Specific thermodynamic and electronic factors determine the keto-enol tautomeric ratio in carbonyl compounds
the verdict
SUPPORTED
the evidence backs this
confidence 88/100
Multiple studies using thermodynamic measurements and electronic calculations confirm that specific energetic and electronic factors dictate the keto-enol tautomeric ratio.
Evidence for · 5
KETO–ENOL TAUTOMERISM IN β-DICARBONYLS STUDIED BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY: II. SOLVENT EFFECTS ON PROTON CHEMICAL SHIFTS AND ON EQUILIBRIUM CONSTANTS
1965 · cited by 112
Demonstrates that solvent effects and hydrogen bonding alter the keto-enol equilibrium constant.
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More for · 4
Keto-Enol Tautomerism. II. The Calorimetrical Determination of the Equilibrium Constants for Keto-Enol Tautomerism for Cyclohexanone and Acetone
1976 · cited by 36
Utilizes calorimetric measurements of enthalpies to determine thermodynamic equilibrium constants for keto-enol tautomerism.
Keto-Enol Tautomerism. I. The Calorimetrical Determination of the Equilibrium Constant for Keto-Enol Tautomerism for Cyclopentanone
1976 · cited by 12
Calculates specific thermodynamic values like enthalpy for the ketonization and enol content of cyclopentanone.
Electronic effects on enol acidity and keto-enol equilibrium constants for ring-substituted 2-tetralones
1999 · cited by 4
Shows through Hammett plots that electronic substituent effects directly influence keto-enol equilibrium constants.
A density functional theory study of keto-enol tautomerism in 1,2-cyclodiones: Substituent effects on reactivity and thermodynamic stability
2024 · cited by 2
Uses density functional theory to confirm that substituents and thermodynamic stability dictate keto-enol tautomerism.