Experimental Demonstration of a Sizeable Nonclassical CH···G Hydrogen Bond in Cyclohexane Derivatives: Stabilization of an Axial Cyano Group.

Lambert, Kyle M; Stempel, Zachary D; Wiberg, Kenneth B; Bailey, William F

Lambert, Kyle M; Stempel, Zachary D; Wiberg, Kenneth B; Bailey, William F.

Afiliación

Lambert KM; Department of Chemistry, University of Connecticut , 55 North Eagleville Road, Storrs, Connecticut 06269-3060, United States.
Stempel ZD; Department of Chemistry, University of Connecticut , 55 North Eagleville Road, Storrs, Connecticut 06269-3060, United States.
Wiberg KB; Department of Chemistry, Yale University , 275 Prospect Street, New Haven, Connecticut 06520-8107, United States.
Bailey WF; Department of Chemistry, University of Connecticut , 55 North Eagleville Road, Storrs, Connecticut 06269-3060, United States.

Org Lett ; 19(23): 6408-6411, 2017 12 01.

Article en En | MEDLINE | ID: mdl-29144141

RESUMEN

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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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2017 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos

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