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.

中文翻译：

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实验证明环己烷衍生物中相当大的非经典CH···G氢键：轴向氰基的稳定化

阴离子型氰基环己烷的碱催化平衡表明，用吸电子CF ₃基团取代顺式-3,5-二甲基保持基团可显着增加在平衡状态下存在的轴向氰基异构体的比例。CF ₃基团对价值约0.6kcal / mol的氰基的构象能产生影响。轴向CN组和S之间的非经典的氢键YN -axial氢是一个主要因素的组的轴向稳定性。