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Related Experiment Videos

Isolating benzenium ion salts.

Christopher A Reed1, Kee-Chan Kim, Evgenii S Stoyanov

  • 1Department of Chemistry, University of California, Riverside, California 92521-0403, USA. chris.reed@ucr.edu

Journal of the American Chemical Society
|February 13, 2003
PubMed
Summary
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Arenium ions, like protonated benzene, are now stable crystalline salts, not just transient intermediates. These stable arenium ion salts can be used as reagents in chemical reactions.

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Arenium ions are typically unstable intermediates in chemical reactions.
  • Previous studies were limited to low temperatures and superacidic conditions.

Purpose of the Study:

  • To synthesize and characterize stable arenium ion salts.
  • To investigate the properties and reactivity of these novel compounds.

Main Methods:

  • Protonation of aromatic compounds (benzene, toluene, xylenes, mesitylene, hexamethylbenzene) using carborane superacids.
  • Characterization using elemental analysis, X-ray crystallography, NMR, and IR spectroscopy.
  • Density functional theory calculations for structural and vibrational analysis.

Main Results:

Related Experiment Videos

  • Stable crystalline salts of the type [H(arene)][carborane] were successfully prepared and isolated.
  • These salts exhibit thermal stability up to >150°C.
  • Solid-state NMR spectra indicate lattice interactions are comparable to solution solvation effects.
  • Weak ion pairing between arenium cations and carborane anions was observed.
  • Arenium ions were successfully used to determine the basicity of C(60).

    • Conclusions:

    • Arenium ions can be stabilized as crystalline salts, transitioning from transient intermediates to isolable reagents.
    • The stability and characterization of these salts provide new insights into arenium ion chemistry.
    • This work opens avenues for utilizing arenium ions in broader chemical applications and reactivity studies.