Direct estimate of the conjugative and hyperconjugative stabilization in diynes, dienes, and related compounds

Daniel Cappel, Sandor Tüllmann, Andreas Krapp, Gernot Frenking

Research output: Contribution to journalArticlepeer-review

84 Scopus citations

Abstract

(Equation Presented) The intrinsic strength of the conjugation and hyperconjugation in 1,3-butadiene, 1,3-butadiyne, and related compounds was determined by energy decomposition analysis. The calculations indicate that the π conjugation in 1,3-butadiyne is roughly twice as strong as that in 1,3-butadiene, and that the hyperconjugative interactions of C-H and C-C bonds with C-C multiple bonds are about half as strong as the π conjugation between multiple bonds.

Original languageEnglish
Pages (from-to)3617-3620
Number of pages4
JournalAngewandte Chemie - International Edition
Volume44
Issue number23
DOIs
StatePublished - 6 Jun 2005
Externally publishedYes

Keywords

  • Bonding analysis
  • Conjugation
  • Density functional calculations
  • Energy decomposition analysis
  • Hyperconjugation

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