Oxidant Activity of Tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl Radical with Catechol and Pyrogallol. Mechanistic Considerations

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• 作者：Anna Carreras^&#8224 ; ; Isaac Esparb^‡ ; ; Enric Brillas^‡ ; ; Jordi Rius^§ ; ; Josep Llus Torres^&#8224 ; ; Luis Juli*^&#8224 ;
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：March 20, 2009
• 年：2009
• 卷：74
• 期：6
• 页码：2368-2373
• 全文大小：215K
• 年卷期：v.74,no.6(March 20, 2009)
• ISSN：1520-6904

文摘

The reducing activity of simple polyphenols (PhOH), catechol and pyrogallol, is tested in different solvents in front of tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl (HNTTM) radical, a stable organic free radical of the TTM series. HNTTM radical is very active in electron-transfer reactions to give a very stable anion. The standard potential for the reduction of HNTTM radical by cyclic voltammetry in different solvents is E° = 0.60 ± 5 V vs SCE. In hydroxylic solvents, the electron transfer is a very rapid process and the electron-donating species is the ionized PhO⁻, whereas in nonpolar solvents, it is suggested that the electron transfer is facilitated by the formation of an intermediate complex between HNTTM and PhOH.