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Keywords:

  • conformation analysis;
  • density functional calculations;
  • hyperconjugation;
  • through-bond interactions;
  • through-space interactions
Thumbnail image of graphical abstract

Throwing a curve: The first example of a through-bond stereoelectronic effect for curved aromatic compounds is described for buckybowls, that is, benzylic-substituted sumanenes. Methyl- and hydroxysumanene favor the endo-R conformer because of a difference in the strength, between the conformers, of the hyperconjugation of the benzylic C[BOND]H bond with the bowl.