Regioselective CF functionalization of ScN@(5)-C.

We report the first synthesis and computational study of ScN@C(CF) - an analog of the previously reported ScN@C(CF) with a less common carbon cage whose chemical properties presently remain far less studied. ScN@C appears to be considerably more reactive toward CF addition than ScN@C and somewhat more reactive than C. Even though the less symmetric (5)-C carbon cage offers far broader opportunities for isomerism than -C, CF addition to ScN@C proceeds regioselectively, similarly to other common fullerene reactions. A DFT survey of the thermodynamic and kinetic aspects of CF addition demonstrates that the regioselectivity is controlled kinetically.