Buckminsterfullerane: the inside story.

The stereoisomers of fully reduced buckminsterfullerene C(60)H(60) have been investigated with the molecular mechanics program MM3. Although it might be expected that chemical reduction would deliver all of the hydrogens to the outside, the symmetric structure produced in this way is predicted to be highly strained. Moving just one hydrogen to the inside is predicted to decrease the energy by 53 kilocalories (kcal) per mole. Putting additional hydrogens on the inside further lowers the predicted energy (depending on the steric relations between them). The miniimum energy isomer is predicted to have ten hydrogens inside with C(1) symmetry and to have an energy 400 kcal/mol less than that of the all-outside isomer. These results suggest that a process which could achieve isomerization would produce a mixture of isomers, most of which with ten hydrogens on the inside.