Abstract
The relative stabilities of tautomers of 3-acetyl- ( 1), 3-formyl- ( 2) and 3-nitrotetronic ( 3) acids are calculated by using the MNDO approach. Estimated thermodynamic parameters indicate that for 1 and 2 the ex—enol tautomeric pair b ⇌ d is ca. 5 kcal mol −1 more stable than the corresponding endo—enol tautomers. In contrast, end—enol tautomers (a ⇌ c) of 3 appear to be more stable by ca. 3 kcal mol −1 relative to their exo — enol counterparts. Differences in total energies of tautomers are elucidated by the energy partitioning technique. The role of solvation is briefly discussed at a qualitative level. If the solvation effects are taken into account the ratios of tautomers is in qualitative accordance with NMR measurements.
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