Cooperativity and steric hindrance: Important factors in the binding of α-cyclodextrin with para-substituted aryl alkyl sulfides, sulfoxides and sulfones

Davies, Martin and Deary, Michael (1995) Cooperativity and steric hindrance: Important factors in the binding of α-cyclodextrin with para-substituted aryl alkyl sulfides, sulfoxides and sulfones. Journal of the Chemical Society, Perkin Transactions 2 (7). pp. 1287-1294. ISSN 1472-779X

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Official URL: http://dx.doi.org/ 10.1039/P29950001287

Abstract

Binding constants for 22 para-substituted aryl alkyl sulfides, sulfoxides and sulfones have been determined spectrophotometrically. It was found that the presence of sulfur containing substituents generally results in destabilisation of complex formation, and it is postulated that the angle of the sulfur bond in these compounds results in steric hindrance with the 5-H protons at the rear of the cyclodextrin cavity, causing it to be displaced from its optimal position or orientation. Additionally, the observation, for several sulfides, of cooperativity in the binding of a second molecule of cyclodextrin is discussed in terms of binding induced changes in electrical potential within the cyclodextrin cavity.

Item Type: Article
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: Becky Skoyles
Date Deposited: 28 Jan 2015 12:57
Last Modified: 10 Aug 2015 11:53
URI: http://nrl.northumbria.ac.uk/id/eprint/20218

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