C-C and C-H bond cleavage reactions in acenaphthylene aromatic molecule,  an ab-initio density functional theory study

Muthana Abduljabbar Shanshal; Qhatan Adnan Yusuf

doi:10.5155/eurjchem.10.4.403-408.1889

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Published: Dec 31, 2019

DOI: https://doi.org/10.5155/eurjchem.10.4.403-408.1889

Keywords:

DFT, B3LYP, Ab initio, Reaction paths, Acenaphthylene, C-C and C-H bond cleavage

Section

Research Article

Issue

Vol. 10 No. 4 (2019): December 2019

Dates

Received 2019-05-07
Accepted 2019-09-27
Published 2019-12-31

Muthana Abduljabbar Shanshal

Department of Chemistry, College of Science, University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq

http://orcid.org/0000-0001-6721-4001

Qhatan Adnan Yusuf

Department of Chemistry, College of Science, University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq

http://orcid.org/0000-0002-7053-3254

Abstract

The ab-initio DFT method (B3LYP) is applied to the study of the C-C and C-H bond cleavage reactions in acenaphthylene molecule. It is found that the C-C bond cleavage proceeds via a singlet aromatic transition state, compelled through a disrotatoric ring opening reaction. A sigmatropic H atom shift follows the transition state in some of these reactions, where the formation of a methylene -CH₂,acetylenyl-, allenyl- or butadienyl moiety in the final product is possible. The calculated activation and reaction energies for the C-C ring opening are 164-236 and 52-193 kcal/mol, respectively. The calculated cleavage reaction energies for the C-H bonds are 117-122 kcal/mol and the activation energies are 147-164 kcal/mol.

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Shanshal, M. A.; Yusuf, Q. A. C-C and C-H Bond Cleavage Reactions in Acenaphthylene Aromatic Molecule, an Ab-Initio Density Functional Theory Study. Eur. J. Chem. 2019, 10, 403-408.

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References

[1]. Ren, R. L.; Itoh, H.; Ouchi, K. Fuel 1989, 68, 58-65.
https://doi.org/10.1016/0016-2361(89)90012-4

[2]. Ninomiza, Y. D.; Suzuki, Z. Y. Fuel 2000, 79, 449-457.
https://doi.org/10.1016/S0016-2361(99)00180-5

[3]. Guerrin, M. R., Energy Sources of Polycyclic Aromatic Hydrocarbons, in Polycyclic Hydrocarbons and Cancer, Academic Press Inc. , N. York, 1978.
https://doi.org/10.1016/B978-0-12-279201-4.50008-6

[4]. Luch, A., The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons, Imperial College Press, Singapore, 2005.
https://doi.org/10.1142/p306

[5]. Frenklach, M.; Wang, H. Proc. Combust. Inst. 1991, 23, 1559-1566.
https://doi.org/10.1016/S0082-0784(06)80426-1

[6]. Frenklach, M.; Moriatry, N. W.; Brown, N. Proc. Combust Inst. 1998, 27, 1655-1661.
https://doi.org/10.1016/S0082-0784(98)80004-0

[7]. Ling, Y.; Martin, J. M. L.; Lifschitz, C. J. Phys. Chem. A 1997, 101, 219-226.
https://doi.org/10.1021/jp962584q

[8]. Mebel, A. M.; Lin, S. H; Yang, X. M.; Lee, Y. T. J. Phys. Chem A 1997, 101, 6781-6789.
https://doi.org/10.1021/jp970596l

[9]. Boehm, H.; Jander, H. Phys. Chem. Chem. Phys. 1999, 1, 3775-3781.
https://doi.org/10.1039/a903306h

[10]. May, K.; Dopperich, S.; Furda, F.; Untereiner, B. V.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2000, 2, 5084-5088.
https://doi.org/10.1039/b005595f

[11]. Untereiner, B. V.; Sierka, M.; Ahlrichs, R. Phys. Chem. Chem Phys. 2004, 6, 4377-4384.
https://doi.org/10.1039/b407279k

[12]. Harvey, R. G., Polycyclic Aromatic Hydrocarbons; Chemistry and Carcinogenity, Cambridge University Press, Cambridge, 1991.

[13]. Harvey, R. G., Polycyclic Aromatic Hydrocarbons, Wiley-VCH, New York, 1997.

[14]. Wu, X.; Zhu, C. Chem. Rec. 2018, 18, 1-13.
https://doi.org/10.1002/tcr.201700090

[15]. Shanshal, M.; Hadi, H. Proceeding of the 6th Jordanien International Conference of Chemistry, Irbid, Jordan, 2011.

[16]. Shanshal, M.; Hadi, H. Jordan. J. Chem. 2012, 7(4), 329-337.

[17]. Shanshal, M.; Muala, M. M. Jordan. J. Chem. 2011, 6(2), 165-173.

[18]. Shanshal, M.; Muala, M. M. Jordan. J. Chem. 2013, 8(2), 113-124.
https://doi.org/10.12816/0001522

[19]. Shanshal, M; Muala, M. M.; Al-Yassiri, M. A. Jordan. J. Chem. 2013, 8(4), 213-224.
https://doi.org/10.12816/0025776

[20]. Al-Yassiri, M.; Shanshal, M. Eur. J. Chem. 2015, 6(3), 261-269.
https://doi.org/10.5155/eurjchem.6.3.261-269.1239

[21]. Shanshal, M.; Al‐Yassiri, M.; Yusof, Q. Eur. J. Chem. 2016, 7(2) 166‐175.
https://doi.org/10.5155/eurjchem.7.2.166-175.1364

[22]. Shanshal, M.; Yusuf, Q. Eur. J. Chem. 2017, 8(3), 288-292.
https://doi.org/10.5155/eurjchem.8.3.288-292.1561

[23]. Roothaan, C. C. J. Rev. Mod. Phys. 1951, 23, 69-89.
https://doi.org/10.1103/RevModPhys.23.69

[24]. Kohn, W.; Sham, L. J. Phys. Rev. A 1965, 140, 1133-1138.
https://doi.org/10.1103/PhysRev.140.A1133

[25]. Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864-871.
https://doi.org/10.1103/PhysRev.136.B864

[26]. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3001.
https://doi.org/10.1103/PhysRevA.38.3098

[27]. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
https://doi.org/10.1103/PhysRevB.37.785

[28]. Dewar, M. J. S., The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill Book Company, NewYork, 1969.

[29]. Ditchfield, R.; Hehre, W. J; Pople, J. A. J. Chem Phys. 1971, 54(2), 724-728.
https://doi.org/10.1063/1.1674902

[30]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A..; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; P. Hratchian, H.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J., Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.; Gaussian03, Gaussian Inc. Pittsburgh, PA, 2003.

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