Oxidant activity of tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl radical with catechol and pyrogallol. Mechanistic considerations.
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.
Carreras
Anna
A
Departament de Quimica Biologica i Modelitzacio Molecular, Institut de Quimica Avancada de Catalunya (CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain.
Esparbé
Isaac
I
Brillas
Enric
E
Rius
Jordi
J
Torres
Josep Lluís
JL
Julià
Luis
L
D002396:Catechols / Q000737:chemistry*; D004579:Electron Transport; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D055601:Organic Chemistry Phenomena; D016877:Oxidants / Q000737:chemistry*; D011748:Pyrogallol / Q000737:chemistry*; D012997:Solvents
D002396:Catechols; D016877:Oxidants; D012997:Solvents; D011748:Pyrogallol; C051224:methyl radical; D008697:Methane