Effect of the heteroatom on the one-electron reduction of ?-nitro derivatives of five-membered heterorings

Abstract

The potentials of the first polarographic half waves of the electrical reduction in dimethylformamide (DMF) of α-nitro derivatives of furan, thiophene, selenophene, and their analogs in the benzene series and the hfs constants of the EPR spectra of the electrochemically generated anion radicals of these compounds are presented. It was established that these parameters in the series of examined heterorings regularly follow the electron affinities of the heteroatoms in their s2p2pp valence state. The relative conductivity of the electronic effects of substituents is higher (1.08) in the level of the unpaired electron of the furan ring, while the conductivities in the thiophene (0.95) and selenophene (0.94) ring are lower, than in the case of the benzene ring. The conductivity through the heterorings in the molecular state is higher by a factor of 1.2 than in the level of the unpaired electron.