A new method to study antioxidant capability:: Hydrogen transfer from phenols to a prefluorescent nitroxide

被引：55

作者：

Aliaga, C ^{[1
]}

Aspée, A ^{[1
]}

Scaiano, JC ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 22期

关键词：

D O I：

10.1021/ol035589w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[ABSTRACT] Rate constants for hydrogen abstraction from phenols by a prefluorescent-TEMPO probe are reported. The nitroxide is employed as a potential model of peroxyl radicals. The probe works by nitroxide suppression of the fluorescence of the chromophore. The fluorescence is restored when the nitroxide abstracts a hydrogen atom to produce the diamagnetic hydroxylamine. The phenols studied in this project exhibited rate constants between 0.003 and 0.2 M-1 s(-1). A deuterium isotope effect of 10 for TROLOX confirms that the mechanism is dominated by hydrogen transfer.

引用

页码：4145 / 4148

页数：4

共 32 条

[1] Neutron diffraction study of a phenol-nitroxide radical adduct: A structural model for hydrogen atom abstraction by peroxyl radicals from vitamin E and related phenolic antioxidants [J].