Radically different antioxidants: thermally generated carbon-centered radicals as chain-breaking antioxidants

Mathieu Frenette; Patricia D MacLean; L Ross C Barclay; Juan C Scaiano

doi:10.1021/ja066870j

Radically different antioxidants: thermally generated carbon-centered radicals as chain-breaking antioxidants

J Am Chem Soc. 2006 Dec 27;128(51):16432-3. doi: 10.1021/ja066870j.

Authors

Mathieu Frenette¹, Patricia D MacLean, L Ross C Barclay, Juan C Scaiano

Affiliation

¹ Department of Chemistry, University of Ottawa, Ottawa, Ontario K1N 6N5, Canada.

PMID: 17177355
DOI: 10.1021/ja066870j

Abstract

A new class of thermally activated chain-breaking antioxidants is presented. Dimers of persistent carbon-centered radicals are able to inhibit the autoxidation of cumene and styrene with better rate constants than the commercial antioxidant Irganox HP-136 and 3,5-di-tert-butyl-4-hydroxyanisole. A dramatic increase in antioxidant activity is observed with increasing temperature as more dimers dissociate to their corresponding persistent radicals.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antioxidants / chemistry*
Benzene Derivatives / antagonists & inhibitors
Benzene Derivatives / chemistry
Carbon / chemistry*
Dimerization
Free Radicals / chemistry
Lactones / chemistry*
Molecular Structure
Oxidation-Reduction
Styrene / antagonists & inhibitors
Styrene / chemistry
Time Factors

Substances

Antioxidants
Benzene Derivatives
Free Radicals
HP-136
Lactones
Styrene
Carbon
cumene