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

Moynihan, Humphrey A.; Hayes, John A.; Eccles, Kevin S.; Coles, Simon J.; Lawrence, Simon E.

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

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Files

HAM_HydrogenAV2013.pdf(957.42 KB)

Accepted Version

Date

2013-06

Authors

Moynihan, Humphrey A.

Hayes, John A.

Eccles, Kevin S.

Coles, Simon J.

Lawrence, Simon E.

Publisher

Elsevier

Published Version

10.1016/j.carres.2013.03.024

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.

Keywords

Glucose , Cellobiose , Primary amides , Crystal engineering

Citation

MOYNIHAN, H. A., HAYES, J. A., ECCLES, K. S., COLES, S. J. & LAWRENCE, S. E. 2013. Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose. Carbohydrate Research, 374, 29-39. http://dx.doi.org/10.1016/j.carres.2013.03.024