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Issue 22, 2003
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Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium

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Abstract

Electron-transfer reduction of molecular oxygen (O2) by the phenolate anion (1) of a vitamin E model, 2,2,5,7,8-pentamethylchroman-6-ol (1H), occurred to produce superoxide anion, which could be directly detected by a low-temperature EPR measurement. The rate of electron transfer from 1 to O2 was relatively slow, since this process is energetically unfavourable. The one-electron oxidation potential of 1 determined by cyclic voltammetric measurements is sufficiently negative to reduce 2,2-bis(4-tert-octylphenyl)-1-picrylhydrazyl radical (DOPPH˙) to the corresponding one-electron reduced anion, DOPPH, suggesting that 1 can also act as an efficient radical scavenger.

Graphical abstract: Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium

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Publication details

The article was received on 18 Jun 2003, accepted on 23 Sep 2003 and first published on 13 Oct 2003


Article type: Paper
DOI: 10.1039/B306758K
Citation: Org. Biomol. Chem., 2003,1, 4085-4088
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    Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium

    I. Nakanishi, K. Miyazaki, T. Shimada, Y. Iizuka, K. Inami, M. Mochizuki, S. Urano, H. Okuda, T. Ozawa, S. Fukuzumi, N. Ikota and K. Fukuhara, Org. Biomol. Chem., 2003, 1, 4085
    DOI: 10.1039/B306758K

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