Redox potential inversion by ionic hydrogen bonding between phenylenediamines and pyridines

  • Chung Y
  • Tu Y
  • Lu S
 et al. 
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In electrochemical oxidations, the second oxidation potential of phenylenediamines (PD) varies because of hydrogen-bonding formation for PD(+•) with pyridines. A linear relationship was obtained for the potential shift as a function of pK(a) of the protonated pyridines and potential inversion could be observed. The oxidized PD(+•) could also form hydrogen bonding with alcohols and the shift of potential exhibits a different pattern.

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