Linking Enol–Keto Tautomerization Ratios in β-Diketones to Their Physical Properties Using Computational Quantum Chemistry

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.