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Persistent antimony- and bismuth-centered radicals in solution.

Shintaro Ishida1, Fumiya Hirakawa, Ko Furukawa

  • 1Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578 (Japan). sishida@m.tohoku.ac.jp.

Angewandte Chemie (International Ed. in English)
|July 29, 2014
PubMed
Summary

Persistent stibinyl and bismuthinyl radicals were synthesized in solution. These novel antimony and bismuth radical species exhibit unique spectral properties and undergo cross-radical coupling reactions.

Keywords:
antimonybismuthdimerizationpersistent radicalspnictogens

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Area of Science:

  • Organometallic Chemistry
  • Radical Chemistry
  • Spectroscopy

Background:

  • Stibinyl and bismuthinyl radicals are key intermediates in antimony and bismuth chemistry.
  • These radicals have been historically difficult to isolate and study in condensed phases.

Purpose of the Study:

  • To synthesize and characterize persistent stibinyl and bismuthinyl radicals in solution.
  • To investigate the spectral and reactivity properties of these novel radical species.

Main Methods:

  • Facile dissociation of bulky-substituted dimers to generate radicals.
  • Nuclear Magnetic Resonance (NMR) and UV/Vis spectroscopy for characterization.
  • Thermodynamic parameter estimation for dissociation equilibria.

Main Results:

  • Successful synthesis of persistent stibinyl and bismuthinyl radicals in solution.
  • Identification of n→p (HOMO→SOMO) transition bands at 497 nm (stibinyl) and 543 nm (bismuthinyl).
  • Demonstration of cross-radical coupling reactions with nitroxyl radicals, yielding products in good yields.

Conclusions:

  • The study provides a viable method for generating and stabilizing elusive antimony and bismuth radicals.
  • These persistent radicals open new avenues for exploring the chemistry of p-block element radicals.
  • The observed reactivity highlights their potential as building blocks in synthesis.