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

Molecules. 2009 Feb 10;14(2):655-66. doi: 10.3390/molecules14020655.

Abstract

A number of N-(arylcarbamothioyl)cyclohexanecarboxamide derivatives (aryl substituents: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, o-tolyl, p-tolyl, 3-methoxyphenyl, 4-methoxyphenyl and naphthalen-1yl) have been synthesized. The compounds obtained were characterized by elemental analyses, IR spectroscopy and (1)H-NMR spectroscopy. N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide, H(2)L(9), was also characterized by a single crystal X-ray diffraction study. This compound, C(18)H(20)N(2)OS, crystallizes in the triclinic space group Pī, with Z = 2, and unit cell parameters a = 6.9921(14) A, b = 11.002(2) A, c = 12.381(3) A, alpha = 113.28(3) degrees, beta = 99.38(3) degrees, and gamma = 101.85(3) degrees. The cyclohexane ring adopts a chair conformation. The molecular conformation of the compound is stabilized by an intramolecular (N2-H2***O1) hydrogen bond which forms a pseudo-six-membered ring.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Crystallography, X-Ray
  • Hydrocarbons, Cyclic / chemical synthesis
  • Hydrocarbons, Cyclic / chemistry*
  • Hydrogen Bonding
  • Molecular Conformation
  • Molecular Structure
  • X-Ray Diffraction

Substances

  • Amides
  • Hydrocarbons, Cyclic