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

  • Laurella S
  • Sierra M
  • Furlong J
  • et al.
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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 consider-ing 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.

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Laurella, S. L., Sierra, M. G., Furlong, J. J. P., & Allegretti, P. E. (2013). Substituent, Temperature and Solvent Effects on the Keto-Enol EQUILIBRIUM in β -Ketoamides: A Nuclear Magnetic Resonance Study. Open Journal of Physical Chemistry, 03(04), 138–149. https://doi.org/10.4236/ojpc.2013.34017

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