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

Muthana Abduljabbar Shanshal; Qhatan Adnan Yusuf

doi:10.5155/eurjchem.10.4.403-408.1889

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Published: Dec 31, 2019

DOI: https://doi.org/10.5155/eurjchem.10.4.403-408.1889

Keywords:

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

Section

Research Article

Issue

Vol. 10 No. 4 (2019): December 2019

Dates

Received 2019-05-07
Accepted 2019-09-27
Published 2019-12-31

Muthana Abduljabbar Shanshal

Department of Chemistry, College of Science, University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq

http://orcid.org/0000-0001-6721-4001

Qhatan Adnan Yusuf

Department of Chemistry, College of Science, University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq

http://orcid.org/0000-0002-7053-3254

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.

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Shanshal, M. A.; Yusuf, Q. A. C-C and C-H Bond Cleavage Reactions in Acenaphthylene Aromatic Molecule, an Ab-Initio Density Functional Theory Study. Eur. J. Chem. 2019, 10, 403-408.

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