Oxidation behavior of N-hydroxyphthalimide (NHPI) and its electrocatalytic ability toward benzyl alcohol: Proton acceptor effect

The effect of proton acceptor on the electrochemistry of proton-coupled electron transfer reagents is always worthy of attention. Formal potentials of NHPI with different proton acceptors have been measured by cyclic voltammetry and were used to discriminate hydrogen bonding and deprotonation engaging in the oxidation of NHPI. With the negative shifting of formal potentials, the formation of hydrogen bonding complex was suggested when adding water into NHPI acetonitrile solution, a new wave caused by the addition of one pyridine base may be caused by a deprotonation process followed by a single electron transfer step. In addition, electrooxidation reactions of benzyl alcohol mediated by hydrogen bonding or deprotonation modified NHPI have been addressed and significant findings have been reported.