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

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dc.contributor.authorMoynihan, Humphrey A.
dc.contributor.authorHayes, John A.
dc.contributor.authorEccles, Kevin S.
dc.contributor.authorColes, Simon J.
dc.contributor.authorLawrence, Simon E.
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2014-07-16T15:51:50Z
dc.date.available2014-07-16T15:51:50Z
dc.date.issued2013-06
dc.date.updated2014-06-18T09:12:06Z
dc.description.abstractA 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.en
dc.description.sponsorshipScience Foundation Ireland (07/SRC/B1158, 05/PICA/B802/EC07)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationMOYNIHAN, 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.2013.03.024en
dc.identifier.doi10.1016/j.carres.2013.03.024
dc.identifier.endpage39en
dc.identifier.issn0008-6215
dc.identifier.journaltitleCarbohydrate Researchen
dc.identifier.startpage29en
dc.identifier.urihttps://hdl.handle.net/10468/1588
dc.identifier.volume374en
dc.language.isoenen
dc.publisherElsevieren
dc.relation.urihttp://www.sciencedirect.com/science/article/pii/S0008621513001122
dc.rights© 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.2013.03.024en
dc.subjectGlucoseen
dc.subjectCellobioseen
dc.subjectPrimary amidesen
dc.subjectCrystal engineeringen
dc.titleHydrogen bonding in crystal forms of primary amide functionalized glucose and cellobioseen
dc.typeArticle (peer-reviewed)en
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