Intrinsic barrier for protonation of radical anions

Esther Rozental; Shmaryahu Hoz

doi:10.1016/j.tet.2009.10.092

Intrinsic barrier for protonation of radical anions

Esther Rozental, Shmaryahu Hoz

Department of Chemistry

Bar-Ilan University

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

5 Scopus citations

Abstract

Ab initio calculations on radical anions show that, counterintuitively, protonation on the radicaloid carbon is favored. In the case of radical anions derived from acrylonitrile and acrylaldehyde, protonation on the heteroatom is less favored than protonation on the radicaloid carbon. However, in nitroethylene, the preferred protonation site is on the nitro oxygen in accordance with experimental observation.

Original language	English
Pages (from-to)	10945-10949
Number of pages	5
Journal	Tetrahedron
Volume	65
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2009.10.092
State	Published - 26 Dec 2009

Keywords

Intrinsic barrier
Marcus equation
Protonation
Radical anion

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10.1016/j.tet.2009.10.092

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abstract = "Ab initio calculations on radical anions show that, counterintuitively, protonation on the radicaloid carbon is favored. In the case of radical anions derived from acrylonitrile and acrylaldehyde, protonation on the heteroatom is less favored than protonation on the radicaloid carbon. However, in nitroethylene, the preferred protonation site is on the nitro oxygen in accordance with experimental observation.",

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AB - Ab initio calculations on radical anions show that, counterintuitively, protonation on the radicaloid carbon is favored. In the case of radical anions derived from acrylonitrile and acrylaldehyde, protonation on the heteroatom is less favored than protonation on the radicaloid carbon. However, in nitroethylene, the preferred protonation site is on the nitro oxygen in accordance with experimental observation.

KW - Intrinsic barrier

KW - Marcus equation

KW - Protonation

KW - Radical anion

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Intrinsic barrier for protonation of radical anions

Abstract

Keywords

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