Hydrogen bonding in crystal forms of primary amide functionalized glucose and cellobiose

Abstract

A glucoside and cellobioside of glycolamide were synthesised and the crystal chemistry of these compounds investigated. The amidoglucoside crystallised in the P 21 space group. The primary amide group participates in C(7) and C(17) chains also involving the pyranose oxygen and hydroxyl groups. The amidocellobioside crystallised as a methanol solvate in the P 21 space group. The amide N–H groups donate hydrogen bonds to oxygen atoms on the cellobiose units, while intramolecular hydrogen bonds give rise to S(7) and S(9) motifs in addition to a View the MathML sourceR33 (9) motif. A tetra-O-acetylglucoside derivative of thioglycolamide and its sulfoxide derivative were synthesised to examine the effect of protecting the glucopyranose hydroxyl groups. The thioglycolamido derivative, which crystallised in the P 212121 space group, featured amide N–H groups donating to the glucopyranose oxygen and an acetyloxy group. The sulfoxy derivative crystallised in the P 21 space group and featured the primary amide groups forming View the MathML sourceR23(8) motifs generating a 21 ladder.