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Structural, spectral, and theoretical investigations of 5-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid
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  • 作者:Shivapura Viveka ; Gowda Vasantha ; Dinesha…
  • 关键词:Pyrazole ; Crystallization ; FT ; IR spectrum ; Thermo gram ; Crystal structure ; NMR ; DFT
  • 刊名:Research on Chemical Intermediates
  • 出版年:2016
  • 出版时间:May 2016
  • 年:2016
  • 卷:42
  • 期:5
  • 页码:4497-4511
  • 全文大小:1,512 KB
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  • 作者单位:Shivapura Viveka (1)
    Gowda Vasantha (2)
    Dinesha (1)
    Shivalingegowda Naveen (3)
    Neratur Krishnappagowda Lokanath (4)
    Gundibasappa Karikannar Nagaraja (1)

    1. Department of Studies in Chemistry, Mangalagangotri, Mangalore University, Konaje, 574199, India
    2. Chemistry of Interfaces, Division of Chemical Engineering, Luleå University of Technology, 97187, Luleå, Sweden
    3. Institution of Excellence, Vijnana Bhavana, Manasagangotri, University of Mysore, Mysore, 570006, India
    4. Department of Studies in Physics, Manasagangotri, University of Mysore, Mysore, 570006, India
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Catalysis
    Physical Chemistry
    Inorganic Chemistry
  • 出版者:Springer Netherlands
  • ISSN:1568-5675
文摘
The present research work has focused on combined experimental and theoretical studies of one of the biologically important pyrazole-4-carboxylic acid derivatives, viz. 5-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid (C11H10N2O2). The starting material 5-methyl-1-phenyl-1H-4-pyrazolecarboxylate (1) was obtained by the cyclocondensation of ethyl acetoacetate, N,N-dimethylformamide dimethyl acetal (DMF-DMA), and phenylhydrazine, which upon basic hydrolysis yielded the corresponding acid (2). The target compound (2) was characterized by 1H and 13C NMR (solution in DMSO), Fourier transform infrared (FT-IR) spectroscopy, thermo gravimetric analysis, and by single-crystal X-ray diffraction technique. The single crystals of compound (2) were obtained at room temperature by slow evaporation of ethanol as solvent and crystallized in the space group P2 1/n of monoclinic system. The experimental FT-IR and 1H and 13C NMR chemical shifts have been compared to those calculated by means of density functional theory (DFT) at the B3LYP/TZ2P level of theory. The continuum-like screening model was used for geometry optimization of a single molecule and for subsequent calculations of NMR shielding constants in solution (DMSO). Finally, the HOMO–LUMO energy levels were also constructed to study the electronic transition within the molecule by time-dependent TD-DFT method.

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