European Journal of Chemistry

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

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Muthana Abduljabbar Shanshal
Qhatan Adnan Yusuf

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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