Abstract
The AM1 and PM3 methods with the inclusion of a limited configuration interaction (CI) approach were used to study the stabilities of the tautomers of hexafluoroacetylacetone (HFAA). It was found that the most stable tautomer is the hydrogen bonded cyclic asymmetric enol form, the energy of which is lower than that of any keto tautomer by at least 2.5 kcal mol −1 with the AM1 model and 0.9 kcal mol −1 with the PM3 model. It was shown that HFAA should be an O-H acid. The intramolecular hydrogen bond energy is 4.5 kcal mol −1 with the AM1 model and 4.8 kcal mol −1 with the PM3 model. It was shown that proton transfer from one oxygen atom to the other is controlled by the double minimum potential curve and the correspondig energy barrier height is 24.1 kcal mol −1 with the AM1 model and 27.4 kcal mol −1 with the PM3 model.
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