Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium

Ikuo Nakanishi; Kentaro Miyazaki; Tomokazu Shimada; Yuko Iizuka; Keiko Inami; Masatak Mochizuki; Shiro Urano; Haruhiro Okuda; Toshihiko Ozawa; Shunichi Fukuzumi; Nobuo Ikota; Kiyoshi Fukuhara

doi:10.1039/b306758k

Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium

Ikuo Nakanishi, Kentaro Miyazaki, Tomokazu Shimada, Yuko Iizuka, Keiko Inami, Masatak Mochizuki, Shiro Urano, Haruhiro Okuda, Toshihiko Ozawa, Shunichi Fukuzumi, Nobuo Ikota, Kiyoshi Fukuhara

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

Electron-transfer reduction of molecular oxygen (O₂) by the phenolate anion (1^-) of a vitamin E model, 2,2,5,7,8-pentamethylchroman-6-ol (1H), occurred to produce superoxide anion, which could be directly detected by a low-temperature EPR measurement. The rate of electron transfer from 1^- to O₂ was relatively slow, since this process is energetically unfavourable. The one-electron oxidation potential of 1^- determined by cyclic voltammetric measurements is sufficiently negative to reduce 2,2-bis(4-tert-octylphenyl)-1-picrylhydrazyl radical (DOPPH•) to the corresponding one-electron reduced anion, DOPPH^-, suggesting that 1^- can also act as an efficient radical scavenger.

Original language	English
Pages (from-to)	4085-4088
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	1
Issue number	22
DOIs	https://doi.org/10.1039/b306758k
State	Published - 21 Nov 2003

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Nakanishi, I., Miyazaki, K., Shimada, T., Iizuka, Y., Inami, K., Mochizuki, M., Urano, S., Okuda, H., Ozawa, T., Fukuzumi, S., Ikota, N., & Fukuhara, K. (2003). Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium. Organic and Biomolecular Chemistry, 1(22), 4085-4088. https://doi.org/10.1039/b306758k

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title = "Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium",

abstract = "Electron-transfer reduction of molecular oxygen (O2) by the phenolate anion (1-) of a vitamin E model, 2,2,5,7,8-pentamethylchroman-6-ol (1H), occurred to produce superoxide anion, which could be directly detected by a low-temperature EPR measurement. The rate of electron transfer from 1- to O2 was relatively slow, since this process is energetically unfavourable. The one-electron oxidation potential of 1- determined by cyclic voltammetric measurements is sufficiently negative to reduce 2,2-bis(4-tert-octylphenyl)-1-picrylhydrazyl radical (DOPPH•) to the corresponding one-electron reduced anion, DOPPH-, suggesting that 1- can also act as an efficient radical scavenger.",

author = "Ikuo Nakanishi and Kentaro Miyazaki and Tomokazu Shimada and Yuko Iizuka and Keiko Inami and Masatak Mochizuki and Shiro Urano and Haruhiro Okuda and Toshihiko Ozawa and Shunichi Fukuzumi and Nobuo Ikota and Kiyoshi Fukuhara",

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doi = "10.1039/b306758k",

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Nakanishi, I, Miyazaki, K, Shimada, T, Iizuka, Y, Inami, K, Mochizuki, M, Urano, S, Okuda, H, Ozawa, T, Fukuzumi, S, Ikota, N & Fukuhara, K 2003, 'Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium', Organic and Biomolecular Chemistry, vol. 1, no. 22, pp. 4085-4088. https://doi.org/10.1039/b306758k

Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium. / Nakanishi, Ikuo; Miyazaki, Kentaro; Shimada, Tomokazu et al.
In: Organic and Biomolecular Chemistry, Vol. 1, No. 22, 21.11.2003, p. 4085-4088.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium

AU - Nakanishi, Ikuo

AU - Miyazaki, Kentaro

AU - Shimada, Tomokazu

AU - Iizuka, Yuko

AU - Inami, Keiko

AU - Mochizuki, Masatak

AU - Urano, Shiro

AU - Okuda, Haruhiro

AU - Ozawa, Toshihiko

AU - Fukuzumi, Shunichi

AU - Ikota, Nobuo

AU - Fukuhara, Kiyoshi

PY - 2003/11/21

Y1 - 2003/11/21

N2 - Electron-transfer reduction of molecular oxygen (O2) by the phenolate anion (1-) of a vitamin E model, 2,2,5,7,8-pentamethylchroman-6-ol (1H), occurred to produce superoxide anion, which could be directly detected by a low-temperature EPR measurement. The rate of electron transfer from 1- to O2 was relatively slow, since this process is energetically unfavourable. The one-electron oxidation potential of 1- determined by cyclic voltammetric measurements is sufficiently negative to reduce 2,2-bis(4-tert-octylphenyl)-1-picrylhydrazyl radical (DOPPH•) to the corresponding one-electron reduced anion, DOPPH-, suggesting that 1- can also act as an efficient radical scavenger.

AB - Electron-transfer reduction of molecular oxygen (O2) by the phenolate anion (1-) of a vitamin E model, 2,2,5,7,8-pentamethylchroman-6-ol (1H), occurred to produce superoxide anion, which could be directly detected by a low-temperature EPR measurement. The rate of electron transfer from 1- to O2 was relatively slow, since this process is energetically unfavourable. The one-electron oxidation potential of 1- determined by cyclic voltammetric measurements is sufficiently negative to reduce 2,2-bis(4-tert-octylphenyl)-1-picrylhydrazyl radical (DOPPH•) to the corresponding one-electron reduced anion, DOPPH-, suggesting that 1- can also act as an efficient radical scavenger.

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AN - SCOPUS:0344946138

SN - 1477-0520

VL - 1

SP - 4085

EP - 4088

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 22

ER -

Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium

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