Journal of Molecular Structure p. 371 - 374 (1984)
Update date:2022-08-11
Topics:
Zheglova, D.
Denkov, N.
Kol'tsov, A. I.
The paper deals with a quantitative characterization of the influence of multiple intramolecular hydrogen bonds on the tautomeric equilibrium of 1,3-diketones by means of NMR-spectroscopy.The contents of the keto- and two enol forms of 1-(o-hydroxyphenyl)-1,3-butandione and 1-(o-methoxyphenyl)-1,3-butandione in tetrachloromethane, deuterochloroforme, acetone-d6 and acetonitrile-d3 are compared.The intramolecular hydrogen bond between the phenolic hydroxyl group and the aromatic carbonyl group in 1-(o-hydroxyphenyl)-1,3-butandione shifts the keto-enol equilibrium toward the keto-tautomer and enol-enol equilibrium toward the tautomer with an enolized aliphatic carbonyl group.
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