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Related Experiment Videos

L-shaped three-center two-electron (C-C-C)+ bonding array.

Naohiko Yoshikai1, Salai Cheettu Ammal, Eiichi Nakamura

  • 1Contribution from the Department of Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan.

Journal of the American Chemical Society
|October 8, 2004
PubMed
Summary

Quantum mechanical calculations reveal new L-shaped carbenium ion complexes with alkynes. This "open" three-center, two-electron bonding is significant for alkyl carbenium ions.

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Area of Science:

  • Quantum Chemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • Carbenium ions are key intermediates in organic reactions.
  • Understanding their interactions with unsaturated hydrocarbons is crucial.
  • Previous studies have focused on linear or bridged structures.

Purpose of the Study:

  • To investigate the structures and reactivity of carbenium ion complexes with acetylene and propyne.
  • To explore novel bonding geometries beyond conventional vinyl cations.
  • To characterize the electronic and geometric features of these complexes.

Main Methods:

  • Electron-correlated quantum mechanical calculations were employed.
  • Hybrid density functional theory was utilized.
  • Perturbation theory and coupled cluster methods were applied for high accuracy.

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Main Results:

  • Two main structures were identified: an "open" 3c-2e structure and a conventional vinyl cation.
  • The "open" 3c-2e structure, with an L-shaped carbon framework, was found to be a stable minimum.
  • This novel bonding geometry is prevalent for methyl and various alkyl carbenium ions.

Conclusions:

  • A new type of "open" three-center, two-electron bonding in carbenium ion-alkyne complexes has been characterized.
  • The L-shaped geometry represents a significant deviation from previously known structures.
  • This finding expands the understanding of bonding in carbocation chemistry.