Add time:07/26/2019 Source:sciencedirect.com
Keto–enol tautomerism is a key phenomenon which determines the pharmacological activity of compounds possessing the carbonyl group. In the present study we use X-ray analysis, IR spectroscopy as well as quantum chemical calculation to address the keto–enol tautomerism of 4-substituted 3-[1-methylpyrrol-2-yl)methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with antimicrobial activity. In the gas phase and in the crystalline state all the investigated molecules exist in the keto form while in the chloroform solution a small amount of the enol form in the equilibrium with the keto form is observed. The results of the calculations are in good agreement with experimental data obtained from X-ray analysis and IR spectroscopy in KBr but do not confirm the shift of the tautomeric equilibrium into the enol form in a chloroform solution.
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