Synthesis, characterization, single crystal X-ray diffraction and DFT studies of ethyl 5-methyl-1-phenyl-1H-pyrazole-4-carboxylate

The present study describes the synthesis, spectroscopic, and single crystal X-ray structural analysis of ethyl 5-methyl-1-phenyl-1H-pyrazole-4-carboxylate. The pyrazole ester of formula [C 13 H 14 N 2 O 2 ] was prepared from the three-component one-pot condensation reaction of ethyl acetoacetate, N...

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Bibliographic Details
Published in:Molecular Crystals and Liquid Crystals 2016-04, Vol.629 (1), p.135-145
Main Authors: Viveka, S., Vasantha, G., Dinesha, Naveen, S., Lokanath, N. K., Nagaraja, G. K.
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry of Interfaces
crystal structure
Crystallization
DFT
Diffraction
Electronics
FTIR spectrum
Gränsytors kemi
Molecular structure
Phenyls
pyrazole
Single crystals
Synthesis
thermogram
Thermography
Unit cell
X-rays
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Summary:The present study describes the synthesis, spectroscopic, and single crystal X-ray structural analysis of ethyl 5-methyl-1-phenyl-1H-pyrazole-4-carboxylate. The pyrazole ester of formula [C 13 H 14 N 2 O 2 ] was prepared from the three-component one-pot condensation reaction of ethyl acetoacetate, N,N-dimethyldimethoxymethanamine, and phenyl hydrazine. The product was crystallized by using ethanol as solvent. The structure of the compound was confirmed by elemental analysis, Fourier transforms infrared (IR), thermogravimetric analysis, UV-visible (UV-Vis), 1 H NMR, and single-crystal X-ray diffraction studies. The gas-phase molecular geometry and the electronic structure-property of the molecule were calculated at the density functional theory. The frontier molecular orbitals, theoretical UV-Vis, and IR stretching vibrations were also reported. The compound crystallizes in the monoclinic system with the space group P2 1 /c and Z = 4. The unit cell parameters are a = 12.141(3) Å, b = 13.934(4) Å, c = 7.2777(18) Å, and β = 97.816(14) 0 . The structure is stabilized by an intermolecular interaction of type C-H···O and the structure also involves C-H···π interactions.
ISSN:1542-1406
1563-5287
1563-5287
1527-1943
DOI:10.1080/15421406.2015.1107813