Structure-Dependent Electrochemical Behavior of 2-Pyridone Derivatives: A Combined Experimental and Theoretical Study

In this work, the electrooxidation ability of nine pyridones was evaluated using cyclic (CV) and square-wave voltammetry (SWV) in Britton-Robinson (BR) aqueous buffer solutions on a glassy carbon electrode (GC). The dependence of electrochemical activity on pyridone structure was elucidated by means of experimentally obtained spectra and quantum chemical calculations. Firstly, it was shown that electrochemical activity is determined by the -OH group as a substituent in position 6 of the pyridone ring. By coupling the experimentally obtained UV-Vis spectra and DFT calculations, the most stable forms, both protonated and deprotonated, were defined. The calculated values are consistent with the electrochemical behavior observed, indicating that the deprotonated anionic form was the most electrochemically active. Moreover, the impact of the substituent in position 3 of the pyridone scaffold was discussed.

Automated summary

In this study, the electrooxidation ability of nine pyridones was evaluated using cyclic and square-wave voltammetry in aqueous buffer solutions. The influence of pyridone structure on electrochemical activity was investigated through experimental spectra and quantum chemical calculations. The presence of -OH group at position 6 of the pyridone ring was found to determine the electrochemical activity. The most stable forms, both protonated and deprotonated, were defined using UV-Vis spectra and DFT calculations, with the deprotonated anionic form identified as the most electrochemically active. Additionally, the impact of the substituent at position 3 of the pyridone scaffold was discussed.