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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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


DFT; B3LYP; Pyrene; C-C and C-H; Bond cleavage; Reaction paths

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DOI: 10.5155/eurjchem.6.3.261-269.1239

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Funding information


University of Baghdad, 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
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[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
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[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
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How to cite


Al-Yassiri, M.; Shanshal, M. Eur. J. Chem. 2015, 6(3), 261-269. doi:10.5155/eurjchem.6.3.261-269.1239
Al-Yassiri, M.; Shanshal, M. Reaction pathways and transition states of the C-C and C-H bond cleavage in the aromatic pyrene molecule - A Density Functional study. Eur. J. Chem. 2015, 6(3), 261-269. doi:10.5155/eurjchem.6.3.261-269.1239
Al-Yassiri, M., & Shanshal, M. (2015). Reaction pathways and transition states of the C-C and C-H bond cleavage in the aromatic pyrene molecule - A Density Functional study. European Journal of Chemistry, 6(3), 261-269. doi:10.5155/eurjchem.6.3.261-269.1239
Al-Yassiri, Muntadar, & Muthana Shanshal. "Reaction pathways and transition states of the C-C and C-H bond cleavage in the aromatic pyrene molecule - A Density Functional study." European Journal of Chemistry [Online], 6.3 (2015): 261-269. Web. 23 Jan. 2020
Al-Yassiri, Muntadar, AND Shanshal, Muthana. "Reaction pathways and transition states of the C-C and C-H bond cleavage in the aromatic pyrene molecule - A Density Functional study" European Journal of Chemistry [Online], Volume 6 Number 3 (30 September 2015)

DOI Link: https://doi.org/10.5155/eurjchem.6.3.261-269.1239

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