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






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.7.2.166-175.1364

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 566 times | PDF Article downloaded 175 times

Funding information


University of Baghdad, Jadirriya, 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, 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. 23 Jan. 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)

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

| | | | |

| | | | | |

Save to Zotero Save to Mendeley

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

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.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort