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Original Articles

Stone-Wales Rearrangement as the Double Olefin-Carbene 1,2-CC Bond Shift. Denied Role of Triplet Biradicals

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Pages 259-270 | Received 20 Oct 1997, Published online: 23 Apr 2008

References

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  • Honda , K. and Osawa , E. 1996 . Fullerene Sci. Technol. , 4 : 925 To be more precise, the energy of transition state of C60 corresponding to b in Scheme 2 was 166.6 kcal/mol and that of d 172.5 kcal/mol relative to a (Ih-C60). The extremely high barrier must be due, at least partly, to the outstanding stability of the reference structure. Because the fullerene rearrangement generally proceeds towards buckminsterfullerene and other stable isomers of higher fullerenes, the barrier height in this case should be computed relative to e, namely relative to the C2v penultimate intermediate, which gives 129 kcal/mol. The AMI value of 47.8 kcal/mol calculated by AMI method for the energy difference between Ih-C60 and C2v-C60 compares well with the estimates obtained by other methods of calculation: 37 kcal/mol by LDF (Yi, J.-Y., and Bernholc, J. J. Chem. Phys. 1992, 96, 8634), 49 kcal/mol by HF/3-21G (Raghavachari, K., and Rohlfing, C. M. J. Phys. Chem. 1992 96, 2463), and 44 kcal/mol by MNDO (ref. 17)
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