Correlation of specific rotation with conformation. A new approach to the study of conformational equilibria

Abstract

The marked changes in optical rotation which occur on dissolving the methyl 2-deoxy-α-L-and 3-deoxy-β-L-erythro-pentopyranosides in a variety of solvents including chloroform, acetone, acetonitrile, pyridine, dimethylsulfoxide, and water were found by nuclear magnetic resonance to result almost exclusively from changes in conformational equilibria. The changes in rotation are in agreement with those expected from Brewster's rules.