Kinetics of proton transfer from hexa(m-trifluoromethylphenyl)benzotetraazaporphine to nitrogen-containing bases in benzene

Abstract

Acid-base interactions of hexa(m-trifluoromethylphenyl)benzotetraazaporphine with pyridine, 2-methylpyridine, morpholine, benzylamine, piperidine, n-butylamine, diethylamine, triethylamine, and tert-butylamine in benzene are studied. It is found that intermolecular proton transfer from the NH groups of hexa(m-trifluoromethylphenyl)benzotetraazaporphine to n-butylamine and piperidine is characterized by unusually low values of rate constants. The effect of the structure of hexa(m-trifluoromethylphenyl)benzotetraazaporphine and octa(m-trifluoromethylphenyl)tetraazaporphine, and the nature of the base on the kinetic parameters of acid-base interactions, is demonstrated. A structure for proton-transfer complexes of substituted tetraazaporphines is proposed. It is found that they decompose over time.