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Issue 4, 2005
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Electron-transfer mechanism in radical-scavenging reactions by a vitamin E model in a protic medium

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Abstract

The scavenging reaction of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH˙) or galvinoxyl radical (GO˙) by a vitamin E model, 2,2,5,7,8-pentamethylchroman-6-ol (1H), was significantly accelerated by the presence of Mg(ClO4)2 in de-aerated methanol (MeOH). Such an acceleration indicates that the radical-scavenging reaction of 1H in MeOH proceeds via an electron transfer from 1H to the radical, followed by a proton transfer, rather than the one-step hydrogen atom transfer which has been observed in acetonitrile (MeCN). A significant negative shift of the one-electron oxidation potential of 1H in MeOH (0.63 V vs. SCE), due to strong solvation as compared to that in MeCN (0.97 V vs. SCE), may result in change of the radical-scavenging mechanisms between protic and aprotic media.

Graphical abstract: Electron-transfer mechanism in radical-scavenging reactions by a vitamin E model in a protic medium

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Publication details

The article was received on 11 Nov 2004, accepted on 29 Nov 2004 and first published on 11 Jan 2005


Article type: Paper
DOI: 10.1039/B416572A
Citation: Org. Biomol. Chem., 2005,3, 626-629
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    Electron-transfer mechanism in radical-scavenging reactions by a vitamin E model in a protic medium

    I. Nakanishi, T. Kawashima, K. Ohkubo, H. Kanazawa, K. Inami, M. Mochizuki, K. Fukuhara, H. Okuda, T. Ozawa, S. Itoh, S. Fukuzumi and N. Ikota, Org. Biomol. Chem., 2005, 3, 626
    DOI: 10.1039/B416572A

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