Theoretical Determination of the Active Sites of Naphthalene, Nitronaphthalene, Methoxynaphthalene, Quinoline and Isoquinoline in Cycloaddition Reaction with C20 Fullerene

Document Type : Research Article


Chemistry Department, Faculty of Basic Science, Ayatollah Boroujerdi University, Boroujerd,, I.R. IRAN


In this research, a theoretical study on the cycloaddition reaction of the C20 fullerene and certain fused bicyclic aromatic compounds including naphthalene, 2-methoxynaphthalene, 2-nitronaphthalene, quinoline, and isoquinoline was carried out with the aims of functionalization possibility of the fullerene and investigation of the reactivity and regioselectivity. For this purpose, the [4+2] cycloaddition reaction between the above mentioned aromatic systems and fullerene was studied in which, the fullerene and aromatic systems act as dienophile and diene, respectively. Except for the naphthalene, two possible reaction paths were considered for the aromatic systems in which, the substituent- or heteroatom-containing ring reacts in one path and the ring without substituent or heteroatom reacts in another one. The thermodynamic and kinetic parameters of each reaction path were calculated using optimization of the reactants, products, and transition states geometries. In order to study the reactivity of different positions of the naphthalene, 2-nitronaphthalene, 2-methoxynaphthalene, quinoline, and isoquinoline, three different methods were used including calculation of the Parr as well as Fukui functions and the value of the contribution of different atoms in the HOMO of the aromatic system. The results indicated that the Fukui functions can completely describe the reactivity of different positions of the above aromatic compounds. Also, the Parr functions and the contribution value of different atoms in HOMO can satisfactorily describe the reactivities in the corresponding cycloaddition reactions. The Global Electron Density Transfer (GEDT) value was also calculated for the reactions and the results revealed that the reactions are polar in character and the electron density is transferred from the aromatic compound toward the fullerene. Finally, the calculation of the synchronicity showed that the reactions of fullerene with the naphthalene and the heteroatom-containing ring in the quinoline and isoquinoline are more synchronous in comparison to the other ones.


Main Subjects

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