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Crystals 2017, 7(9), 259;

Synthesis, Characterization and DFT Calculations of 4,5,12- and 1,8,12-trichloro-9,10-dihydro-9,10-ethanoanthracene-12-carbonitriles

Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Department of Chemistry, Rabigh College of Science and Art, P.O. Box 344, Rabigh 21911, Saudi Arabia
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, 21321 Alexandria, Egypt
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt
Authors to whom correspondence should be addressed.
Academic Editor: Jacob Overgaard
Received: 6 July 2017 / Revised: 14 August 2017 / Accepted: 15 August 2017 / Published: 25 August 2017
(This article belongs to the Special Issue Experimental and Theoretical Electron Density Analysis of Crystals)
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The chlorinated ethanoanthracenes: 4,5,12- and 1,8,12-(trichloro-9,10-dihydro-9,10-ethanoanthracene-12-carbonitriles) (1 and 2), which are regioisomers, were synthesized and characterized using nuclear magnetic resonance (1H- and 13C-NMR) and infrared (IR) spectroscopic techniques. The structure of isomer 1 was further confirmed using a single-crystal X-ray technique. The relative stabilities of the title compounds were calculated using the density functional theory (DFT) method on the basis of their total energies and thermodynamic parameters. Isomer 1 is thermodynamically more stable than isomer 2 in the gas phase and in solution. The calculated molecular geometry of isomer 1 agreed well with the experimental X-ray structure. The atomic charge distribution at the different atomic sites was calculated using natural bond orbital analysis. Isomer 2 was predicted to be more polar than isomer 1. View Full-Text
Keywords: synthesis; ethanoanthracene; Diels-Alder cycloaddition; X-ray; DFT synthesis; ethanoanthracene; Diels-Alder cycloaddition; X-ray; DFT

Figure 1

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Sultan, M.A.; Karama, U.; Almansour, A.I.; Soliman, S.M.; Ghabbour, H.A.; Mabkhot, Y.N. Synthesis, Characterization and DFT Calculations of 4,5,12- and 1,8,12-trichloro-9,10-dihydro-9,10-ethanoanthracene-12-carbonitriles. Crystals 2017, 7, 259.

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