Cyclic vs. acyclic allylic hydrogen abstraction: An entropy motivated process?

Gadi Rothenberg; Yoel Sasson

doi:10.1016/S0040-4020(98)00215-4

Cyclic vs. acyclic allylic hydrogen abstraction: An entropy motivated process?

Gadi Rothenberg^*
, Yoel Sasson

^*Corresponding author for this work

Institute of Chemistry

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

10 Scopus citations

Abstract

Optimized geometries for the reactants, products, and transition structures of cyclic and acyclic allylic hydrogen abstractions by tert- butoxy radicals were obtained by semiempirical methods. In the four model cases studied the transition structures were all early and linear, with large imaginary frequencies, around 2000 cm^-1. Enthalpic effects, rather than entropic ones, are deemed as responsible for the 'cyclic activation' of allylic hydrogens towards free-radicals.

Original language	English
Pages (from-to)	5417-5422
Number of pages	6
Journal	Tetrahedron
Volume	54
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4020(98)00215-4
State	Published - 14 May 1998

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title = "Cyclic vs. acyclic allylic hydrogen abstraction: An entropy motivated process?",

abstract = "Optimized geometries for the reactants, products, and transition structures of cyclic and acyclic allylic hydrogen abstractions by tert- butoxy radicals were obtained by semiempirical methods. In the four model cases studied the transition structures were all early and linear, with large imaginary frequencies, around 2000 cm-1. Enthalpic effects, rather than entropic ones, are deemed as responsible for the 'cyclic activation' of allylic hydrogens towards free-radicals.",

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AU - Sasson, Yoel

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Y1 - 1998/5/14

N2 - Optimized geometries for the reactants, products, and transition structures of cyclic and acyclic allylic hydrogen abstractions by tert- butoxy radicals were obtained by semiempirical methods. In the four model cases studied the transition structures were all early and linear, with large imaginary frequencies, around 2000 cm-1. Enthalpic effects, rather than entropic ones, are deemed as responsible for the 'cyclic activation' of allylic hydrogens towards free-radicals.

AB - Optimized geometries for the reactants, products, and transition structures of cyclic and acyclic allylic hydrogen abstractions by tert- butoxy radicals were obtained by semiempirical methods. In the four model cases studied the transition structures were all early and linear, with large imaginary frequencies, around 2000 cm-1. Enthalpic effects, rather than entropic ones, are deemed as responsible for the 'cyclic activation' of allylic hydrogens towards free-radicals.

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Cyclic vs. acyclic allylic hydrogen abstraction: An entropy motivated process?

Abstract

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