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

Author:

Mašulović Aleksandra1,Lović Jelena D.2ORCID,Lađarević Jelena3ORCID,Vitnik Vesna4ORCID,Vitnik Željko4,Avramov Ivić Milka2,Mijin Dušan3ORCID

Affiliation:

1. Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia

2. Department of Electrochemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Njegoševa 12, 11000 Belgrade, Serbia

3. Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia

4. Department of Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Studentski Trg 12-16, 11000 Belgrade, Serbia

Abstract

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.

Funder

Ministry of Science, Technological Development and Innovation of the Republic of Serbia

Publisher

MDPI AG

Subject

Fluid Flow and Transfer Processes,Computer Science Applications,Process Chemistry and Technology,General Engineering,Instrumentation,General Materials Science

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