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

摘要

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