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Org Lett. 2003 Feb 20;5(4):387-90.

Role of hyperconjugation in determining carbon-oxygen bond dissociation enthalpies in alkylperoxyl radicals.

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1
Department of Chemistry and Center for Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235, USA.

Abstract

[reaction: see text] Theoretical calculations of carbon-oxygen bond dissociation enthalpies in substituted methylperoxyl radicals (YCH(2)OO*) reveal that bond strengths are not governed solely by the stability of YCH2* radicals but are largely affected by hyperconjugation when Y is electron-donating or conjugating. In many cases, this hyperconjugative effect is greater than stabilization of the methyl radical by Y. All electron-withdrawing Y exert small destabilizing effects via inductive withdrawal of electrons from the polarized C-OO* bond.

PMID:
12583725
DOI:
10.1021/ol027094x
[Indexed for MEDLINE]
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