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Molecules 2009, 14(2), 655-666; doi:10.3390/molecules14020655
Article

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

1, 1, 2,* , 3
 and
4
1 Department of Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR 33169, Turkey 2 Department of Natural Sciences, Fayetteville State University, Fayetteville, NC 28301, USA 3 Department of Chemistry, Clemson University, Clemson, SC 29634, USA 4 Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
* Author to whom correspondence should be addressed.
Received: 9 January 2009 / Revised: 21 January 2009 / Accepted: 5 February 2009 / Published: 10 February 2009
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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 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)°, b = 99.38(3)°, and g = 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.
Keywords: Synthesis; Cyclohexane; Thiourea; Single crystal structure; Pseudo-six-membered ring Synthesis; Cyclohexane; Thiourea; Single crystal structure; Pseudo-six-membered ring
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Özer, C.K.; Arslan, H.; VanDerveer, D.; Külcü, N. Synthesis and Characterization of N-(Arylcarbamothioyl)-cyclohexanecarboxamide Derivatives: The Crystal Structure of N-(Naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide. Molecules 2009, 14, 655-666.

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