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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Oxidant activity of tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl radical with catechol and pyrogallol. Mechanistic
Anna Carreras1, Isaac Esparbé, Enric Brillas
1Departament de Quimica Biologica i Modelitzacio Molecular, Institut de Quimica Avancada de Catalunya (CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain.
Abstract:
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(o) = 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.
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