Photoreactions of Heteroaromatic Compounds. IV. Solvent and Acidity Dependence of the Photoreactions of Nicotinic Acid and Its Derivatives

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Abstract
Nicotinic acid and its derivatives show manifold photoreactivity depending on the solvent and the acidity of the solution. The cationic form of these compounds in general undergoes photo-hydroxylation in aqueous solutions, and photo-ethylation in ethanol solutions. The anionic form of nicotinic acid is resistant to UV-irradiation in strongly alkaline aqueous solution, but undergoes photo-decarboxylation in alkaline ethanol solution. Nicotinic acid yielded 2-(3-pyridyl)-5-pyridinecarboxylic acid in aqueous solutions at pH=4–6. Photo-substitution by 1-hydroxyethyl group occurs in the neutral forms of 3-cyanopyridine and ethyl nicotinate in ethanol solution. The photoreactivity of nicotinic acid is considered on the basis of CNDO/2 calculation.

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