Chemistry of the Fullerenes: The Manifestation of Strain in a Class of Continuous Aromatic Molecules

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Science  17 Sep 1993:
Vol. 261, Issue 5128, pp. 1545-1550
DOI: 10.1126/science.261.5128.1545


Within the wr-orbital axis vector theory, the total rehybridization required for closure of the fullerenes is approximately conserved. This result allows the development of a structure-based index of strain in the fullerenes, and it is estimated that about 80 percent of the heat of formation of the carbon atoms in C60 may be attributed to a combination of v strain and steric inhibition of resonance. Application of this analysis to the geometries of structurally characterized organometallic derivatives of C60 and C70 shows that the reactivity exhibited by the fullerenes may be attributed to the relief of a combination of local and global strain energy. C60 is of ambiguous aromatic character with anomalous magnetic properties but with the reactivity of a continuous aromatic molecule, moderated only by the tremendous strain inherent in the spheroidal structure.