Incorporation of Ring Nitrogens into Diphenylamine Antioxidants: Striking a Balance between Reactivity and Stability

The incorporation of nitrogen atoms into the aryl rings of conventional diphenylamine antioxidants enables the preparation of readily accessible, air-stable analogues, several of which have temperature-independent radical-trapping activities up to 200-fold greater than those of typical commercial di...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-05, Vol.134 (20), p.8306-8309
Main Authors: Hanthorn, Jason J, Valgimigli, Luca, Pratt, Derek A
Format: Article
Language:English
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Summary:The incorporation of nitrogen atoms into the aryl rings of conventional diphenylamine antioxidants enables the preparation of readily accessible, air-stable analogues, several of which have temperature-independent radical-trapping activities up to 200-fold greater than those of typical commercial diphenylamines. Amazingly, the nitrogen atoms raise the oxidation potentials of the amines without greatly changing their radical-trapping (H-atom transfer) reactivity.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja300086z