Kinetics of proton transfer from tetra(m-trifluoromethylphenyl)dibenzotetraazaporphin to nitrogen-containing bases in a benzene-dimethyl sulfoxide system

Abstract

The acid-base interaction between tetra(m-trifluoromethylphenyl)dibenzotetraazaporphin with pyridine, 2-methylpyridine, morpholine, piperidine, n-butylamine, diethylamine, and triethylamine is studied in the benzene-dimethyl sulfoxide system. It is found that intermolecular transfer of protons of NH-groups from of tetra(m-trifluoromethylphenyl)dibenzotetraazaporphin to n-butylamine and piperidine is characterized by unusually low values of the rate constants. The effect the structure of tetra(m-trifluoromethylphenyl)dibenzotetraazaporphin, hexa(m-trifluoromethylphenyl)benzotetraazaporphin, and octa(m-trifluoromethylphenyl)tetraazaporphin has on the kinetic parameters of acid-base interaction is demonstrated, along with that of the nature of the base and solvent. A structure is proposed for the charge-transfer complexes of the substituted tetraazaporphyrins. It is found that they undergo destruction over time.