Computational assessment of 1,3-dipolar cycloaddition of nitrile oxides with ethene and [60]fullerene

The 1,3-dipolar cycloaddition (1,3-DC) reactions of ethene and [60]fullerene with nitrile oxides, RCNO, have been studied in the gas phase, using DFT method at the B3LYP/6-31G(d) level. Energetics, thermodynamic and kinetic parameters have been determined at room temperature so as to investigate the effect of electron-withdrawing and electron-releasing substituents attached to the nitrile oxides on the 1,3-DCs. These parameters have been interpreted in terms of group electronegativity and reactivity indices. An atypical behavior has been observed for the 1,3-DC involving FCNO as it has some pseudodiradical character.