Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
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.
Keywords
DOI: 10.5155/eurjchem.6.3.261-269.1239
Links for Article
| | | | |
| | | | | | |
Related Articles
Article Metrics
This Abstract was viewed 527 times |
PDF Article downloaded 188 times
Funding information
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.
How to cite
DOI Link: https://doi.org/10.5155/eurjchem.6.3.261-269.1239
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
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
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2019 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.