European Journal of Chemistry

Reaction paths and transition states of the C-C and C-H bond cleavage in the aromatic anthracene and phenanthrene molecules



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Muthana Abduljabbar Shanshal
Muntadhar Abdulbary Al-Yassiri
Qhatan Adnan Yusof

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.


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Shanshal, M. A.; Al-Yassiri, M. A.; Yusof, Q. A. 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, 166-175.

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University of Baghdad, Jadirriya, Baghdad, 00964-01, Iraq
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