European Journal of Chemistry 2016, 7(2), 166-175 | doi: https://doi.org/10.5155/eurjchem.7.2.166-175.1364 | Get rights and content






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Reaction paths and transition states of the C-C and C-H bond cleavage in the aromatic anthracene and phenanthrene molecules


Muthana Abduljabbar Shanshal (1,*) , Muntadhar Abdulbary Al-Yassiri (2) , Qhatan Adnan Yusof (3)

(1) Department of Chemistry, College of Science, University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq
(2) Department of Chemistry, College of Science, University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq
(3) Department of Chemistry, College of Science, University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq
(*) Corresponding Author

Received: 11 Nov 2015 | Accepted: 06 Feb 2016 | Published: 30 Jun 2016 | Issue Date: June 2016

Abstract


The reaction paths of the C-C and C-H bond cleavage in the anthracene and phenanthrene aromatic molecules are studied by applying the ab-initio DFT method. It is found that the C-C bond cleavage proceeds via a singlet aromatic transition state, compelled through a disrotatoric ring opening reaction. A suprafacial H atom shift follows the transition state, leading to the formation of a methylene -CH2 and an acetylenic or allenic moiety. The calculated activation energies for anthracene range from 158.81-208.90 kcal/mol and the reaction energies from 96.106-156.976 kcal/mol. For phenanthrene, the energy values are 157.39-202.34 kcal/mol and 62.639-182.423 kcal/mol, respectively. For the C-H cleavage reactions, the calculated reaction energies for all C-H bonds in both molecules are almost similar, 116-117 kcal/mol. The activation energy values for anthracene and phenanthreneare 149.75-161.27 and 161.24-163.00 kcal/mol, respectively.


Keywords


DFT; B3LYP; Anthracene; Phenanthrene; Reaction paths; C-C and C-H bond cleavage

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DOI: 10.5155/eurjchem.7.2.166-175.1364

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Funding information


University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq

Citations

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[1]. Muthana Abduljabbar Shanshal, Qhatan Adnan Yusuf
C-C and C-H bond cleavage reactions in the chrysene and perylene aromatic molecules: An ab-initio density functional theory study
European Journal of Chemistry  8(3), 288, 2017
DOI: 10.5155/eurjchem.8.3.288-292.1561
/


[2]. Muthana Abduljabbar Shanshal, Qhatan Adnan Yusuf
C-C and C-H bond cleavage reactions in acenaphthylene aromatic molecule, an ab-initio density functional theory study
European Journal of Chemistry  10(4), 403, 2019
DOI: 10.5155/eurjchem.10.4.403-408.1889
/


References

[1]. Shanshal, M.; Hadi, H. Proceeding of the 6thJordanien International Conference of Chemistry, Irbid, Jordan, 2011.

[2]. Shanshal, M.; Hadi, H, Jordan J. Chem. 2012, 7, 329-337.

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

[4]. Shanshal, M.; Muala, M. M. Jordan J. Chem. 2013, 8, 113-124.

[5]. Shanshal, M.; Muala, M. M.; Al-Yassiri, M. A. Jordan J. Chem. 2013, 8, 213-224.

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

[7]. Dewar, M. J. S. The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill, N. York, 1969, pp. 169-190.

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

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

[10]. Guerrin, M. R. Energy Sources of Polycyclic Aromatic Hydrocarbons, in Polycyclic Hydrocarbons and Cancer, Academic Press Inc. N. York, 1978.

[11]. Luch, A. The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons, Imperial College Press, Singapore, 2005.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[26]. 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. Gaussian, Inc. Pittsburgh, PA, 2003.

[27]. MOLEK-9000 (ISKA-Bensheim) program package, developed by P. Bischof, UniversitatHeidelberg, and by ISKA, Bensheim.

How to cite


Shanshal, M.; Al-Yassiri, M.; Yusof, Q. Eur. J. Chem. 2016, 7(2), 166-175. doi:10.5155/eurjchem.7.2.166-175.1364
Shanshal, M.; Al-Yassiri, M.; Yusof, Q. Reaction paths and transition states of the C-C and C-H bond cleavage in the aromatic anthracene and phenanthrene molecules. Eur. J. Chem. 2016, 7(2), 166-175. doi:10.5155/eurjchem.7.2.166-175.1364
Shanshal, M., Al-Yassiri, M., & Yusof, Q. (2016). Reaction paths and transition states of the C-C and C-H bond cleavage in the aromatic anthracene and phenanthrene molecules. European Journal of Chemistry, 7(2), 166-175. doi:10.5155/eurjchem.7.2.166-175.1364
Shanshal, Muthana, Muntadhar Abdulbary Al-Yassiri, & Qhatan Adnan Yusof. "Reaction paths and transition states of the C-C and C-H bond cleavage in the aromatic anthracene and phenanthrene molecules." European Journal of Chemistry [Online], 7.2 (2016): 166-175. Web. 24 Oct. 2020
Shanshal, Muthana, Al-Yassiri, Muntadhar, AND Yusof, Qhatan. "Reaction paths and transition states of the C-C and C-H bond cleavage in the aromatic anthracene and phenanthrene molecules" European Journal of Chemistry [Online], Volume 7 Number 2 (30 June 2016)

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DOI Link: https://doi.org/10.5155/eurjchem.7.2.166-175.1364

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