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A Carbohydrate- Anion Recognition System in Aprotic Solvents
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2014 (English)In: Chemistry - An Asian Journal, ISSN 1861-4728, E-ISSN 1861-471X, Vol. 9, no 5, 1298-1304 p.Article in journal (Refereed) Published
Abstract [en]

A carbohydrate-anion recognition system in nonpolar solvents is reported, in which complexes form at the B-faces of -D-pyranosides with H1-, H3-, and H5-cis patterns similar to carbohydrate- interactions. The complexation effect was evaluated for a range of carbohydrate structures; it resulted in either 1:1 carbohydrate-anion complexes, or 1:2 complex formation depending on the protection pattern of the carbohydrate. The interaction was also evaluated with different anions and solvents. In both cases it resulted in significant binding differences. The results indicate that complexation originates from van der Waals interactions or weak CHA(-) hydrogen bonds between the binding partners and is related to electron-withdrawing groups of the carbohydrates as well as increased hydrogen-bond-accepting capability of the anions.

Place, publisher, year, edition, pages
2014. Vol. 9, no 5, 1298-1304 p.
Keyword [en]
anions, carbohydrates, molecular recognition, pi interactions, supramolecular chemistry
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-145807DOI: 10.1002/asia.201301617ISI: 000334779000014Scopus ID: 2-s2.0-84899458074OAI: oai:DiVA.org:kth-145807DiVA: diva2:721535
Funder
Swedish Research Council
Note

QC 20140604

Available from: 2014-06-04 Created: 2014-06-02 Last updated: 2017-12-05Bibliographically approved

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