Nitroxide Radicals of some N -Phenyl Substituted 1,4- and 1,2-Phenylenediamines

Abstract

Several N-phenyl substituted 1,4- and 1,2-phenylenediamines were oxidized using \(\) radicals and 3-chloroperbenzoic acid. EPR spectroscopy confirmed the generation of nitroxide radicals originating from the oxidation of the bridging -NH-group. No radical products suggesting the simultaneous reaction with the NH2-group were observed. Only in the case of 1,4-phenylenediamine, a low concentration of nitroxide radical H–NO\(\)–C6H4–NH2 was obtained. In o-aminodiphenylnitroxide the steric effect of the NH2-group causes a partially asymmetrical spin density distribution in both phenyl rings.