Journal of Organic Chemistry p. 1626 - 1628 (1980)
Update date:2022-08-11
Topics:
Grande, Karen D.
Rosenfeld, Stuart M.
Tautomeric equilibria in acetoacetic acid have been examined by 1H NMR and found to be strongly solvent dependent.Values for enol tautomer range from less than 2percent in deuterium oxide to 49percent in carbon tetrachloride.Chemical shift data suggest that the enol tautomer is internally hydrogen bonded in the less polar solvents and that internal hydrogen bonding is unimportant for the keto tautomer.The acid probably exists in the keto form in the solid state.
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