The single-electron shift as a basis of organic reactivity

Addy Pross; David M. Chipman

doi:10.1016/0891-5849(87)90039-6

The single-electron shift as a basis of organic reactivity

Addy Pross, David M. Chipman

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

6 Scopus citations

Abstract

The configuration mixing (CM) model is applied to the building of a simple reaction profile for nucleophilic addition to a carbonyl group. The analysis leads us to conclude that essentially all the so-called polar reaction pathways in organic chemistry are single-electron shift processes and intimately related to the class of electron transfer (ET) reactions. The implication of this finding to a variety of organic reactions, including oxidation-reduction of the NADH/NAD⁺ coenzyme couple, is discussed.

Original language	English
Pages (from-to)	55-64
Number of pages	10
Journal	Free Radical Biology and Medicine
Volume	3
Issue number	1
DOIs	https://doi.org/10.1016/0891-5849(87)90039-6
State	Published - 1 Jan 1987

Keywords

Configuration mixing
Electron transfer
Hydride transfer
Nucleophilic addition
Single-electron shift

ASJC Scopus subject areas

Biochemistry
Physiology (medical)

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10.1016/0891-5849(87)90039-6

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AB - The configuration mixing (CM) model is applied to the building of a simple reaction profile for nucleophilic addition to a carbonyl group. The analysis leads us to conclude that essentially all the so-called polar reaction pathways in organic chemistry are single-electron shift processes and intimately related to the class of electron transfer (ET) reactions. The implication of this finding to a variety of organic reactions, including oxidation-reduction of the NADH/NAD+ coenzyme couple, is discussed.

KW - Configuration mixing

KW - Electron transfer

KW - Hydride transfer

KW - Nucleophilic addition

KW - Single-electron shift

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The single-electron shift as a basis of organic reactivity

Abstract

Keywords

ASJC Scopus subject areas

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