Bifurcated hydrogen bond in rare sugar by computational study

• Published in: Molecular Crystals and Liquid Crystals Vol. 646; no. 1; pp. 31 - 40
• Main Authors: Kotena, Zahrabatoul Mosapour, Mohamad, Saharuddin Bin
• Format: Journal Article
• Language: English
• Published: Philadelphia Taylor & Francis 24.03.2017; Taylor & Francis Ltd
• Subjects: bifurcated hydrogen bond; Bifurcations; Chemical bonds; Density functional theory; Glucose; Hydrogen; Hydrogen bonds; hydroxyl group; Hydroxyl groups; Idose and glucose sugars; Monosaccharides; Sugar
• ISSN: 1542-1406; 1563-5287; 1527-1943
• DOI: 10.1080/15421406.2017.1283920

The monosaccharides such as D-β-glucose and D-β-idose sugars differ on the hydroxyl group's orientation at the C2-C4 positions. Hydroxyl groups such as OH2, OH3, and OH4 in β-idose are axial, while all (OHs) groups in β-glucose are equatorial. The density functional theory based on the B3LYP/6-31G * level results show that β-glucose is more stable than in β-idose. AIM analysis indicates the existence of intra-molecular hydrogen bond so that β-glucose displays regular intra-molecular hydrogen bond, while β-idose displays bifurcated acceptor intra-molecular hydrogen bond. The NBO analysis has been confirmed that the formation of intra-molecular hydrogen bonds in these two sugars.