Simultaneous participation of several excited states in photochemical methoxylation and methylation of 3-pyridinecarboxamide in methanol

The UV-irradiation of 3-pyridinecarboxamide in methanol in the presence of sulfuric acid brings about methoxylation (ionic reaction) at the 2- and 6-position and methylation (radical reaction) at the 4- and 6-position. The effects of quenchers indicate that two methylation products originate from one excited triplet state which is quenched by energy transfer mechanism and that two methoxylation products originate from two different excited singlet states which are quenched by electron transfer mechanism.