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Change of the tautomeric preference for radical cation of pyruvic acid. DFT studies in the gas phase.

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Keto-enol tautomerism was investigated for ionized pyruvic acid using the DFT(B3LYP) method and the larger basis sets [6-31++G(d,p), 6-311++G(3df, 3pd) and aug-cc-pVDZ]. Change of the tautomeric preference was observed when going from the neutral to ionized tautomeric mixture. Ionization favors the enolization process (keto(right arrow)enol) of pyruvic acid, whereas the ketonization (keto(left arrow)enol) is preferred for the neutral system. Ionization influences also (pi)-electron delocalization, which increases exceptionally in the enol form, and slightly decreases in the keto form.

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