European Journal of Chemistry 2017, 8(3), 288-292 | doi: https://doi.org/10.5155/eurjchem.8.3.288-292.1561 | Get rights and content






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C-C and C-H bond cleavage reactions in the chrysene and perylene aromatic molecules: An ab-initio density functional theory study


Muthana Abduljabbar Shanshal (1,*) , Qhatan Adnan Yusuf (2)

(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
(*) Corresponding Author

Received: 07 Mar 2017 | Accepted: 05 Aug 2017 | Published: 30 Sep 2017 | Issue Date: September 2017

Abstract


The ab-initio DFT (B3LYP) method is applied for the study of C-C and C-H bond cleavage reactions in chrysene and perylene aromatic molecules. 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 in some of these reactions, where the formation of a methylene -CH2,acetylenyl-, allenyl- or butadienyl- moiety in the final product is possible. Activation energies are calculated for the ring opening and show the following values; for chrysene, 136.97-197.69 kcal/mol and for perylene, 160.87-187.33 kcal/mol. The reaction energies range from 95.57-162.42 kcal/mol for chrysene and 98.12-168.28 kcal/mol for perylene. The calculated cleavage reaction energies for all C-H bonds in both molecules are almost similar, 116-117 kcal/mol. Their activation energies however are different, for chrysene they range from 148.57-154.97 kcal/mol and for perylene 148.30-162.73 kcal/mol.


Keywords


DFT; B3LYP; Perylene; Chrysene; Reaction paths; C-C and C-H bond cleavage

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DOI: 10.5155/eurjchem.8.3.288-292.1561

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[1]. 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


Shanshal, M.; Yusuf, Q. Eur. J. Chem. 2017, 8(3), 288-292. doi:10.5155/eurjchem.8.3.288-292.1561
Shanshal, M.; Yusuf, Q. C-C and C-H bond cleavage reactions in the chrysene and perylene aromatic molecules: An ab-initio density functional theory study. Eur. J. Chem. 2017, 8(3), 288-292. doi:10.5155/eurjchem.8.3.288-292.1561
Shanshal, M., & Yusuf, Q. (2017). 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), 288-292. doi:10.5155/eurjchem.8.3.288-292.1561
Shanshal, Muthana, & 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 [Online], 8.3 (2017): 288-292. Web. 28 Oct. 2020
Shanshal, Muthana, AND Yusuf, Qhatan. "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 [Online], Volume 8 Number 3 (30 September 2017)

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DOI Link: https://doi.org/10.5155/eurjchem.8.3.288-292.1561

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