Supramolecular stacking motifs in the solid state of amide and triazole derivatives of cellobiose

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Supramolecular stacking motifs in the solid state of amide and triazole derivatives of cellobiose

Hayes, John A.; Eccles, Kevin S.; Coles, Simon J.; Lawrence, Simon E.; Moynihan, Humphrey A.
Date: 2014-03
Copyright: Copyright © 2014 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 388, 31 March 2014, Pages 67–72] DOI http://dx.doi.org/10.1016/j.carres.2014.02.011
Related: http://www.sciencedirect.com/science/article/pii/S000862151400072X
Citation: HAYES, J. A., ECCLES, K. S., COLES, S. J., LAWRENCE, S. E. & MOYNIHAN, H. A. 2014. Supramolecular stacking motifs in the solid state of amide and triazole derivatives of cellobiose. Carbohydrate Research, 388, 67-72. http://dx.doi.org/10.1016/j.carres.2014.02.011
Published Version: 10.1016/j.carres.2014.02.011

Abstract:

1-Acetamido-1-deoxy-(4-O-β-d-glucopyranosyl-β-d-glucopyranose) (5) and 1-deoxy-1-(4-phenyl-1,2,3-triazolyl)-(4-O-β-d-glucopyranosyl-β-d-glucopyranose) (7) were synthesised from 1-azido-1-deoxy-(4-O-β-d-glucopyranosyl-β-d-glucopyranose) (2) and crystallised as dihydrates. Crystal structural analysis of 5·2H2O displayed an acetamide C(4) chain and stacked cellobiose residues. The structure of 7·2H2O featured π–π stacking and stacking of the cellobiose residues

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