C– H. . . S hydrogen bonds into running along the a-axis. The title compound has been optimized by DFT/B3LYP/6-31 + G (d, p) basis set, and compared with experimental findings. Natural bond orbital charges of probable intramolecular hydrogen bonds have been calculated to compare with experimental data, and frontier orbital analysis and molecular electrostatic potential (MEP) analysis were also carried out. [Display omitted] •A chemoselective method, for the preparation of S-thiocarbamate derivatives, was developed.•The structure of a single crystal of S-(2-aminophenyl) cyclohexylcarbamothioate was determined.•The theoretical calculations were also compared with the experimental findings.•Frontier molecular analysis, NBO and MEP analysis of the compound were studied.