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Quinoline Triradicals: A Reactivity Study.

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Protonated quinoline triradicals react with dimethyl disulfide via a novel two-step mechanism, involving proton transfer then hydrogen atom abstraction, forming abundant dimethyl disulfide radical cations.

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Area of Science:

  • Physical Chemistry
  • Organic Chemistry
  • Mass Spectrometry

Background:

  • Protonated quinoline-based radicals are key intermediates in various chemical processes.
  • Understanding their gas-phase reactivity is crucial for reaction mechanism elucidation.

Purpose of the Study:

  • To investigate the gas-phase reaction mechanism of protonated quinoline-based mono-, bi-, and triradicals with dimethyl disulfide (DMDS).
  • To elucidate the unexpected formation of abundant DMDS radical cations from triradicals.

Main Methods:

  • Gas-phase reactivity studies using a linear quadrupole ion trap mass spectrometer.
  • Quantum chemical calculations to support proposed mechanisms.
  • Studies using deuterated and methylated triradicals.

Main Results:

  • Mono- and biradicals showed expected thiomethyl abstraction.
  • Triradicals unexpectedly produced abundant DMDS radical cations.
  • A novel two-step mechanism involving proton transfer and subsequent hydrogen atom abstraction was proposed and supported.

Conclusions:

  • The reaction mechanism for triradicals differs significantly from mono- and biradicals.
  • Proton transfer followed by hydrogen atom abstraction explains the observed product distribution.
  • Radical properties like proton affinity and electron affinity govern the reaction pathway.