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

Autor: Uzawa, Jun, Zushi, Shoji, Kodama, Yoshio, Fukuda, Yoshimasa, Nishihata, Ken, Umemura, Koshiro, Nishio, Motohiro, Hirota, Minoru
Zdroj: Bulletin of the Chemical Society of Japan; December 1980, Vol. 53 Issue: 12 p3623-3630, 8p
Abstrakt: 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)–Rwhere 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.
Databáze: Supplemental Index