Study of tautomerism and solvatochromism of 5-(substituted phenylazo)-3-cyano-6-hydroxy-4-methyl-2-pyridones

Jelena Lađarević; Bojan  Božić; Dušan Mijin; Luka Matović; Nataša Valentić; Evica Ivanović; Nebojša Banjac

doi:10.62638/ZasMat1394

Authors

Jelena Lađarević Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia Author https://orcid.org/0000-0002-5554-7295
Bojan Božić Institute of Physiology and Biochemistry “Ivan Djaja“, Faculty of Biology, University of Belgrade, Belgrade, Serbia Author https://orcid.org/0000-0001-9910-2741
Dušan Mijin Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia Author https://orcid.org/0000-0001-5691-2971
Luka Matović Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia, Author https://orcid.org/0000-0003-4945-7776
Nataša Valentić Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia Author https://orcid.org/0000-0002-5466-7738
Evica Ivanović Faculty of Agriculture, University of Belgrade, Belgrade, Serbia Author https://orcid.org/0000-0002-5055-4568
Nebojša Banjac Faculty of Agriculture, University of Belgrade, Belgrade, Serbia Author https://orcid.org/0000-0002-4359-6276

DOI:

https://doi.org/10.62638/ZasMat1394

Abstract

In this study, ten 5-(substituted phenylazo)-3-cyano-6-hydroxy-4-methyl-2-pyridone dyes were synthesized, differing in both the position and the nature of substituents on the phenyl ring. The structural characterization of the dyes was performed using melting point analysis, FT-IR, NMR, and UV-Vis spectroscopy. The study includes spectral determination of the possible tautomeric forms in both the solid state and various solvents. Solvatochromic properties are investigated in 21 solvents with varying properties to assess the impact of solvent-solute interactions and effects of substituents electronic nature on the absorption maxima. For quantitative evaluation of the non-specific and specific solvent effects on the UV-Vis absorption maxima, the principles of the linear solvation energy relationships are used, i.e. models proposed by Kamlet-Taft and Catalán. Based on electronic distribution and substituent effects, methoxy-substituted dyes in ortho- and para- positions of phenyl ring have emerged as the most promising candidates for corrosion inhibition.

Keywords:

pyridone azo dyes, tautomerism, hydrazone, LSER

Supporting Agencies

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

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