Synthesis and characterization of N-(arylcarbamothioyl)- cyclohexanecarboxamide derivatives: The crystal structure of N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide

Abstract

A number of N-(arylcarbamothioyl)cyclohexanecarboxamide derivatives (aryl substituents: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, o-tolyl, p-tolyl, 3methoxyphenyl, 4-methoxyphenyl and naphthalen-lyl) have been synthesized. The compounds obtained were characterized by elemental analyses, IR spectroscopy and 1H-NMR spectroscopy. N-(naphthalen-1- ylcarbamothioyl)cyclohexanecarboxamide, H2L9, was also characterized by a single crystal X-ray diffraction study. This compound, C 18H20N2OS, crystallizes in the triclinic space group P1̄, with Z = 2, and unit cell parameters a = 6.9921(14) Å, b = 11.002(2) Å, c = 12.381(3) Å, α = 113.28(3)°, β = 99.38(3)°, and γ= 101.85(3)°. The cyclohexane ring adopts a chair conformation. The molecular conformation of the compound is stabilized by an intramolecular (N2-H2⋯01) hydrogen bond which forms a pseudo-six-membered ring.