European Journal of Chemistry 2016, 7(2), 166-175. doi:10.5155/eurjchem.7.2.166-175.1364

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

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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[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
/


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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. 22 Sep. 2019
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

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