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Aluminium ion-promoted radical-scavenging reaction of methylated hydroquinone derivatives

Title
Aluminium ion-promoted radical-scavenging reaction of methylated hydroquinone derivatives
Authors
Nakanishi, IkuoOhkubo, KeiOgawa, YukihiroMatsumoto, Ken-ichiroOzawa, ToshihikoFukuzumi, Shunichi
Ewha Authors
Shunichi FukuzumiKei Okubo
SCOPUS Author ID
Shunichi Fukuzumiscopus; Kei Okuboscopus
Issue Date
2016
Journal Title
ORGANIC & BIOMOLECULAR CHEMISTRY
ISSN
1477-0520JCR Link1477-0539JCR Link
Citation
vol. 14, no. 33, pp. 7956 - 7961
Publisher
ROYAL SOC CHEMISTRY
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
The effect of the aluminium ion (Al3+) on the scavenging reaction of a 2,2-diphenyl-1-picrylhydrazyl radical (DPPH center dot), as a reactivity model of reactive oxygen species, with hydroquinone (QH(2)) and its methylated derivatives (Me(n)QH(2), n = 1-4) was investigated using stopped-flow and electrochemical techniques in a hydroalcoholic medium. The second-order rate constants (k) for the DPPH center dot-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 center dot-scavenging rates of the hydroquinones results from the remarkable positive shift of the one-electron reduction potential (E-red) of DPPH center dot 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.
DOI
10.1039/c6ob01470d
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자연과학대학 > 화학·나노과학전공 > Journal papers
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