Relationship between the electrophilicity and σp Hammett constant in Baeyer-Villiger reactions

L. Meneses; A. Araya; F. Pilaquinga; P. Fuentealba

doi:10.1016/j.cplett.2008.05.044

Relationship between the electrophilicity and σ_p Hammett constant in Baeyer-Villiger reactions

L. Meneses, A. Araya, F. Pilaquinga, P. Fuentealba

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Abstract

The Baeyer-Villiger oxidation of some aldehydes and ketones has been revised by using the electrophilicity as a descriptor of reactivity. The global electrophilicity index evaluated at the ground state of a series of aromatic aldehydes and ketones shows a linear relationship with the σ_p Hammett substituent constants. The theoretical scale correctly accounts for the electrophilic activation/deactivation effects promoted by electron withdrawing and electron releasing substituents in these molecules.

Original language	English
Pages (from-to)	27-30
Number of pages	4
Journal	Chemical Physics Letters
Volume	460
Issue number	1-3
DOIs	https://doi.org/10.1016/j.cplett.2008.05.044
State	Published - 20 Jul 2008

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10.1016/j.cplett.2008.05.044

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abstract = "The Baeyer-Villiger oxidation of some aldehydes and ketones has been revised by using the electrophilicity as a descriptor of reactivity. The global electrophilicity index evaluated at the ground state of a series of aromatic aldehydes and ketones shows a linear relationship with the σp Hammett substituent constants. The theoretical scale correctly accounts for the electrophilic activation/deactivation effects promoted by electron withdrawing and electron releasing substituents in these molecules.",

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AU - Meneses, L.

AU - Araya, A.

AU - Pilaquinga, F.

AU - Fuentealba, P.

PY - 2008/7/20

Y1 - 2008/7/20

N2 - The Baeyer-Villiger oxidation of some aldehydes and ketones has been revised by using the electrophilicity as a descriptor of reactivity. The global electrophilicity index evaluated at the ground state of a series of aromatic aldehydes and ketones shows a linear relationship with the σp Hammett substituent constants. The theoretical scale correctly accounts for the electrophilic activation/deactivation effects promoted by electron withdrawing and electron releasing substituents in these molecules.

AB - The Baeyer-Villiger oxidation of some aldehydes and ketones has been revised by using the electrophilicity as a descriptor of reactivity. The global electrophilicity index evaluated at the ground state of a series of aromatic aldehydes and ketones shows a linear relationship with the σp Hammett substituent constants. The theoretical scale correctly accounts for the electrophilic activation/deactivation effects promoted by electron withdrawing and electron releasing substituents in these molecules.

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Relationship between the electrophilicity and σ_p Hammett constant in Baeyer-Villiger reactions

Abstract

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