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

Gadi Rothenberg*, Yoel Sasson

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)5417-5422
Number of pages6
JournalTetrahedron
Volume54
Issue number20
DOIs
StatePublished - 14 May 1998

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