Linking Enol-Keto Tautomerization Ratios in β‑Diketones to Their Physical Properties Using Computational Quantum
Julia Gabriel1, Jesse Na1, Brian Guillermo1
1Rowan University, 201 Mullica Hill Road, Glassboro, New Jersey 08028, United States.
Abstract:
Tautomeric equilibria play an essential role in numerous chemical and biological reactions. Despite having structures that only differ by the position of one hydrogen atom, the chemical properties of prototropic tautomers can vary considerably, and consistently predicting their tautomer ratios remains an unsolved challenge. This project aims to determine the chemical and electronic structure factors that control the equilibrium ratio between the keto and enol forms of prototropic tautomers. We utilize computational quantum chemistry software to analyze the impact of substituent effects, intermolecular interactions, and solvent interactions (implicit and explicit) on the tautomerization ratio.
Related Concept Videos
Keto–Enol Tautomerism: Mechanism
Reactivity of Enols
Types of Enols and Enolates
Regioselective Formation of Enolates
Nitrosation of Enols
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
