Quantum chemical study of the reactivity of C60HR and C60(CHR) derivatives

In the present work a quantum chemical study of a series of substituted hydrofullerenes, C(60)HR, and a series of methanofullerenes, C(60)(CHR), is presented. Their reactivity and geometrical, energetic, electronic, and magnetic properties, as well as the influence of the substituent, are discussed. As a probe of the reactivity, the acidic properties of these fullerene derivatives were predicted, based on the calculated deprotonation energies, with a previously set up scheme. The electronic delocalization upon deprotonation was described, and the global (magnetizabilities) and local aromaticity (nucleus-independent chemical shifts) was analyzed and compared with respect to the group properties for the series of functional groups. The geometries of both acidic and basic forms were fully optimized at the AM1 level, and all property calculations were performed at the HF/3-21G and the B3LYP/6-31G* level of theory.