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Issue 33, 2016
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Aluminium ion-promoted radical-scavenging reaction of methylated hydroquinone derivatives

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Abstract

The effect of the aluminium ion (Al3+) on the scavenging reaction of a 2,2-diphenyl-1-picrylhydrazyl radical (DPPH˙), as a reactivity model of reactive oxygen species, with hydroquinone (QH2) and its methylated derivatives (MenQH2, n = 1–4) was investigated using stopped-flow and electrochemical techniques in a hydroalcoholic medium. The second-order rate constants (k) for the DPPH˙-scavenging reaction of the hydroquinones increased with the increasing number of methyl substituents. Upon addition of Al3+, the k values significantly increased depending on the concentration of Al3+. Such an accelerating effect of Al3+ on the DPPH˙-scavenging rates of the hydroquinones results from the remarkable positive shift of the one-electron reduction potential (Ered) of DPPH˙ in the presence of Al3+. These results demonstrate that Al3+, a strong Lewis acid, can act as a radical-scavenging promoter by stabilising the one-electron reduced species of the radical, although Al3+ is reported not only to act as a pro-oxidant but also to strongly interact with biomolecules, showing toxicities.

Graphical abstract: Aluminium ion-promoted radical-scavenging reaction of methylated hydroquinone derivatives

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Publication details

The article was received on 11 Jul 2016, accepted on 29 Jul 2016 and first published on 29 Jul 2016


Article type: Paper
DOI: 10.1039/C6OB01470D
Citation: Org. Biomol. Chem., 2016,14, 7956-7961
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    Aluminium ion-promoted radical-scavenging reaction of methylated hydroquinone derivatives

    I. Nakanishi, K. Ohkubo, Y. Ogawa, K. Matsumoto, T. Ozawa and S. Fukuzumi, Org. Biomol. Chem., 2016, 14, 7956
    DOI: 10.1039/C6OB01470D

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