Explanation of Substituent Effects on the Enolization of β-Diketones and β-Ketoesters

• Isolde Sandler ^[1] ; Jason B. Harper ^[1] ; Junming Ho ^[1]
  1. [1] University of New South Wales, Australia
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 98, Nº 3, 2021, págs. 1043-1048
• Idioma: inglés
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• Resumen

  • This article highlights some of the challenges in explaining simple substituent effects on keto–enol equilibria, particularly to an undergraduate audience. Quantum-chemical calculations were performed to identify the role of intramolecular hydrogen bonding, inductive effects due to electron-withdrawing groups, and cross-conjugation on the enolization of β-diketones and β-ketoesters. These insights could be applied by an instructor in order to enrich undergraduate chemistry students’ understanding of this fundamental reaction.