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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/148532ed27fc7-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 (2.8 MB)
Restricted Access
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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× 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 |
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| 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 | |||||
