Electron Apportionment in Cleavage of Radical Anions. 1. Nitro-Substituted Benzyl Phenyl Ethers

Przemyslaw Maslak; Robert D. Guthrie

doi:10.1021/ja00270a021

Electron Apportionment in Cleavage of Radical Anions. 1. Nitro-Substituted Benzyl Phenyl Ethers

Przemyslaw Maslak, Robert D. Guthrie

Chemistry

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83 Scopus citations

Abstract

The radical anions of 4-nitrobenzyl phenyl ethers undergo cleavage at least 10⁴times faster than the radical anions of corresponding 4-nitrophenyl benzyl ethers despite a perceived thermodynamic advantage for the latter set of reactions. It is suggested that this result reflects a kinetic advantage for cleavage reactions which take place with regioconservation of spin density.

Original language	English (US)
Pages (from-to)	2628-2636
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	108
Issue number	10
DOIs	https://doi.org/10.1021/ja00270a021
State	Published - 1986

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00270a021

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title = "Electron Apportionment in Cleavage of Radical Anions. 1. Nitro-Substituted Benzyl Phenyl Ethers",

abstract = "The radical anions of 4-nitrobenzyl phenyl ethers undergo cleavage at least 104times faster than the radical anions of corresponding 4-nitrophenyl benzyl ethers despite a perceived thermodynamic advantage for the latter set of reactions. It is suggested that this result reflects a kinetic advantage for cleavage reactions which take place with regioconservation of spin density.",

author = "Przemyslaw Maslak and Guthrie, {Robert D.}",

year = "1986",

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T1 - Electron Apportionment in Cleavage of Radical Anions. 1. Nitro-Substituted Benzyl Phenyl Ethers

AU - Maslak, Przemyslaw

AU - Guthrie, Robert D.

PY - 1986

Y1 - 1986

N2 - The radical anions of 4-nitrobenzyl phenyl ethers undergo cleavage at least 104times faster than the radical anions of corresponding 4-nitrophenyl benzyl ethers despite a perceived thermodynamic advantage for the latter set of reactions. It is suggested that this result reflects a kinetic advantage for cleavage reactions which take place with regioconservation of spin density.

AB - The radical anions of 4-nitrobenzyl phenyl ethers undergo cleavage at least 104times faster than the radical anions of corresponding 4-nitrophenyl benzyl ethers despite a perceived thermodynamic advantage for the latter set of reactions. It is suggested that this result reflects a kinetic advantage for cleavage reactions which take place with regioconservation of spin density.

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M3 - Article

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JF - Journal of the American Chemical Society

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ER -

Electron Apportionment in Cleavage of Radical Anions. 1. Nitro-Substituted Benzyl Phenyl Ethers

Abstract

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