NDLI: 3-Pyridinols and 5-pyrimidinols: Tailor-made for use in synergistic radical-trapping co-antioxidant systems

Content Provider	PubMed Central
Author	Luca, Valgimigli Bartolomei, Daniele Riccardo, Amorati Haidasz, Evan Hanthorn, Jason J. Nara, Susheel J. Brinkhorst, Johan Pratt, Derek A.
Editor	Stephenson, Corey
Copyright Year	2013
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 reactive phenols to regenerate them from their corresponding aryloxyl radicals. The present investigations were carried out in chlorobenzene and acetonitrile in order to provide some insight into the medium dependence of the synergism and the results, considered with some from our earlier work, prompt a revision of the H-bonding basicity value of acetonitrile to β2 H of 0.39. Overall, the thermodynamic and kinetic data presented here enable the design of co-antioxidant systems comprising lower loadings of the more expensive 3-pyridinol/5-pyrimidinol antioxidants and higher loadings of the less expensive phenolic antioxidants, but which are equally efficacious as the 3-pyridinol/5-pyrimidinol antioxidants alone at higher loadings.
Related Links	http://dx.doi.org/10.3762/bjoc.9.313
Ending Page	2792
Page Count	12
Starting Page	2781
File Format	PDF
ISSN	18605397
e-ISSN	18605397
Journal	Beilstein Journal of Organic Chemistry
Volume Number	9
Language	English
Publisher	Beilstein-Institut
Publisher Date	2013-12-01
Access Restriction	Open
Rights Holder	Beilstein-Institut
Subject Keyword	Organic Chemistry Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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