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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
Received: 9 January 2009; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Özer CK, 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(2):655-666.

Chicago/Turabian Style

Özer, Cemal Koray; Arslan, Hakan; VanDerveer, Don; Külcü, Nevzat. 2009. "Synthesis and Characterization of N-(Arylcarbamothioyl)-cyclohexanecarboxamide Derivatives: The Crystal Structure of N-(Naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide." Molecules 14, no. 2: 655-666.



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