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

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• 作者：Carla I. Nieto ; Pilar Cabildo ; Rosa M. Claramunt ; Pilar Cornago…
• 关键词：Tautomerism ; β ; Diketones ; 13C and 19F NMR ; Solid ; state NMR ; GIAO calculations ; Quantum ESPRESSO calculations
• 刊名：Structural Chemistry
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：27
• 期：2
• 页码：705-730
• 全文大小：2,045 KB
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• 作者单位：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. Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Paseo Senda del Rey, 9, 28040, Madrid, Spain
  2. Departamento de Química Inorgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid (UCM), 28040, Madrid, Spain
  3. CAI de Difracciόn de Rayos-X, Facultad de Ciencias Químicas, Universidad Complutense de Madrid (UCM), 28040, Madrid, Spain
  4. Departamento de Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, and IFIBA, CONICET, Ciudad Universitaria. Pab. I, 1428, Buenos Aires, Argentina
  5. Instituto de Química Médica, Centro de Química Orgánica “Manuel Lora-Tamayo”, CSIC, Juan de la Cierva, 3, 28006, Madrid, Spain
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Computer Applications in Chemistry
  Physical Chemistry
  Theoretical and Computational Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-9001

文摘

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.