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

Author

Abdel-Monem M. Rawashdeh
Arumugam Thangavel
Chariklia Sotiriou-Leventis, Missouri University of Science and TechnologyFollow
Nicholas Leventis, Missouri University of Science and TechnologyFollow

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.

Recommended Citation

A. M. Rawashdeh et al., "Control of the Ketone to Gem-diol Equilibrium by Host-guest Interactions," Organic Letters, American Chemical Society (ACS), Jan 2007.

The definitive version is available at https://doi.org/10.1021/ol800021r

Department(s)

Chemistry

Sponsor(s)

University of Missouri Research Board

International Standard Serial Number (ISSN)

1523-7060

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

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

Publication Date

01 Jan 2007