Intramolecular Hydrogen Bonding in Dimethyl Sulfoxide Solutions of Glucose and Polyglucoses

Abstract

The downfield position (about 5r or lower) of certain hydroxyl proton resonance signals in the pmr spectra of glucose and polyglucoses in dimethyl sulfoxide solutions suggest the presence of intramolecular hydrogen bonds, namely, one involving the C-4 and C-6 group OH in glucose and, additionally in the polyglucoses, one between the C-3' OH and the ring oxygen in the adjacent glucopyranoside ring. The OH signals in the 5r region are in the proper ratio for the C-3' and C-4 OH protons in the polyglucoses examined. Absorption bands at 3500-3550 cm''in the ir spectra of methyl α-D- gtucopyranoside, cellobiose, and methyl cellobioside dissolved in DMSO and the absence of such an absorption in the methyl 6-deoxy-α-D-glucopyranoside spectrum provide further confirmation.

Keywords

Cellobiose methyl-β-cellobioise cellotetraose polyglucoses polysaccharides α-D-glucopyranosides methyl-6-deoxy- α-D-glucopyranoside glucoses monosaccharides. DMSO D2O d,-DMSO solvents nitrogen. Pressure concentration. OH proton resonance signals ir spectra pmr spectra hydrogen bonding solvent-bonding OH proton stretching fre quencies coupling constants chemical shifts. Intramoleuclar hydrogen bonding. Infrared spectroscopy pmr spectroscopy.

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