Substituent Effects in Chain-Breaking Aryltellurophenol Antioxidants

Jia Fei Poon, Jiajie Yan, Kjell Jorner, Henrik Ottosson, Carsten Donau, Vijay P. Singh, Paul J. Gates, Lars Engman*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

4 Citations (Scopus)
215 Downloads (Pure)

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 N-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 para 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.

Original languageEnglish
Pages (from-to)3520-3527
Number of pages8
JournalChemistry - A European Journal
Volume24
Issue number14
Early online date8 Feb 2018
DOIs
Publication statusPublished - 7 Mar 2018

Keywords

  • antioxidants
  • aryltellurophenols
  • lipid peroxidation
  • substituent effects
  • tellurium

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