Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: An NMR and Theoretical Study

Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: An NMR and Theoretical Study

Using nuclear magnetic resonance spectroscopy (NMR), substituent, temperature and solvent effects on tautomeric equilibria have been investigated in several β-ketoamides. Keto-enol tautomerism is observed and in this series of β-ketoamides the equilibrium of amide-imidol is not detectable. In solution, these compounds exist primarily as ketoamide and Z-enolamide tautomers, both forming intramolecular hydrogen bonds. Considering the electronic and steric effects and tautomer stabilisation through internal hydrogen bonds, the relative stability of the individual tautomers and the subsequent equilibrium shifts are clarified. Theoretical calculations endorse those assumptions.

Author (s) Details

Diego D. Colasurdo
CEDECOR (Centro de Estudio de Compuestos Orgánicos), Facultad de Ciencias Exactas, Universidad Nacional de La Plata (UNLP), Calle 115 y 47, (1900) La Plata, Argentina and CONICET (Consejo Nacional de Investigaciones Científicas y Técnicas), Argentina.

Dr. Patricia E. Allegretti
CEDECOR (Centro de Estudio de Compuestos Orgánicos), Facultad de Ciencias Exactas, Universidad Nacional de La Plata (UNLP), Calle 115 y 47, (1900) La Plata, Argentina and CIC-BA (Comisión de Investigaciones Científicas de la Provincia de Buenos Aires), Argentina.

Dr. Sergio L. Laurella
CEDECOR (Centro de Estudio de Compuestos Orgánicos), Facultad de Ciencias Exactas, Universidad Nacional de La Plata (UNLP), Calle 115 y 47, (1900) La Plata, Argentina and CIC-BA (Comisión de Investigaciones Científicas de la Provincia de Buenos Aires), Argentina.

View Book :- https://bp.bookpi.org/index.php/bpi/catalog/book/282

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