Surprisingly long-lived ascorbyl radicals in acetonitrile: concerted proton-electron transfer reactions and thermochemistry.

@article{Warren2008SurprisinglyLA,
  title={Surprisingly long-lived ascorbyl radicals in acetonitrile: concerted proton-electron transfer reactions and thermochemistry.},
  author={Jeffrey J. Warren and James M Mayer},
  journal={Journal of the American Chemical Society},
  year={2008},
  volume={130 24},
  pages={7546-7}
}
Proton-coupled electron transfer (PCET) reactions and thermochemistry of 5,6-isopropylidene ascorbate (iAscH-) have been examined in acetonitrile solvent. iAscH- is oxidized by 2,4,6-tBu3C6H2O. and by excess TEMPO. to give the corresponding 5,6-isopropylidene ascorbyl radical anion (iAsc.-), which persists for hours at 298 K in dry MeCN solution. The stability of iAsc.- is surprising in light of the transience of the ascorbyl radical in aqueous solutions and is due to the lack of the protons… CONTINUE READING
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