Functionalization of fullerene via the Bingel reaction with α-chlorocarbanions: an ONIOM approach.

Two-layer ONIOM method at the ONIOM(B3LYP/6-31G(d):PM6) level of theory was applied to study the cycloaddition reaction of α-chlorocarbanions (CR2Cl(─), where R is H, Cl, CH3 CN, and NO2) and fullerene. The results show that the reaction pathways depend on the electron withdrawing functional groups or the electron donating functional groups contained in the α-chlorocarbanions. The energy profile analysis reveals that functionalization of fullerene by CCl3 (─), C(CH3)2Cl(─), and CH2Cl(─) is more favorable than by C(CN)2Cl(─) and C(NO2)2Cl(─) in terms of the thermodynamic point of view.