Substituent, Temperature and Solvent Effects on the Keto-Enol EQUILIBRIUM in β-Ketoamides: A Nuclear Magnetic Resonance Study - Open Journal of Physical Chemistry

OJPC > Vol.3 No.4, November 2013

Volume 3, Issue 4 (November 2013)

ISSN Print: 2162-1969 ISSN Online: 2162-1977

Google-based Impact Factor: 0.32 Citations

Substituent, Temperature and Solvent Effects on the Keto-Enol EQUILIBRIUM in β-Ketoamides: A Nuclear Magnetic Resonance Study ()

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DOI: 10.4236/ojpc.2013.34017 7,333 Downloads 12,698 Views Citations

Author(s)

Sergio L. Laurella, Manuel González Sierra, Jorge J. P. Furlong, Patricia E. Allegretti

Affiliation(s)

Laboratorio LADECOR, División Química Orgánica, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata (UNLP), La Plata, Argentina.

ABSTRACT

Substituent, temperature and solvent effects on tautomeric equilibria in several β-ketoamides have been investigated by means of nuclear magnetic resonance spectroscopy (NMR). Keto-enol equilibrium predominates over the amide-imidol one. The relative stability of the individual tautomers and the corresponding equilibrium shifts are explained considering electronic and steric effects and tautomer stabilization via internal hydrogen bonds. In solution, these compounds exist mainly as ketoamide and Z-enolamide tautomers, both presenting intramolecular hydrogen bonds.

KEYWORDS

β-Ketoamides; Keto-Enol Equilibrium; Nuclear Magnetic Resonance Spectroscopy

Share and Cite:

S. Laurella, M. Sierra, J. Furlong and P. Allegretti, "Substituent, Temperature and Solvent Effects on the Keto-Enol EQUILIBRIUM in β-Ketoamides: A Nuclear Magnetic Resonance Study," Open Journal of Physical Chemistry, Vol. 3 No. 4, 2013, pp. 138-149. doi: 10.4236/ojpc.2013.34017.

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