Multinuclear magnetic resonance and molecular mechanics studies on the conformations and the dynamic behaviors of α‐alkyl‐substituted o ‐methoxybenzyl alcohols

Abstract

The conformations and the dynamic behaviors of α-monoalkyl- and α,α-dialkyl-o-methoxybenzyl alcohols are discussed on the basis of their 1H, 13C and 17O NMR spectra and MM3 calculations. The conformations of α-monoalkyl derivatives are shown to be different from those of α,α-dialkyl derivatives and unfavorable to form intramolecular OH · · · O hydrogen bonds. The trends of substituent effects on the restricted rotation about the Cipso—Cα bond could be reproduced fairly well by MM3 calculations. © 1997 John Wiley & Sons, Ltd.