Synthesis and Characterization of N-(Arylcarbamothioyl)-cyclohexanecarboxamide Derivatives: The Crystal Structure of N-(Naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide

Molecules

Cemal Koray Özer²  Hakan Arslan²  Don VanDerveer¹ 

[1] Department of Chemistry, Clemson University, Clemson, SC 29634, USA; E-mail:Department of Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR 33169, Turkey;

关键词: Synthesis;    Cyclohexane;    Thiourea;    Single crystal structure;    Pseudo-six-membered ring;   

DOI  :  10.3390/molecules14020655

来源: mdpi

【 摘 要 】

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 ¹H-NMR spectroscopy. N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide, H₂L⁹, was also characterized by a single crystal X-ray diffraction study. This compound, C₁₈H₂₀N₂OS, crystallizes in the triclinic space group Pī, 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•••O1) hydrogen bond which forms a pseudo-six-membered ring.

【 授权许可】

CC BY   
© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.