How to drive imine-enamine tautomerism of pyronic derivatives of biological interest - A theoretical and experimental study of substituent and solvent effects - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Comptes Rendus. Chimie Année : 2010

How to drive imine-enamine tautomerism of pyronic derivatives of biological interest - A theoretical and experimental study of substituent and solvent effects

Anissa Amar
Hacène Meghezzi
  • Fonction : Auteur correspondant
  • PersonId : 945351

Connectez-vous pour contacter l'auteur
Racheddine Kaoua
  • Fonction : Auteur
Bellara Kolli
  • Fonction : Auteur

Résumé

An investigation of the tautomerism of five series of aminated pyronic compounds of pharmacological interest was carried out using NMR experiments and standard quantum mechanical B3LYP/6-311+G** calculations. The obtained results indicate that among four possible tautomers, imine and enamine forms are the two predominating ones in the gas phase as well as in solution. Depending on the nature of the substituting group, the enamine or the imine form is the most stable tautomer, the calculations being in agreement with experiment. The calculated equilibrium constants in the gas phase and in solution show that the enamine form is stabilized by polar solvents, in all cases. NBO analysis explains well the predominance of a form over another one when changing a substituting group. We give indications on how to favour the imine form which is preferred for synthesis purposes.

Dates et versions

hal-00860888 , version 1 (11-09-2013)

Identifiants

Citer

Anissa Amar, Hacène Meghezzi, Abdou Boucekkine, Racheddine Kaoua, Bellara Kolli. How to drive imine-enamine tautomerism of pyronic derivatives of biological interest - A theoretical and experimental study of substituent and solvent effects. Comptes Rendus. Chimie, 2010, 13 (5), pp.553-560. ⟨10.1016/j.crci.2009.11.009⟩. ⟨hal-00860888⟩
120 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More