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- Title
Substituent Effects in Chain‐Breaking Aryltellurophenol Antioxidants.
- Authors
Poon, Jia‐fei; Yan, Jiajie; Donau, Carsten; Engman, Lars; Jorner, Kjell; Ottosson, Henrik; Singh, Vijay P.; Gates, Paul J.
- Abstract
Abstract: 2‐Aryltellurophenols substituted in the aryltelluro or phenolic parts of the molecule were prepared by lithiation of the corresponding tetrahydropyran‐protected 2‐bromophenol, followed by reaction with a suitable diaryl ditelluride then deprotection. In a two‐phase system containing <italic>N</italic>‐acetylcysteine as a co‐antioxidant in the aqueous phase, all of the compounds quenched lipid peroxyl radicals more efficiently than α‐tocopherol, with three to five‐fold longer inhibition times. Thus, these compounds offer better and longer‐lasting antioxidant protection than recently prepared alkyltellurophenols. Compounds with electron‐donating <italic>para</italic> substituents in the aryltelluro or phenolic part of the molecule showed the best results. The mechanism for quenching peroxyl radicals was considered and discussed with respect to the calculated O−H bond‐dissociation energies, deuterium‐labelling experiments and studies of thiol consumption in the aqueous phase.
- Subjects
ANTIOXIDANTS; HAMMETT equation; CURTIN-Hammett principle; NUCLEAR magnetic resonance spectroscopy; PHENOL analysis
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 14, p3520
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201704811