The three electron π-bond in hydrazyl radical. An ab initio scf-mo investigation of torsional and inversional stereomutation

M. Raban; K. Aviram; D. Kost

doi:10.1016/S0040-4039(00)89198-4

The three electron π-bond in hydrazyl radical. An ab initio scf-mo investigation of torsional and inversional stereomutation

M. Raban, K. Aviram, D. Kost

Department of Chemistry

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8 Scopus citations

Abstract

The mechanism for stereomutation in hydrazyl radical is analyzed in terms of simple perturbational molecular orbital theory and SCF-MO calculations. The ground state is planar due to three electron π-stabilization. The torsional barrier (29 kcal/mol) is approximately half that of the hydrazyl cation. Torsion and planar inversion have barriers comparable in magnitude, resulting in a mechanism intermediate between these two extremes.

Original language	English
Pages (from-to)	3591-3594
Number of pages	4
Journal	Tetrahedron Letters
Volume	26
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(00)89198-4
State	Published - 1 Jan 1985

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)89198-4

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title = "The three electron π-bond in hydrazyl radical. An ab initio scf-mo investigation of torsional and inversional stereomutation",

abstract = "The mechanism for stereomutation in hydrazyl radical is analyzed in terms of simple perturbational molecular orbital theory and SCF-MO calculations. The ground state is planar due to three electron π-stabilization. The torsional barrier (29 kcal/mol) is approximately half that of the hydrazyl cation. Torsion and planar inversion have barriers comparable in magnitude, resulting in a mechanism intermediate between these two extremes.",

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AU - Aviram, K.

AU - Kost, D.

PY - 1985/1/1

Y1 - 1985/1/1

N2 - The mechanism for stereomutation in hydrazyl radical is analyzed in terms of simple perturbational molecular orbital theory and SCF-MO calculations. The ground state is planar due to three electron π-stabilization. The torsional barrier (29 kcal/mol) is approximately half that of the hydrazyl cation. Torsion and planar inversion have barriers comparable in magnitude, resulting in a mechanism intermediate between these two extremes.

AB - The mechanism for stereomutation in hydrazyl radical is analyzed in terms of simple perturbational molecular orbital theory and SCF-MO calculations. The ground state is planar due to three electron π-stabilization. The torsional barrier (29 kcal/mol) is approximately half that of the hydrazyl cation. Torsion and planar inversion have barriers comparable in magnitude, resulting in a mechanism intermediate between these two extremes.

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DO - 10.1016/S0040-4039(00)89198-4

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The three electron π-bond in hydrazyl radical. An ab initio scf-mo investigation of torsional and inversional stereomutation

Abstract

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