Beilstein J. Org. Chem.2013,9, 2781–2792, doi:10.3762/bjoc.9.313
Pvt., Ottawa, Ontario, Canada K1N 6N5 10.3762/bjoc.9.313 Abstract The incorporation of nitrogen atoms into the aromatic ring of phenolic compounds has enabled the development of some of the most potent radical-trapping antioxidants ever reported. These compounds, 3-pyridinols and 5-pyrimidinols, have
stronger O–H bonds than equivalently substituted phenols, but possess similar reactivities toward autoxidation chain-carrying peroxyl radicals. These attributes suggest that 3-pyridinols and 5-pyrimidinols will be particularly effectiveco-antioxidants when used in combination with more common, but less
reactive, phenolic antioxidants such as 2,6-di-tert-butyl-4-methylphenol (BHT), which we demonstrate herein. The antioxidants function in a synergistic manner to inhibit autoxidation; taking advantage of the higher reactivity of the 3-pyridinols/5-pyrimidinols to trap peroxyl radicals and using the less
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Graphical Abstract
Scheme 1:
Autoxidation of an organic substrate RH.