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the claim

Specific thermodynamic and electronic factors determine the keto-enol tautomeric ratio in carbonyl compounds

the verdict
SUPPORTED
the evidence backs this
Recorded sources
5 sources for · 0 against

Counts group repeated records of the same source within each side. They do not measure evidence strength or source independence.

Multiple studies using thermodynamic measurements and electronic calculations confirm that specific energetic and electronic factors dictate the keto-enol tautomeric ratio.

The analysis

All five papers provide direct evidence that thermodynamic parameters (enthalpies, solvent effects, ring strain) and electronic factors (substituent effects, Hammett correlations) control keto-enol tautomerism and equilibrium ratios.

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
Recorded source metadata

Max T. Rogers, Jane L. Burdett. KETO–ENOL TAUTOMERISM IN β-DICARBONYLS STUDIED BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY: II. SOLVENT EFFECTS ON PROTON CHEMICAL SHIFTS AND ON EQUILIBRIUM CONSTANTS. 1965. https://doi.org/10.1139/v65-202

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
Recorded source metadata

Jack Hine, Kazushi Arata. Keto-Enol Tautomerism. II. The Calorimetrical Determination of the Equilibrium Constants for Keto-Enol Tautomerism for Cyclohexanone and Acetone. 1976. https://doi.org/10.1246/bcsj.49.3089

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
Recorded source metadata

Jack Hine, Kazushi Arata. Keto-Enol Tautomerism. I. The Calorimetrical Determination of the Equilibrium Constant for Keto-Enol Tautomerism for Cyclopentanone. 1976. https://doi.org/10.1246/bcsj.49.3085

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
Recorded source metadata

Xudong Yao, Ralph M Pollack. Electronic effects on enol acidity and keto-enol equilibrium constants for ring-substituted 2-tetralones. 1999. https://doi.org/10.1139/v99-006

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
Recorded source metadata

Luqman Idd Juma, Rene Costa. A density functional theory study of keto-enol tautomerism in 1,2-cyclodiones: Substituent effects on reactivity and thermodynamic stability. 2024. https://doi.org/10.1177/17475198241305254

Uses density functional theory to confirm that substituents and thermodynamic stability dictate keto-enol tautomerism.

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first checked01 Aug 2026
judged → SUPPORTED · 8801 Aug 2026
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