SPECTROSCOPIC STUDIES OF KETO–ENOL EQUILIBRIA: PART 1. SOLVENT EFFECTS
- 1 December 1962
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 40 (12) , 2267-2271
- https://doi.org/10.1139/v62-351
Abstract
Solvent effects on the keto–enol equilibria of ethyl acetoacetate, acetylacetone, ethyl cyclopentanone-2-carboxylate, and methyl 4-methylcyclopentane-1-,2-dione-3,4,5-tricarboxylate have been studied by ultraviolet spectroscopy. The extent of enolization is mainly determined by the stabilization of the keto form by local association with polar or proton-donating solvent molecules, just as in the case of n → π* transitions and infrared stretching frequencies. Solvent effects on infrared spectra reveal useful information regarding the characteristic frequencies of the tautomers.Keywords
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