Influence of carboxylic acid association upon the lactim–lactam tautomeric equilibrium of 2-hydroxypyridines
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 620-623
- https://doi.org/10.1039/p29800000620
Abstract
I.r. and u.v. absorption spectroscopy in CCl4 at room temperature provides evidence for lactim–acid and lactam–acid heterodimer formation in 6-chloro-2-hydroxypyridine–acetic acid mixtures. Measurements of association constants for two types of 1:1 hydrogen-bonded complexes reveal preferential association with the lactam tautomer, leading to a shift in the apparent tautomeric equilibrium constant. These results suggest that specific interactions are of great importance in understanding solvent effects on protomeric equilibria.Keywords
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