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

Abdel-Monem M. Rawashdeh; Arumugam Thangavel; Chariklia Sotiriou-Leventis; Nicholas Leventis

doi:10.1021/ol800021r

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

Abdel-Monem M. Rawashdeh
, Arumugam Thangavel
, Chariklia Sotiriou-Leventis
, Nicholas Leventis

Missouri University of Science and Technology

Missouri University of Science and Technology

Research output: Contribution to journal › Article › peer-review

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.

Original language	American English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/ol800021r
State	Published - Jan 1 2007

Disciplines

Chemistry

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https://doi.org/10.1021/ol800021r

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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.",

author = "Rawashdeh, \{Abdel-Monem M.\} and Arumugam Thangavel and Chariklia Sotiriou-Leventis and Nicholas Leventis",

year = "2007",

month = jan,

day = "1",

doi = "10.1021/ol800021r",

language = "American English",

journal = "Organic Letters",

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TY - JOUR

T1 - Control of the Ketone to Gem-diol Equilibrium by Host-guest Interactions

AU - Rawashdeh, Abdel-Monem M.

AU - Thangavel, Arumugam

AU - Sotiriou-Leventis, Chariklia

AU - Leventis, Nicholas

PY - 2007/1/1

Y1 - 2007/1/1

N2 - 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.

AB - 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.

UR - https://scholarsmine.mst.edu/chem_facwork/92

UR - https://doi.org/10.1021/ol800021r

U2 - 10.1021/ol800021r

DO - 10.1021/ol800021r

M3 - Article

SN - 1523-7052

JO - Organic Letters

JF - Organic Letters

ER -

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

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