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Int. J. Mol. Sci. 2015, 16(3), 5271-5284; doi:10.3390/ijms16035271

Mechanistic Studies on the Dibenzofuran Formation from Phenanthrene, Fluorene and 9–Fluorenone

Environment Research Institute, Shandong University, Jinan 250100, China
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Author to whom correspondence should be addressed.
Academic Editor: Christo Christov
Received: 2 February 2015 / Revised: 2 March 2015 / Accepted: 4 March 2015 / Published: 6 March 2015
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)
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Abstract

We carried out molecular orbital theory calculations for the homogeneous gas‑phase formation of dibenzofuran from phenanthrene, fluorene, 9-methylfluorene and 9-fluorenone. Dibenzofuran will be formed if ∙OH adds to C8a, and the order of reactivity follows as 9-fluorenone > 9-methylfluorene > fluorene > phenanthrene. The oxidations initiated by ClO∙ are more favorable processes, considering that the standard reaction Gibbs energies are at least 21.63 kcal/mol lower than those of the equivalent reactions initiated by ∙OH. The adding of ∙OH and then O2 to phenanthrene is a more favorable route than adding ∙OH to C8a of phenanthrene, when considering the greater reaction extent. The reaction channel from fluorene and O2 to 9-fluorenone and H2O seems very important, not only because it contains only three elementary reactions, but because the standard reaction Gibbs energies are lower than −80.07 kcal/mol. View Full-Text
Keywords: dibenzofuran; polycyclic aromatic hydrocarbons; formation mechanism; chlorine monoxide radical; density functional method dibenzofuran; polycyclic aromatic hydrocarbons; formation mechanism; chlorine monoxide radical; density functional method
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Li, S.; Zhang, Q. Mechanistic Studies on the Dibenzofuran Formation from Phenanthrene, Fluorene and 9–Fluorenone. Int. J. Mol. Sci. 2015, 16, 5271-5284.

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