Carbonyl-enol tautomerization can occur intramolecularly
Carbonyl-enol tautomerization frequently proceeds via intramolecular proton transfer mechanisms, such as through intramolecular hydrogen bonding and excited-state intramolecular proton transfer (ESIPT).
The retrieved papers consistently provide theoretical and experimental evidence showing that keto-enol and related tautomerization processes can and do occur intramolecularly via proton transfer mechanisms, often facilitated by internal hydrogen bonding or conformational geometries.
Bülent Balta, Viktorya Aviyente. Solvent effects on glycine. I. A supermolecule modeling of tautomerization via intramolecular proton transfer. 2003. https://doi.org/10.1002/jcc.10341
Investigates glycine tautomerization via intramolecular proton transfer.
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Bülent Balta, Viktorya Aviyente. Solvent effects on glycine II. Water‐assisted tautomerization. 2004. https://doi.org/10.1002/jcc.10422
Compares intramolecular proton transfer channels with water-assisted tautomerization pathways in glycine.
Adijiang A, Ge Y, Feng H, Yan Y, Zuo X, Wang H, Zhao X, Tan M, Zhang S, Xu X, Chen L, Wang C, Li Z, Xiang D. Regulating enol-keto tautomerism at the single-molecule level with a confined optical field.. 2025. https://doi.org/10.1039/d5sc06085k
Discusses beta-diketones existing dominantly in the enol form stabilized by intramolecular hydrogen bonds.
Asatryan R, Hudzik J, Amiri V, Swihart MT. Internally Catalyzed Hydrogen Atom Transfer (<i>I-CHAT</i>)-A New Class of Reactions in Combustion Chemistry.. 2025. https://doi.org/10.3390/molecules30030524
Identifies an intramolecular catalytic hydrogen transfer mechanism leading to enol-hydroperoxide tautomers.
Estévez L, Otero N. Insights into tautomerism and pH effects on the photoluminescence of citric acid-derived molecular fluorophores.. 2026. https://doi.org/10.1039/d6ra00206d
Examines excited-state intramolecular proton transfer (ESIPT) processes in molecular fluorophores.
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