Web of Science (Emerging Sources Citation Index)

Document Type: Original Research Article

Authors

Department of Chemistry, Faculty of Basic Science, Ayatollah Boroujerdi University, Boroujerd 69199-69411, Iran

Abstract

A theoretical study at the levels of CAM-B3LYP and MP2 was reported, with the aim of understanding the possibility of functionalization of the C20 fullerene with pyridine and pyrimidine via a cycloaddition reaction. For this purpose, several [2+2] and [4+2] cycloaddition reactions were considered between C20 and pyridine or pyrimidine, and their thermodynamic and kinetic parameters were calculated. The results indicated that those [4+2] cycloaddition reactions are favorable in which the fullerene plays the role of a dienophile. It was also found that a [4+2] reaction path in which takes place via formation of two new C–C bonds between two fragments, C20 and heterocycle, is more favorable than that occurring via formation of two different bonds, C-C and C–N. The calculation of global electron density transfer (GEDT) and molecular electrostatic potential map (MESP) revealed that the transition states are relatively polar and the C20 fullerene acts as an electron acceptor. Determination of Frontier Effective-for-Reaction Molecular Orbitals (FERMOs) relevant to pyridine and pyrimidine, described satisfactorily the reactivity of different active sites of pyridine and pyrimidine. Finally, the calculation of the reactions synchronicity showed that the reactions are relatively synchronous.

Graphical Abstract

Keywords

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