Open rather than closed malonate methano-fullerene derivatives.: The formation of methanofulleroid adducts of Y3N@C80

Cycloaddition of bromomalonates to Y3N@C-80 unexpectedly gave rise to fulleroid derivatives with unusually high stability. Complete characterization of these derivatives is described including X-ray crystallography, H-1 NMR, C-13 NMR, HMQC, UV-visible, HPLC, MALDI-MS, and electrochemistry. Density functional theory calculations are also presented, which provide a rationale for the formation of the fulleroid and reveal the underlying thermodynamic basis for their stability.