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

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Moynihan, Humphrey A.
Hayes, John A.
Eccles, Kevin S.
Coles, Simon J.
Lawrence, Simon E.
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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.
Glucose , Cellobiose , Primary amides , Crystal engineering
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
Copyright © 2013 Elsevier Ltd. All rights reserved. NOTICE: this is the author’s version of a work that was accepted for publication in Carbohydrate Research. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Carbohydrate Research, [Volume 374, 7 June 2013, Pages 29–39] DOI http://dx.doi.org/10.1016/j.carres.2013.03.024