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.