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Related Experiment Video

Updated: May 5, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Carbon's Three-Center, Four-Electron Tetrel Bond, Treated Experimentally.

Alavi Karim1, Nils Schulz2, Hanna Andersson1,3

  • 1Department of Chemistry and Molecular Biology , University of Gothenburg , SE-412 96 Gothenburg , Sweden.

Journal of the American Chemical Society
|November 29, 2018
PubMed
Summary

Researchers experimentally confirmed the strongest tetrel bond yet, a carbon-centered interaction involving a carbenium ion and a bidentate Lewis base. This discovery offers a new model for studying chemical bonding and reaction mechanisms.

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Area of Science:

  • Chemical bonding
  • Noncovalent interactions
  • Supramolecular chemistry

Background:

  • Tetrel bonding involves group IV elements interacting with electron donors.
  • It is a directional interaction, similar to hydrogen and halogen bonding, but less explored.
  • Understanding tetrel bonds is crucial for advancing chemical bonding theories.

Purpose of the Study:

  • To experimentally investigate a novel carbon-centered tetrel bond, [N-C-N]+.
  • To characterize the structure and stability of this tetrel bond complex.
  • To compare this tetrel bond with analogous halogen bonds and explore factors influencing its formation.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy
  • Titration calorimetry
  • Reaction kinetics studies
  • Crystallography

Main Results:

  • Experimental evidence for the existence and structure of the [N-C-N]+ tetrel bond was obtained.
  • This represents the strongest tetrel bond reported to date.
  • Bidentate Lewis bases stabilize the tetrel bond, while monodentate bases induce reactions.

Conclusions:

  • The study confirms a strong, experimentally validated carbon-centered tetrel bond.
  • The findings highlight the importance of Lewis base denticity in stabilizing tetrel bonds.
  • The observed complex geometry serves as a model for SN2 transition states, aiding reaction mechanism studies.