A series of novel 5-(4-substituted phenylazo)-1-carboxymethyl-3-cyano-6-hydroxy-4-methyl-2-pyridones had been synthesized and characterized. The study includes spectral determination of the possible tautomeric forms and the intramolecular hydrogen bonding pattern. The influence of the bifurcated intramolecular hydrogen bond on the spectral properties has been discussed. The dyes exist in hydrazone form both solid state and in most of the employed solvents. Equilibrium between hydrazone and anion forms has been studied in N,N-dimethylformamide and N,N-dimethylacetamide. For quantitative elucidation of solvent effects on UV-Vis absorption maxima, a linear solvation energy relationship concept has been employed using Kamlet-Taft's and Catalan's equations. Antioxidative activity of the synthesized dyes has been chemically tested and two derivatives (hydroxy and methoxy) are qualified as promising antioxidant molecules.
Keywords:
Pyridone / Azo dye / Bifurcated bond / Intramolecular hydrogen bond / Hydrazone / Solvatochromism
TY - JOUR
AU - Lađarević, Jelena
AU - Božić, Bojan
AU - Matović, Luka
AU - Božić-Nedeljković, Biljana
AU - Mijin, Dušan
PY - 2019
UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4312
AB - A series of novel 5-(4-substituted phenylazo)-1-carboxymethyl-3-cyano-6-hydroxy-4-methyl-2-pyridones had been synthesized and characterized. The study includes spectral determination of the possible tautomeric forms and the intramolecular hydrogen bonding pattern. The influence of the bifurcated intramolecular hydrogen bond on the spectral properties has been discussed. The dyes exist in hydrazone form both solid state and in most of the employed solvents. Equilibrium between hydrazone and anion forms has been studied in N,N-dimethylformamide and N,N-dimethylacetamide. For quantitative elucidation of solvent effects on UV-Vis absorption maxima, a linear solvation energy relationship concept has been employed using Kamlet-Taft's and Catalan's equations. Antioxidative activity of the synthesized dyes has been chemically tested and two derivatives (hydroxy and methoxy) are qualified as promising antioxidant molecules.
PB - Elsevier Sci Ltd, Oxford
T2 - Dyes and Pigments
T1 - Role of the bifurcated intramolecular hydrogen bond on the physicochemical profile of the novel azo pyridone dyes
EP - 572
SP - 562
VL - 162
DO - 10.1016/j.dyepig.2018.10.058
ER -
@article{
author = "Lađarević, Jelena and Božić, Bojan and Matović, Luka and Božić-Nedeljković, Biljana and Mijin, Dušan",
year = "2019",
abstract = "A series of novel 5-(4-substituted phenylazo)-1-carboxymethyl-3-cyano-6-hydroxy-4-methyl-2-pyridones had been synthesized and characterized. The study includes spectral determination of the possible tautomeric forms and the intramolecular hydrogen bonding pattern. The influence of the bifurcated intramolecular hydrogen bond on the spectral properties has been discussed. The dyes exist in hydrazone form both solid state and in most of the employed solvents. Equilibrium between hydrazone and anion forms has been studied in N,N-dimethylformamide and N,N-dimethylacetamide. For quantitative elucidation of solvent effects on UV-Vis absorption maxima, a linear solvation energy relationship concept has been employed using Kamlet-Taft's and Catalan's equations. Antioxidative activity of the synthesized dyes has been chemically tested and two derivatives (hydroxy and methoxy) are qualified as promising antioxidant molecules.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Dyes and Pigments",
title = "Role of the bifurcated intramolecular hydrogen bond on the physicochemical profile of the novel azo pyridone dyes",
pages = "572-562",
volume = "162",
doi = "10.1016/j.dyepig.2018.10.058"
}
Lađarević, J., Božić, B., Matović, L., Božić-Nedeljković, B.,& Mijin, D.. (2019). Role of the bifurcated intramolecular hydrogen bond on the physicochemical profile of the novel azo pyridone dyes. in Dyes and Pigments
Elsevier Sci Ltd, Oxford., 162, 562-572.
https://doi.org/10.1016/j.dyepig.2018.10.058
Lađarević J, Božić B, Matović L, Božić-Nedeljković B, Mijin D. Role of the bifurcated intramolecular hydrogen bond on the physicochemical profile of the novel azo pyridone dyes. in Dyes and Pigments. 2019;162:562-572.
doi:10.1016/j.dyepig.2018.10.058 .
Lađarević, Jelena, Božić, Bojan, Matović, Luka, Božić-Nedeljković, Biljana, Mijin, Dušan, "Role of the bifurcated intramolecular hydrogen bond on the physicochemical profile of the novel azo pyridone dyes" in Dyes and Pigments, 162 (2019):562-572,
https://doi.org/10.1016/j.dyepig.2018.10.058 . .
