Abstract
Protonation of aromatic hydrocarbon radical-anions requires a change of carbon atom hybridization from the sp2 to the sp3 state. This is found to be an irreversible process, which proceeds at a fast but measurable rate. Protonation of the radical-anion from nitrogen ring systems, however, involves the nitrogen lone pair and does not require a change in hybridization. The nitrogen center in the parent compound is also hydrogen bonded to any proton donors in solution. As a consequence, protonation of nitrogen ring radical-anions by available donors is often synchronous with electron transfer to the parent molecule. Most effort over the electrochemical reduction of benzene hydrocarbons has centered on finding a reaction medium, which is also a better solvent for a substrate than liquid ammonia. Aliphatic amines have proved useful solvents, and they may be used in an undivided electrochemical cell.
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