European Journal of Chemistry 2019, 10(4), 403-408 | doi: https://doi.org/10.5155/eurjchem.10.4.403-408.1889 | Get rights and content

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C-C and C-H bond cleavage reactions in acenaphthylene aromatic molecule, an ab-initio density functional theory study


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

(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 May 2019 | Revised: 22 Sep 2019 | Accepted: 27 Sep 2019 | Published: 31 Dec 2019 | Issue Date: December 2019

Abstract


The ab-initio DFT method (B3LYP) is applied to the study of the C-C and C-H bond cleavage reactions in acenaphthylene molecule. It is found that the C-C bond cleavage proceeds via a singlet aromatic transition state, compelled through a disrotatoric ring opening reaction. A sigmatropic 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. The calculated activation and reaction energies for the C-C ring opening are 164-236 and 52-193 kcal/mol, respectively. The calculated cleavage reaction energies for the C-H bonds are 117-122 kcal/mol and the activation energies are 147-164 kcal/mol.


Keywords


DFT; B3LYP; Ab initio; Reaction paths; Acenaphthylene; C-C and C-H bond cleavage

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DOI: 10.5155/eurjchem.10.4.403-408.1889

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[1]. Mohammad Suhail, Sofi Danish Mukhtar, Imran Ali, Ariba Ansari, Saiyam Arora
Theoretical DFT study of Cannizzaro reaction mechanism: A mini perspective
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DOI: 10.5155/eurjchem.11.2.139-144.1975
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How to cite


Shanshal, M.; Yusuf, Q. Eur. J. Chem. 2019, 10(4), 403-408. doi:10.5155/eurjchem.10.4.403-408.1889
Shanshal, M.; Yusuf, Q. C-C and C-H bond cleavage reactions in acenaphthylene aromatic molecule, an ab-initio density functional theory study. Eur. J. Chem. 2019, 10(4), 403-408. doi:10.5155/eurjchem.10.4.403-408.1889
Shanshal, M., & Yusuf, Q. (2019). 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), 403-408. doi:10.5155/eurjchem.10.4.403-408.1889
Shanshal, Muthana, & 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 [Online], 10.4 (2019): 403-408. Web. 5 Mar. 2021
Shanshal, Muthana, AND Yusuf, Qhatan. "C-C and C-H bond cleavage reactions in acenaphthylene aromatic molecule, an ab-initio density functional theory study" European Journal of Chemistry [Online], Volume 10 Number 4 (31 December 2019)

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European Journal of Chemistry 2019, 10(4), 403-408 | doi: https://doi.org/10.5155/eurjchem.10.4.403-408.1889 | Get rights and content

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