73087-80-6Relevant articles and documents
Photochemical nitration by tetranitromethane. Part XXXVIII. Nitration of tris(4-bromophenyl)amine, a compound corresponding to a stable radical cation
Eberson, Lennart,Hartshorn, Michael P.,Svensson, Jan Olof
, p. 279 - 288 (2007/10/03)
The photochemical reaction between tris(4-bromophenyl)amine (TBPA) and tetranitromethane in dichloromethane or acetonitrile gave almost exclusively the nitro-debromination product, 4-nitrophenylbis(4′-bromophenyl)amine (1). In the presence of trifluoroacetic acid, the 2-nitro-substitution product, 4-bromo-2-nitrophenylbis(4′-bromophenyl)amine (3) also appeared, together with further brominated TBPAs (4). Preparative and kinetic studies of the individual reactions involved, viz. the TBPA-NO2, TBPA+-NO2 and TBPA+-trinitromethanide ion reactions, indicated that the simple regiochemistry of the photochemical reaction is due to an addition-elimination mechanism, in which the initial attack of trinitromethanide ion occurs at the carbon ipso to the nitrogen function. Acta Chemica Scandinavica 1997.
Organic Electron Transfer Agents, I. Electrochemical and Spectroscopical Study of Bromo-substituted Triarylamine Redox Systems
Schmidt, Werner,Steckhan, Eberhard
, p. 577 - 585 (2007/10/02)
The redox behaviour of the bromo-substituted triarylamines 2-7 has been studied by cyclic voltammetry.The oxidation potentials of the redox pair amine/cation radical strongly depend on the degree of substitution in ortho-position showing a smaller sterical influence in addition to a strong electronic effect.The second oxidation potential, cation radical/dication, is influenced by substitution to a much smaller degree.The UV/VIS spectra of the corresponding cation radicals are shifted bathochromically with increasing ortho-substitution.A linear relationship between redox potentials of the amines and long wave-length absorbance maxima of the cation radicals is observed.Redox potentials and UV/VIS spectra allow partial analysis of the term schemes of the amines and the corresponding cation radicals.ESR spectra of the cation radicals show broad and unresolved signals.