The tautomeric persistence of electronically and sterically biased 2-quinolinones
One dozen of tailormade model 3-fluoro-2(1H)-quinolinones were synthesized, in order to be investigated by UV-, IR- and NMR spectroscopic techniques. All of these compounds were found to exist predominantly, if not exclusively, in the lactam (carboxamide, 1,2-dihydro-2-oxoquinoline) form. No tautomeric lactim (iminol, azaphenol) structure was detected. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
Keywords: acidity constants ; amide-hydroxyimine tautomerism ; 3-fluoro-2(1H)-quinolinones ; keto-enol tautomerism ; Knorr-Effenberger cyclizations ; Nuclear-Magnetic-Resonance ; Keto-Enol-Tautomerism ; Heteroaromatic Hydroxy-Compounds ; Multiwavelength Spectrophotometric Determination ; Acid Dissociation-Constants ; Gas-Phase ; Prototropic Tautomerism ; Heterocyclic-Compounds ; Equilibrium-Constants ; Ionization Constants
Record created on 2010-11-30, modified on 2016-08-09