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Reactivities of 1,2-, 1,3-, and 1,4-dihydroxynaphthalenes toward electrogenerated superoxide in N,N-dimethylformamide through proton-coupled electron transfer

https://gifu-pu.repo.nii.ac.jp/records/14853
https://gifu-pu.repo.nii.ac.jp/records/14853
2ed27fc7-b2d5-41a6-87d3-e8c7edfe014e
名前 / ファイル ライセンス アクション
1-s2.0-S0013468622016243-main.pdf 1-s2.0-S0013468622016243-main (2.8 MB)
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Item type 一般雑誌記事 / Article(1)
公開日 2023-03-20
タイトル
タイトル Reactivities of 1,2-, 1,3-, and 1,4-dihydroxynaphthalenes toward electrogenerated superoxide in N,N-dimethylformamide through proton-coupled electron transfer
タイトル
タイトル Reactivities of 1,2-, 1,3-, and 1,4-dihydroxynaphthalenes toward electrogenerated superoxide in N,N-dimethylformamide through proton-coupled electron transfer
言語 en
言語
言語 eng
資源タイプ
資源タイプ識別子 http://purl.org/coar/resource_type/c_6501
資源タイプ article
著者 nakayama, tatsushi

× nakayama, tatsushi

WEKO 32440
CiNii ID N000638361

nakayama, tatsushi

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Uno, Bunji

× Uno, Bunji

WEKO 36618

Uno, Bunji

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抄録
内容記述タイプ Abstract
内容記述 We have carried out an electrochemical and theoretical study on the reactivity of 1,2-, 1,3-, and 1,4-dihydroxynaphthalenes (1nH2NQ, n = 2, 3, 4) toward electrogenerated superoxide radical anion (O2•−) in N,N-dimethylformamide. Cyclicvoltammetry and in situ electrolytic electron spin resonance measurements revealed that the quinone–hydroquinone π-conjugation plays an important role in a successful O2•− scavenging by 12H2NQ and 14H2NQ through proton-coupled electron transfer (PCET) reaction. The reactivities of 12H2NQ and 14H2NQ toward O2•− were mediated by the ortho- (catechol) or para-diphenol (hydroquinone) moieties, as experimentally confirmed in comparative analyses with catechol, hydroquinone, and 13H2NQ, aided by density functional theory (DFT) calculations. The electrochemical and DFT results suggested that a concerted PCET mechanism involving two-proton transfers and one-electron transfer proceeds, demonstrating a successful O2•− scavenging by 12H2NQ and 14H2NQ. Furthermore, a subsequent electron transfer between molecular dioxygen and product-naphthoquinone-radicals was observed, where O2•− was regenerated. The DFT analysis suggested that the spin distribution on the planar naphthalene ring embodies the superior kinetics of the PCET and the subsequent generation of O2•− from dioxygen demonstrated in the electrochemical results.
書誌情報 Electrochimica Acta
en : Electrochimica Acta

巻 436, p. 141467, 発行日 2022-11-01
出版者
出版者 Elsevier
ISSN
収録物識別子タイプ ISSN
収録物識別子 00134686
DOI
識別子タイプ DOI
関連識別子 10.1016/j.electacta.2022.141467
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