Electrochemical characterization of hydrogen-bonding complexation between indoline and nitrogen containing bases

► Mechanisms for the interaction of strong and weak bases with indoline is proposed. ► The mechanism involves H-bonding of strong bases with indoline before oxidation. ► The mechanism involves H-bonding of weak bases with oxidized indoline products. ► Linear trend between pKa of bases and shift in the oxidation onset of indoline. ► Characterization of indoline/base interaction using 1H NMR, CV and RRDE.