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Reaction pathways and transition states of the C-C and C-H bond cleavage in the aromatic pyrene molecule - A Density Functional study
Muntadar Abd Al-Barri Hussain Al-Yassiri (1)
, Muthana Shanshal (2,*) (1) Department of Chemistry, College of Science, University of Baghdad, Baghdad, 00964-01, Iraq
(2) Department of Chemistry, College of Science, University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq
(*) Corresponding Author
Received: 10 Jan 2015 | Accepted: 04 Apr 2015 | Published: 30 Sep 2015 | Issue Date: September 2015
Abstract
The activation and reaction energies of the C-C and C-H bonds cleavage in pyrene molecule are calculated applying the Density Functional Theory and 6-311G Gaussian basis. Different values for the energies result for the different bonds, depending on the location of the bond and the structure of the corresponding transition states. The C-C bond cleavage reactions include H atom migration, in many cases, leading to the formation of CH2 groups and H-C≡C- acetylenic fragments. The activation energy values of the C-C reactions are greater than 190.00 kcal/mol for all bonds, those for the C-H bonds are greater than 160.00 kcal/mol. The reaction energy values for the C-C bonds range between 56.497 to 191.503 kcal/mol. As for the C-H cleavage reactions the activation energies range from 163.535 to 165.116 kcal/mol, the reaction energies are nearly constant, 117.500kcal/mol. The geometries of the transition states and reaction products are discussed too.
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DOI: 10.5155/eurjchem.6.3.261-269.1239
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University of Baghdad, Baghdad, 00964-01, Iraq
Citations
[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, 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 7(2), 166, 2016
DOI: 10.5155/eurjchem.7.2.166-175.1364
[3]. 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]. Harvey, R. G. Polycyclic Aromatic Hydrocarbons; Chemistry and Carcinogenity, Cambridge University Press, Cambridge, 1991.
[2]. Harvey, R. G. Polycyclic Aromatic Hydrocarbons, Wiley-VCH, New York, 1997.
[3]. Ren, R. L.; Itoh, H.; Ouchi, K. Fuel 1989, 68, 58-65.
http://dx.doi.org/10.1016/0016-2361(89)90012-4
[4]. Ninomiza, Y. D.; Suzuki, Z. Y. Fuel 2000, 79, 449-457.
http://dx.doi.org/10.1016/S0016-2361(99)00180-5
[5]. Guerrin, M. R. Energy Sources of Polycyclic Aromatic Hydrocarbons, in Polycyclic Hydrocarbons and Cancer, Academic Press Inc. N. York, 1978.
[6]. Luch, A. The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons, Imperial College Press, Singapore, 2005.
[7]. Frenklach, M.; Wang, H. Proc. Combust. Inst. 1991, 23, 1559-1566.
http://dx.doi.org/10.1016/S0082-0784(06)80426-1
[8]. 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
[9]. Ling, Y.; Martin, J. M. L.; Lifschitz, C. J. Phys. Chem. A 1997, 101, 219-226.
http://dx.doi.org/10.1021/jp962584q
[10]. 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
[11]. Boehm, H.; Jander, H. Phys. Chem. Chem. Phys. 1999, 1, 3775-3781.
http://dx.doi.org/10.1039/a903306h
[12]. 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
[13]. Untereiner, B. V.; Sierka, M.; Ahlrichs, R. Phys. Chem. Chem Phys. 2004, 6, 4377-4384.
http://dx.doi.org/10.1039/b407279k
[14]. Shanshal, M.; Abdullah, H. H. Proceeding of the 6thJordanien International Conference of Chemistry, Irbid, Jordan, 2011.
[15]. Shanshal, M.; Hadi, H. Jordan J. Chem. 2012, 7, 329-337.
[16]. Roothaan, C. C. J. Rev. Mod. Phys. 1951, 23(2), 69-89.
http://dx.doi.org/10.1103/RevModPhys.23.69
[17]. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133-A1138.
http://dx.doi.org/10.1103/PhysRev.140.A1133
[18]. Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864-B871.
http://dx.doi.org/10.1103/PhysRev.136.B864
[19]. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3001.
http://dx.doi.org/10.1103/PhysRevA.38.3098
[20]. Lee, C.; Yang, W. Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
http://dx.doi.org/10.1103/PhysRevB.37.785
[21]. Shanshal, M.; Muala, M. M. Jordan J. Chem. 2011, 6(2), 165-173.
[22]. Shanshal, M.; Muala, M. M. Jordan J. Chem. 2013, 8(2), 113-124.
[23]. Shanshal, M.; Muala, M. M.; Al-Yassiri, M. A. Jordan J. Chem. 2013, 8, 213-224.
[24]. Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Amer. Chem. Soc. 1995, 117, 2590-2599.
http://dx.doi.org/10.1021/ja00114a023
[25]. Laarhoven, L. J. J.; Mulder, P. J. Phys. Chem. B 1997, 101, 73-77.
http://dx.doi.org/10.1021/jp960982n
[26]. Barckholtz, C.; Barckholtz, T.; Hadad, C. M. J. Amer. Chem. Soc. 1999, 121, 492-500.
[27]. Luo, Y. R. Comprehensive Handbook of Chemical Bond Energies, CRC Press, BocaRaton, FL, 2007.
http://dx.doi.org/10.1201/9781420007282
[28]. 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.; and Pople, J. A.; Gaussian, Inc. Pittsburgh, PA, 2003.
[29]. Dewar, M. J. S. The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill, N. York, 1969, pp. 169-190.
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DOI Link: https://doi.org/10.5155/eurjchem.6.3.261-269.1239
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European Journal of Chemistry 2015, 6(3), 261-269 | doi: https://doi.org/10.5155/eurjchem.6.3.261-269.1239 | Get rights and content
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