Cookies on this website
We use cookies to ensure that we give you the best experience on our website. If you click 'Continue' we'll assume that you are happy to receive all cookies and you won't see this message again. Click 'Find out more' for information on how to change your cookie settings.

We present direct investigations of the conformational preferences of sugars with a positively charged substituent at their anomeric centre, C-1, which display in solution, a preference for an equatorial conformation - an apparent reversal of the normal anomeric effect. The investigations focus on the protonated monosaccharide, d-xylopyranosyl imidazolium in its α and β forms, first probed in a range of different solvents through NMR measurements and then in the gas phase, free of solvent or counterion interactions, through infrared multiphoton dissociation spectroscopy. The results, when compared and discussed in the light of density functional theory, ab initio and natural bond orbital calculations, expose the possible origins of the reversed conformational preference and provide a better understanding of the factors controlling conformational choice. © The Royal Society of Chemistry 2012.

Original publication

DOI

10.1039/c2sc20341c

Type

Journal article

Journal

Chemical Science

Publication Date

01/01/2012

Volume

3

Pages

2307 - 2313