Structures of 2-hydroxypyridine and its vinyl derivatives

The PMR, Raman, and UV absorption spectra of 2-hydroxypyridine and its vinyl derivatives were investigated. Their electrochemical reduction was studied, and a quantum-chemical analysis of them was performed. It was concluded that the structure of 2-hydroxypyridine in proton-donor solvents is mesomeric, and its wave function, to a first approximation, is a linear combination of the wave functions of the 2-pyridone and zwitterion models. The contribution of the wave functions of each of the models depends substantially on the concentration of the solution and the nature of the solvent. An assumption was made regarding the presence of dynamic conjugation between the vinyl group and the ring in vinyl derivatives of 2-hydroxypyridine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 95–102 January, 1972.