Influence of intramolecular hydrogen bonds on the tautomeric equilibrium of 1,3-diketones |
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| Authors: | D Zheglova N Denkov AI Kol&#x;tsov |
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| Institution: | Department of Chemistry, University of Sofia Bulgaria;Institute of High Molecular Compounds, Academy of Sciences of the USSR, Leningrad 199164 U.S.S.R. |
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| Abstract: | 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 are keto-enol equilibrium toward the keto-tautomer and enol-enol equilibrium toward the tautomer with an enolized aliphatic carbonyl group. |
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