Electrochemical and ESR Spectroscopic Study of 2,7-Disubstituted Phenazines

概要

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Cyclic voltammetry (CV) for 2,7-disubstituted phenazines (1mM, MeO (1), EtO (2), H (3), Cl (4), Br (5), COOEt (6)) was carried out in acetonitrile containing trifluoroacetic acid (TFA, 1% and 2%) and NaClO_4 (0.1M) as a supporting electrolyte under N_2 gas. Phenazines showed two cathodic peaks (E_<pc1> and E_<pc2>) and these peaks had counterparts (E_<pa1> and E_<pa2>, respectively). Plots of the peak potentials against σ_p were linear. The first cathodic wave corresponds to the reduction of singly protonated phenazines followed by proton transfer. The second cathodic wave corresponds to the reduction of the cation radical of dihydrophenazines to produce dihydrophenazine as a final product.ESR spectrometry of 1-6 in acetonitrile and in acetonitrile containing 1% TFA was conducted and computer simulation of the spectra was carried out. Splitting due to halogen or o-alkyl substituents was observed. Molecular orbital (MO) calculation of anion radicals generated from 1-6 and cation radicals generated from doubly protonated 1-6 did not give good agreement with the results of ESR spectrometry.
公益社団法人日本薬学会の論文
1996-08-15