The Conformations of Several Aliphatic Alcohols. The General Occurrence of the Attractive Alkyl/Phenyl Interaction

Abstract

Abstract The conformation has been studied, by means of NMR spectroscopy, for diastereoisomeric pairs of a series of alcohols having the following general structure: CH_3CH(C_6H_5)CH(OH)–R where R is a methyl, ethyl, isopropyl, or a t-butyl group. It has been demonstrated that the alkyl group (R) is oriented close to the phenyl group in the most preferred conformations; this conclusion is essentially in accord with the results obtained for the structurally related sulfoxides. The general occurrence of an attractive interaction (the CH/π interaction) has, therefore, been suggested between an alkyl and a phenyl group.