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Hyperconjugative π → σ*(CF) Interactions Stabilize the Enol Form of Perfluorinated Cyclic Keto–Enol Systems

Lindner and Lemal showed that perfluorination of keto–enol systems significantly shifts the equilibrium toward the enol tautomer. Quantum mechanical calculations now reveal that the shift in equilibrium is the result of the stabilization of the enol tautomer by hyperconjugative π → σ*(CF) interactio...

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Publicado en:J Org Chem
Main Authors: Levandowski, Brian J., Raines, Ronald T., Houk, K. N.
Formato: Artigo
Idioma:Inglês
Publicado: 2019
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Acceso en liña:https://ncbi.nlm.nih.gov/pmc/articles/PMC6995339/
https://ncbi.nlm.nih.gov/pubmed/30990687
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1021/acs.joc.9b00825
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