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Crystals 2015, 5(1), 100-115; doi:10.3390/cryst5010100

Synthesis, Crystal and Molecular Structure Studies and DFT Calculations of Phenyl Quinoline-2-Carboxylate and 2-Methoxyphenyl Quinoline-2-Carboxylate; Two New Quinoline-2 Carboxylic Derivatives

1
Department of Chemistry, Yuvarajaʼs College, University of Mysore, Mysore-570 005, India
2
Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
3
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
4
Spice and Flavor Science Department, CSIR-Central Food Technological Research institute, Mysore 570005, India
*
Author to whom correspondence should be addressed.
Academic Editor: Ivana R. Evans
Received: 15 December 2014 / Revised: 8 January 2015 / Accepted: 12 January 2015 / Published: 12 February 2015
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Abstract

The crystal and molecular structures of the title compounds, phenyl quinoline-2-carboxylate and 2-methoxyphenyl quinoline-2-carboxylate, two new derivatives of quinolone-2-carboxylic acid, are reported and confirmed by single crystal X-ray diffraction and spectroscopic data. Compound (I), C16H11NO2, crystallizes in the monoclinic space group P21/c, with 8 molecules in the unit cell. The unit cell parameters are a = 14.7910(3) Å; b = 5.76446(12) Å; c = 28.4012(6) Å; β = 99.043(2)°; V = 2391.45(9) Å3. Compound (II), C17H13NO5, crystallizes in the monoclinic space group P21/n with 4 molecules in the unit cell. The unit cell parameters are a = 9.6095(3) Å; b = 10.8040(3) Å; c = 13.2427(4) Å; β = 102.012(3)°; V = 1344.76(7) Å3. Density functional theory (DFT) geometry optimized molecular orbital calculations were performed and frontier molecular orbitals of each compound are displayed. Correlation between the calculated molecular orbital energies (eV) for the surfaces of the frontier molecular orbitals to the electronic excitation transitions from the absorption spectra of each compound has been proposed. Additionally, similar correlations observed among six closely related compounds examining small structural differences to their frontier molecular orbital surfaces and from their DFT molecular orbital energies, provide further support for the suggested assignments of the title compounds. View Full-Text
Keywords: X-ray crystal structure; DFT molecular orbital calculations; frontier molecular orbitals X-ray crystal structure; DFT molecular orbital calculations; frontier molecular orbitals
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MDPI and ACS Style

Fazal, E.; Jasinski, J.P.; Anderson, B.J.; Kaur, M.; Nagarajan, S.; Sudha, B.S. Synthesis, Crystal and Molecular Structure Studies and DFT Calculations of Phenyl Quinoline-2-Carboxylate and 2-Methoxyphenyl Quinoline-2-Carboxylate; Two New Quinoline-2 Carboxylic Derivatives. Crystals 2015, 5, 100-115.

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