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Kinetics and Mechanism for the Scavenging Reaction of the 2,2-Diphenyl-1-picrylhydrazyl Radical by Synthetic Artepillin C Analogues
https://repo.qst.go.jp/records/48534
https://repo.qst.go.jp/records/4853417cadb76-6f7d-4553-a309-8f17551bcda1
| Item type | 学術雑誌論文 / Journal Article(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2018-02-20 | |||||
| タイトル | ||||||
| タイトル | Kinetics and Mechanism for the Scavenging Reaction of the 2,2-Diphenyl-1-picrylhydrazyl Radical by Synthetic Artepillin C Analogues | |||||
| 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 | journal article | |||||
| アクセス権 | ||||||
| アクセス権 | metadata only access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
| 著者 |
Kawashima, Tomonori
× Kawashima, Tomonori× Manda, Sushma× Uto, Yoshihiro× Ohkubo, Kei× Hori, Hitoshi× Matsumoto, Kenichiro× Fukuhara, Kiyoshi× Ikota, Nobuo× Fukuzumi, Shunichi× Ozawa, Toshihiko× Anzai, Kazunori× Nakanishi, Ikuo× 川島 知憲× Ｍａｎｄａ Ｓｕｓｈｍａ× 松本 謙一郎× 中西 郁夫 |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | The kinetics for the reaction of the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical with artepillin C, a prenylated phenylpropanoid found specifically in Brazilian propolis, and its analogues was examined in deaerated acetonitrile (MeCN) to shed light on the mechanism for the radical-scavenging reaction of phenolic antioxidants as well as on the structure-activity relationship. Among the examined analogues, a compound having a catechol moiety is found to have the largest second-order rate constant (k) for the DPPH radical-scavenging reaction. The deuterium kinetic isotope effect of 1.6 was observed for the DPPH radical-scavenging reaction of artepillin C in the presence of 0.13 M CD(3)OD or CH(3)OH in deaerated MeCN at 298 K. The log k values were found to be linearly correlated with calculated energy difference values (D(HT), HT = hydrogen transfer) between the artepillin C analogues and the corresponding phenoxyl radicals, while such a linear correlation cannot be observed between the log k values and calculated ionization potentials (IP), D(HT) - IP, or experimental one-electron oxidation potentials of the artepillin C analogues. These results together with a calculated structure of the transition state for the reaction between the artepillin C analogue and the DPPH radical suggest that the DPPH radical-scavenging reaction of the artepillin C analogues in deaerated MeCN proceeds via a one-step hydrogen-atom transfer from the phenolic OH group to the DPPH radical rather than an electron transfer followed by proton transfer. | |||||
| 書誌情報 |
Bulletin of the Chemical Society of Japan 巻 85, 号 8, p. 877-883, 発行日 2012-08 |
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| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 0009-2673 | |||||
| DOI | ||||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1246/bcsj.20120005 | |||||
