Stereoelectronic effect of curved aromatic structures: Favoring the unexpected endo conformation of benzylic-substituted sumanene

Shuhei Higashibayashi, Satoru Onogi, Hemant Kumar Srivastava, G. Narahari Sastry, Yao Ting Wu, Hidehiro Sakurai

Research output: Contribution to journalArticle

24 Citations (Scopus)

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-H bond with the bowl.

Original languageEnglish
Pages (from-to)7314-7316
Number of pages3
JournalAngewandte Chemie - International Edition
Volume52
Issue number28
DOIs
Publication statusPublished - 2013 Jul 8
Externally publishedYes

Keywords

  • conformation analysis
  • density functional calculations
  • hyperconjugation
  • through-bond interactions
  • through-space interactions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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