INTRAMOLECULAR HYDROGEN-BONDING IN PHENYL MONO-, DI-, AND TRI-O-METHYL-β-D-GLUCOPYRANOSIDES

Article abstract of DOI:10.1016/0008-6215(85)85145-4

I.r. spectroscopy has been used to obtain frequency shifts and integrated intensities of the hydroxyl-stretching vibration band for intramolecular hydrogen-bonding in 14 phenyl mono-, di-, and tri-O-methyl-β-D-glucopyranosides in solution in dilute carbon tetrachloride.Intramolecular hydrogen-bonding with characteristic differences were exhibited by these compounds and the results were interpreted in terms of the conformation of the hydroxyl group.For p-substituted phenyl 3,4,6-tri-O-methyl-β-D-glucopyranosides, the hydroxyl-stretching vibration bands were also measured for dilute solutions in carbon tetrachloride, and a linear relationship was found between the shift to a lower wave number and the Hammett ?_p constant.This shift was attributed to intramolecular hydrogen-bonding between HO-2 and O-1 which has a weaker proton-accepting ability than that of MeO-3.