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A study of the tautomerism of β-dicarbonyl compounds with special emphasis on curcuminoids

AuthorsCornago, Pilar; Claramunt, Rosa M.; Bouissane, L.; Alkorta, Ibon ; Elguero, José
Issue Date2008
PublisherPergamon Press
CitationTetrahedron 64: 8089- 8094 (2008)
AbstractSix β-diketones related to curcumin and curcumin itself have been studied by 13C NMR spectroscopy in chloroform in order to determine the equilibrium constant between the two keto/enol tautomers. In order to do this GIAO/B3LYP/6-31G** calculations of absolute shieldings (σ, ppm) were carried out. To establish relationships between σ and experimental chemical shifts (δ, ppm), three simple β-diketones (acetylacetone, dibenzoylmethane and benzoylacetone) have been studied. The preference for different groups to be conjugated with the C{double bond, long}O has been determined. © 2008 Elsevier Ltd. All rights reserved.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2008.06.065
Identifiersdoi: 10.1016/j.tet.2008.06.065
issn: 0040-4020
Appears in Collections:(IQM) Artículos
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