Title

Control of the Ketone to Gem-diol Equilibrium by Host-guest Interactions

Abstract

In water, N-methyl-4-(p-substituted benzoyl)pyridinium cations, BP-X, exist in equilibrium with their hydrated forms (gem-diols), whose concentrations depend on the para substituent (-X). In the presence of cucurbit[7]uril (CB[7]), the benzoyl group shows a preference for the CB[7] cavity, and the ketone to gem-diol equilibrium is shifted toward the keto form, meaning that the stabilization realized through hydrophobic interactions of the benzoyl group in the CB[7] cavity exceeds the hydrogen-bonding stabilization of the gem-diols in the aqueous environment.

Department(s)

Chemistry

Sponsor(s)

University of Missouri Research Board

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2007 American Chemical Society (ACS), All rights reserved.


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