Intramolecular hydrogen bonds in monosaccharides in dimethyl sulfoxide solution

Abstract

By the use of the SIMPLE NMR method, strong intramolecular hydrogen bonds were found in the Me₂SO solutions of sugars having two syn-axial hydroxy groups, like the talopyranoses. Weaker hydrogen bonds were detected between hydroxy groups in a 1,3-arrangement when one was outside the ring but only weak, although numerous, hydrogen bonds were detected in solutions of other sugars and inositols.