Displacement of protomeric equilibriums by self-association: hydroxypyridine-pyridone and mercaptopyridine-thiopyridone isomer pairs

P Beak, JB Covington, SG Smith…

Index: Beak, Peter; Covington, Johnny B.; Smith, Stanley G.; White, J. Matthew; Zeigler, John M. Journal of Organic Chemistry, 1980 , vol. 45, # 8 p. 1354 - 1362

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Citation Number: 111

Abstract

These results provide quantitative evidence for significant differences in the positions of protomeric equilibria for self-associated and monomeric species. The 2-substituted isomers are associated as well-known dimers while the 4-substituted systems form oligomers. In polar and hydrogen-bonding solvents self-association is substantially reduced. Sterically hindered 2- and 4-pyridones are less associated than unhindered systems. The implication of these ...