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Molecules 2013, 18(1), 877-893; doi:10.3390/molecules18010877
Article

Synthesis, Crystal Structure, Vibration Spectral, and DFT Studies of 4-Aminoantipyrine and Its Derivatives

1,2, 3, 4, 2,* , 1,*  and 4,*
Received: 26 November 2012; in revised form: 2 January 2013 / Accepted: 5 January 2013 / Published: 11 January 2013
(This article belongs to the Section Organic Synthesis)
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Abstract: Three compounds derived from 4-aminoantipyrine (AA) were synthesized and their structures confirmed by melting point, elemental analysis, FT-IR, and 1H-NMR. The molecular structures of the four compounds were characterized by single-crystal X-ray diffraction and calculated by using the density functional theory (DFT) method with 6-31G (d) basis set. The calculated molecular geometries and the vibration frequencies of the AA derivatives in the ground state have been compared with the experimental data. The results show that the optimized geometries can reproduce well the crystal structural parameters, and the theoretical vibration frequencies show good agreement with the experimental data, although the experimental data are different from the theoretical ones due to the intermolecular forces. Besides, the molecular electrostatic potential (MEP) and the frontier molecular orbital (FMO) analysis of the compounds were investigated by theoretical calculations.
Keywords: 4-aminoantipyrine derivatives; X-ray structure determination; IR spectroscopy; DFT calculations; electronic structure properties 4-aminoantipyrine derivatives; X-ray structure determination; IR spectroscopy; DFT calculations; electronic structure properties
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Li, Y.; Liu, Y.; Wang, H.; Xiong, X.; Wei, P.; Li, F. Synthesis, Crystal Structure, Vibration Spectral, and DFT Studies of 4-Aminoantipyrine and Its Derivatives. Molecules 2013, 18, 877-893.

AMA Style

Li Y, Liu Y, Wang H, Xiong X, Wei P, Li F. Synthesis, Crystal Structure, Vibration Spectral, and DFT Studies of 4-Aminoantipyrine and Its Derivatives. Molecules. 2013; 18(1):877-893.

Chicago/Turabian Style

Li, Yi; Liu, Yuanyuan; Wang, Haowei; Xiong, Xiaohui; Wei, Ping; Li, Fangshi. 2013. "Synthesis, Crystal Structure, Vibration Spectral, and DFT Studies of 4-Aminoantipyrine and Its Derivatives." Molecules 18, no. 1: 877-893.


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