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Updated: Feb 18, 2026

Preparation of Carbon Nanosheets at Room Temperature
Published on: March 8, 2016
Experimental Demonstration of a Sizeable Nonclassical CH···G Hydrogen Bond in Cyclohexane Derivatives: Stabilization
Kyle M Lambert1, Zachary D Stempel1, Kenneth B Wiberg2
1Department of Chemistry, University of Connecticut , 55 North Eagleville Road, Storrs, Connecticut 06269-3060, United States.
Abstract:
Base-catalyzed equilibration of anancomeric cyanocyclohexanes demonstrates that replacement of cis-3,5-dimethyl holding groups with electron-withdrawing CF3 groups dramatically increases the proportion of the axial cyano isomer present at equilibrium. The CF3 groups exert an effect on the conformational energy of the cyano group worth about 0.6 kcal/mol. A nonclassical hydrogen bond between the axial CN group and the syn-axial hydrogens is a major contributor to the axial stability of the group.
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