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

被引：65

作者：

Cornago, Pilar ^{[1
]}

Claramunt, Rosa M. ^{[1
]}

Bouissane, Latifa ^{[1
]}

Alkorta, Ibon ^{[2
]}

Elguero, Jose ^{[2
]}

机构：

[1] Univ Nacl Educ Distancia, Fac Ciencias, Dept Quim Organ & Bioorgan, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

TETRAHEDRON | 2008年 / 64卷 / 35期

关键词：

NMR; beta-diketones; curcumin; GIAO; DFT;

D O I：

10.1016/j.tet.2008.06.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Six beta-diketones related to curcumin and curcumin itself have been studied by C-13 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 (sigma, ppm) were carried out. To establish relationships between sigma and experimental chemical shifts (delta, ppm), three simple beta-diketones (acetylacetone, dibenzoylmethane and benzoylacetone) have been studied. The preference for different groups to be conjugated with the C=O has been determined. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：8089 / 8094

页数：6

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