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Crystals 2017, 7(9), 259; doi:10.3390/cryst7090259

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

1
Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
2
Department of Chemistry, Rabigh College of Science and Art, P.O. Box 344, Rabigh 21911, Saudi Arabia
3
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, 21321 Alexandria, Egypt
4
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
5
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)
View Full-Text   |   Download PDF [3299 KB, uploaded 25 August 2017]   |  

Abstract

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
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MDPI and ACS Style

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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