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Alkyltelluro Substitution Improves the Radical-Trapping Capacity of Aromatic Amines
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.ORCID iD: 0000-0002-5568-7415
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
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2016 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 36, 12891-12903 p.Article in journal (Refereed) Published
Abstract [en]

The synthesis of a variety of aromatic amines carrying an ortho-alkyltelluro group is described. The new antioxidants quenched lipidperoxyl radicals much more efficiently than α-tocopherol and were regenerable by aqueous-phase N-acetylcysteine in a two-phase peroxidation system. The inhibition time for diaryl amine 9 b was four-fold longer than recorded with α-tocopherol. Thiol consumption in the aqueous phase was found to correlate inversely to the inhibition time and the availability of thiol is the limiting factor for the duration of antioxidant protection. The proposed mechanism for quenching of peroxyl radicals involves O-atom transfer from peroxyl to Te followed by H-atom transfer from amine to alkoxyl radical in a solvent cage.

Place, publisher, year, edition, pages
2016. Vol. 22, no 36, 12891-12903 p.
National Category
Organic Chemistry
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URN: urn:nbn:se:uu:diva-302460DOI: 10.1002/chem.201602377PubMedID: 27484352OAI: oai:DiVA.org:uu-302460DiVA: diva2:957710
Available from: 2016-09-04 Created: 2016-09-04 Last updated: 2016-09-09Bibliographically approved
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Poon, Jia-FeiYan, JiajieSingh, Vijay PEngman, Lars
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