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

^*Corresponding author for this work

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

23 Scopus citations

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

Funding

Work supported by DGA-PUCE Grant D29101 and FONDECYT Grant 1080184.

Funders	Funder number
PUCE-DGA	D29101
Fondo Nacional de Desarrollo Científico, Tecnológico y de Innovación Tecnológica	1080184

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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.

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AU - Pilaquinga, F.

AU - Fuentealba, P.

PY - 2008/7/20

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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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