Article citationsMore>>

S. Laurella, M. González Sierra, J. Furlong and P. Allegretti, “Analysis of Tautomerism in β-Ketobuanamides by Nuclear Magnetic Resonance: Substituent, Temperature and Solvent Effects,” Journal of Applied Solution Chemistry and Modeling, Vol. 1, 2012, pp. 6-12.

has been cited by the following article:

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

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

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

  JOURNAL NAME: Open Journal of Physical Chemistry, Vol.3 No.4, October 25, 2013

  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.