Reactivity of Octa(2,6-fluorophenyl)porphyrazine in Acid–Base Reactions with Nitrogenous Organic Bases

Reactions between octa(2,6-fluorophenyl)porphyrazine and pyridine, 2-methylpyridine, morpholine, piperidine, butylamine, tert-butylamine, diethylamine, and triethylamine in a benzene medium have been studied. The acid–base reactions between the macroheterocycle and piperidine or butylamine are slow processes leading to the formation of kinetically stable proton-transfer complexes. The structures of these complexes have been optimized using CAM-B3LYP/cc-pVTZ. The changes in the reactivity of octa(2,6-fluorophenyl)porphyrazine are analyzed as a function of the steric structure and proton-acceptor power of the nitrogenous base.