Structural Chemistry

, Volume 27, Issue 2, pp 705–730 | Cite as

The structure of β-diketones related to curcumin determined by X-ray crystallography, NMR (solution and solid state) and theoretical calculations

  • Carla I. Nieto
  • Pilar Cabildo
  • Rosa M. Claramunt
  • Pilar Cornago
  • Dionisia Sanz
  • M. Carmen Torralba
  • M. Rosario Torres
  • Marta B. Ferraro
  • Ibon Alkorta
  • Marta Marín-Luna
  • José Elguero
Original Research

Abstract

Structural data are reported on sixteen ketoenols of β-diketones: solution NMR, solid-state NMR (CPMAS and MAS) and X-ray crystallography (four compounds, where three are new). The emphasis is on the tautomerism between both ketoenols, in solution and in the solid state. GIAO/B3LYP/6-311++G(d,p) and Quantum ESPRESSO (QE) calculations were used and compared. For average values, the GIAO/DMSO-PCM is enough, but splittings can only be approached by using QE. A case of rotational disorder has been analyzed. Some anomalies related to C–F bonds and to the C–CF3 group have been detected.

Keywords

Tautomerism β-Diketones 13C and 19F NMR Solid-state NMR GIAO calculations Quantum ESPRESSO calculations 

Supplementary material

11224_2015_704_MOESM1_ESM.doc (981 kb)
Supplementary material 1 (DOC 981 kb)

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Carla I. Nieto
    • 1
  • Pilar Cabildo
    • 1
  • Rosa M. Claramunt
    • 1
  • Pilar Cornago
    • 1
  • Dionisia Sanz
    • 1
  • M. Carmen Torralba
    • 2
  • M. Rosario Torres
    • 3
  • Marta B. Ferraro
    • 4
  • Ibon Alkorta
    • 5
  • Marta Marín-Luna
    • 5
  • José Elguero
    • 5
  1. 1.Departamento de Química Orgánica y Bio-Orgánica, Facultad de CienciasUNEDMadridSpain
  2. 2.Departamento de Química Inorgánica I, Facultad de Ciencias QuímicasUniversidad Complutense de Madrid (UCM)MadridSpain
  3. 3.CAI de Difracciόn de Rayos-X, Facultad de Ciencias QuímicasUniversidad Complutense de Madrid (UCM)MadridSpain
  4. 4.Departamento de Física, Facultad de Ciencias Exactas y NaturalesUniversidad de Buenos Aires, and IFIBA, CONICETBuenos AiresArgentina
  5. 5.Instituto de Química Médica, Centro de Química Orgánica “Manuel Lora-Tamayo”CSICMadridSpain

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