Probing concerted proton–electron transfer in phenol–imidazoles

@article{Markle2008ProbingCP,
  title={Probing concerted proton–electron transfer in phenol–imidazoles},
  author={Todd F Markle and Ian J. Rhile and A. DiPasquale and J. M. Mayer},
  journal={Proceedings of the National Academy of Sciences},
  year={2008},
  volume={105},
  pages={8185 - 8190}
}
A series of seven substituted 4,6-di-tert-butyl-2-(4,5-diarylimidazolyl)-phenols have been prepared and characterized, along with two related benzimidazole compounds. X-ray crystal structures of all of the compounds show that the phenol and imidazole rings are close to coplanar and are connected by an intramolecular ArOH⋯N hydrogen bond. One-electron oxidation of these compounds occurs with movement of the phenolic proton to the imidazole base by concerted proton–electron transfer (CPET) to… Expand
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TLDR
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