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

• Published in: Molecules (Basel, Switzerland) Switzerland), 2009-02, Vol.14 (2), p.655-666
• Main Authors: Ozer, Cemal Koray, Arslan, Hakan, VanDerveer, Don, Külcü, Nevzat
• Format: Article
• Language: English
• Subjects: Amides - chemical synthesis; Amides - chemistry; Chemistry; Crystal structure; Crystallography, X-Ray; Cyclohexane; Hydrocarbons, Cyclic - chemical synthesis; Hydrocarbons, Cyclic - chemistry; Hydrogen Bonding; Hydrogen bonds; Molecular Conformation; Molecular Structure; Pseudo-six-membered ring; Single crystal structure; Single crystals; Synthesis; Thiourea; Vibration; X-Ray Diffraction
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules14020655

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.