To better understand the mechanistic pathway of proton coupled electron transfer reactions, the electrochemistry of 2,3,5,6-tetramethylphenylenediamine (H2PD) is being studied in acetonitrile, in the presence of substituted N,N-dimethylbenzamide with varying hydrogen bonding strengths. H2PD undergoes two reversible oxidations in acetonitrile, first to a radical cation (H2PD+), and then to a dication (H2PD2+).   As H2PD is oxidized, it transitions from being basic, and interacting with acids, to being acidic and interacting with bases.  The amides used in this study are very weak bases and should not be able to deprotonate H2PD2+.  Therefore any effects are likely due to hydrogen bonding alone. UV-Vis and CV simulations will be used to verify the results.

Effects of amide hydrogen bonds on the aprotic electrochemistry of 2,3,5,6- tramethylphenylene-diamine

243rd National Meeting (2012)

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