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Related Experiment Videos

Sterically crowded bicyclo[1.1.0]butane radical cations.

Nicolas J Saettel1, Olaf Wiest

  • 1Department of Chemistry and Biochemistry, University of Notre Dame, Indiana 46556-5670, USA.

The Journal of Organic Chemistry
|May 24, 2003
PubMed
Summary

Sterically crowded bicyclo[1.1.0]butanes and their radical cations show how steric and electronic effects influence carbon-carbon single bond length. Substitution modulates bond character, making these compounds promising for studying extremely long carbon-carbon bonds.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Physical Chemistry

Background:

  • Carbon-carbon single bonds are fundamental in organic chemistry.
  • Understanding factors influencing C-C bond length, such as steric and electronic effects, is crucial.
  • Bicyclo[1.1.0]butanes offer a unique strained system to study these effects.

Purpose of the Study:

  • To investigate the variability of carbon-carbon single bonds in sterically crowded bicyclo[1.1.0]butanes and their radical cations.
  • To probe the interplay of steric and electronic effects on C-C bond weakening and breaking.
  • To explore the potential of these systems for creating and studying extremely long C-C single bonds.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed.

Related Experiment Videos

  • Steric and electronic effects were systematically varied through substitution at bridgehead and geminal positions.
  • The electronic and structural properties of bicyclo[1.1.0]butane radical cations were analyzed.

    • Main Results:

    • Bridgehead substitution elongated the central C-C bond.
    • Geminal substitution shortened the central C-C bond, attributed to the Thorpe-Ingold effect.
    • Substitution and electron transfer modulated the central bond character over a 0.35 Å range, without inducing ring planarization.

    Conclusions:

    • Sterically crowded bicyclo[1.1.0]butane radical cations exhibit tunable C-C bond lengths.
    • These systems are promising platforms for experimental and theoretical investigations of unusually long carbon-carbon single bonds.
    • The study highlights the significant influence of steric and electronic factors on C-C bond properties within strained ring systems.