Factors affecting stability and equilibria of free radicals—IX: Non-equivalence of aryl groups in 1,1-diaryl-2-benzenesulphonyl-hydrazyls and related compounds

Abstract

1,1-Bis-(3',5'-di-t-butylphenyl)-2-benzenesulphonyl-hydrazine 11 and the corresponding 2-picryl-hydrazine 13 were synthesized. Oxidation of 11 afforded the stable hydrazyl 12 whose ESR spectrum could be simulated in terms of three hyperfine coupling constants. These experimental data leave no alternative but to assign larger proton hyperfine coupling constants to one aryl group in 12 than to the other. This non-equivalence was interpreted in terms of the Linnett theory. The picrylhydrazyl 14 does not give completely resolved ESR spectra. Structures were ascertained by IR, UV-vis, 1H NMR and 13C NMR spectra.