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

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 cor...

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Bibliographic Details
Authors: Laurella, Sergio Luis, González Sierra, Manuel, Furlong, Jorge Javier Pedro, Allegretti, Patricia Ercilia
Format: article
Status:Published version
Publication Date:2013
Country:Argentina
Institution:Universidad Nacional de La Plata
Repository:SEDICI (UNLP)
Language:English
OAI Identifier:oai:sedici.unlp.edu.ar:10915/81150
Online Access:http://sedici.unlp.edu.ar/handle/10915/81150
Access Level:Open access
Keyword:Química
β-Ketoamides
Keto-Enol Equilibrium
Description
Summary: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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