TY  - JOUR
AU  - Mirkovic, Jelena
AU  - Božić, Bojan
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Rogan, Jelena R.
AU  - Poleti, Dejan
AU  - Ušćumlić, Gordana
AU  - Mijin, Dušan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2318
AB  - Ten 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones were studied (five new compounds) to provide insight into the electronic effects of diverse substituents located at different positions in their phenyl moieties. The structural features of these dyes were examined by combining experimental and theoretical approaches. The crystal structures of two derivatives were revealed by X-ray crystallography and diverse packing modes owing to different intermolecular interactions (- stacking and lone pair- interactions, as well as hydrogen bonds) were found. A study on lattice energy and energy related to the molecular pairs obtained from their crystal packing was performed. The tautomerism and ionisation of the dyes in ethanol or N,N -dimethylformamide solution were rationalised in terms of diazo component substitution pattern.
PB  - Blackwell Publishing Ltd
T2  - Coloration Technology
T1  - Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones
VL  - 134
IS  - 1
SP  - 33
EP  - 43
DO  - 10.1111/cote.12321
ER  - 

@article{
author = "Mirkovic, Jelena and Božić, Bojan and Vitnik, Vesna and Vitnik, Željko and Rogan, Jelena R. and Poleti, Dejan and Ušćumlić, Gordana and Mijin, Dušan",
year = "2018",
abstract = "Ten 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones were studied (five new compounds) to provide insight into the electronic effects of diverse substituents located at different positions in their phenyl moieties. The structural features of these dyes were examined by combining experimental and theoretical approaches. The crystal structures of two derivatives were revealed by X-ray crystallography and diverse packing modes owing to different intermolecular interactions (- stacking and lone pair- interactions, as well as hydrogen bonds) were found. A study on lattice energy and energy related to the molecular pairs obtained from their crystal packing was performed. The tautomerism and ionisation of the dyes in ethanol or N,N -dimethylformamide solution were rationalised in terms of diazo component substitution pattern.",
publisher = "Blackwell Publishing Ltd",
journal = "Coloration Technology",
title = "Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones",
volume = "134",
number = "1",
pages = "33-43",
doi = "10.1111/cote.12321"
}

Mirkovic, J., Božić, B., Vitnik, V., Vitnik, Ž., Rogan, J. R., Poleti, D., Ušćumlić, G.,& Mijin, D.. (2018). Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones. in Coloration Technology
Blackwell Publishing Ltd., 134(1), 33-43.
https://doi.org/10.1111/cote.12321

Mirkovic J, Božić B, Vitnik V, Vitnik Ž, Rogan JR, Poleti D, Ušćumlić G, Mijin D. Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones. in Coloration Technology. 2018;134(1):33-43.
doi:10.1111/cote.12321 .

Mirkovic, Jelena, Božić, Bojan, Vitnik, Vesna, Vitnik, Željko, Rogan, Jelena R., Poleti, Dejan, Ušćumlić, Gordana, Mijin, Dušan, "Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones" in Coloration Technology, 134, no. 1 (2018):33-43,
https://doi.org/10.1111/cote.12321 . .

TY  - JOUR
AU  - Mirkovic, Jelena
AU  - Rogan, Jelena R.
AU  - Poleti, Dejan
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Ušćumlić, Gordana
AU  - Mijin, Dušan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1509
AB  - In this work, a combined experimental and theoretical study on the structures of methoxy substituted 5-phenylazo-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones has been reported. The dyes under the investigation have been thoroughly characterized. X-ray single-crystal analysis shows that 5-(4-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone crystallizes in the hydrazone form. Quantum chemical calculations of energies, geometrical structure and vibrational wavenumbers of the investigated dyes have been performed using density functional theory. The optimized geometrical parameters obtained by density functional theory calculations are in good conformity with the single-crystal data. The fundamental vibrational wavenumbers, as well as their intensities have been calculated and a good agreement between observed and scaled calculated wavenumbers has been achieved. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital analysis. Vibrational, nuclear magnetic resonance and natural bond orbital analysis confirm that the prepared dyes exist in the hydrazone tautomeric form in the solid state and dimethyl sulfoxide solution.
PB  - Elsevier Sci Ltd, Oxford
T2  - Dyes and Pigments
T1  - On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study
VL  - 104
SP  - 160
EP  - 168
DO  - 10.1016/j.dyepig.2014.01.007
ER  - 

@article{
author = "Mirkovic, Jelena and Rogan, Jelena R. and Poleti, Dejan and Vitnik, Vesna and Vitnik, Željko and Ušćumlić, Gordana and Mijin, Dušan",
year = "2014",
abstract = "In this work, a combined experimental and theoretical study on the structures of methoxy substituted 5-phenylazo-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones has been reported. The dyes under the investigation have been thoroughly characterized. X-ray single-crystal analysis shows that 5-(4-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone crystallizes in the hydrazone form. Quantum chemical calculations of energies, geometrical structure and vibrational wavenumbers of the investigated dyes have been performed using density functional theory. The optimized geometrical parameters obtained by density functional theory calculations are in good conformity with the single-crystal data. The fundamental vibrational wavenumbers, as well as their intensities have been calculated and a good agreement between observed and scaled calculated wavenumbers has been achieved. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital analysis. Vibrational, nuclear magnetic resonance and natural bond orbital analysis confirm that the prepared dyes exist in the hydrazone tautomeric form in the solid state and dimethyl sulfoxide solution.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Dyes and Pigments",
title = "On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study",
volume = "104",
pages = "160-168",
doi = "10.1016/j.dyepig.2014.01.007"
}

Mirkovic, J., Rogan, J. R., Poleti, D., Vitnik, V., Vitnik, Ž., Ušćumlić, G.,& Mijin, D.. (2014). On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study. in Dyes and Pigments
Elsevier Sci Ltd, Oxford., 104, 160-168.
https://doi.org/10.1016/j.dyepig.2014.01.007

Mirkovic J, Rogan JR, Poleti D, Vitnik V, Vitnik Ž, Ušćumlić G, Mijin D. On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study. in Dyes and Pigments. 2014;104:160-168.
doi:10.1016/j.dyepig.2014.01.007 .

Mirkovic, Jelena, Rogan, Jelena R., Poleti, Dejan, Vitnik, Vesna, Vitnik, Željko, Ušćumlić, Gordana, Mijin, Dušan, "On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study" in Dyes and Pigments, 104 (2014):160-168,
https://doi.org/10.1016/j.dyepig.2014.01.007 . .

TY  - JOUR
AU  - Mirkovic, Jelena
AU  - Lović, Jelena
AU  - Avramov Ivić, Milka
AU  - Mijin, Dušan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1431
AB  - The electrochemical behavior of six arylazo pyridone dyes classified to the substituents present at the phenylazo and 2-pyridone moiety and their 1:1 inclusion complexes with (2-hydroxypropyl)-beta-cyclodextrin was studied using cyclic and square wave voltammetry in 0.1 M NaOH on a gold electrode. The formation of the inclusion complexes of the dyes was confirmed using UV-Vis and FTIR spectroscopy measurements. Among the studied dyes, according to potentiodynamic measurements, the most active is the dye 1. The inclusion complexes of the dyes exhibited improved electrochemical activity in comparison to the pure dyes. The results obtained by square wave voltammetry show the apparent activity of the dyes with a methoxy group as a substituent at the phenylazo moiety and ethyl and hydroxyethyl groups in the 2-pyridone moiety, and their inclusion complexes. The electrooxidation mechanism of the investigated arylazo pyridone dyes was also proposed.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Electrochimica Acta
T1  - Electrooxidative Behavior of Arylazo Pyridone Dyes and Their Inclusion Complexes on Gold Electrode in 0.1 M NaOH
VL  - 137
SP  - 705
EP  - 713
DO  - 10.1016/j.electacta.2014.06.048
ER  - 

@article{
author = "Mirkovic, Jelena and Lović, Jelena and Avramov Ivić, Milka and Mijin, Dušan",
year = "2014",
abstract = "The electrochemical behavior of six arylazo pyridone dyes classified to the substituents present at the phenylazo and 2-pyridone moiety and their 1:1 inclusion complexes with (2-hydroxypropyl)-beta-cyclodextrin was studied using cyclic and square wave voltammetry in 0.1 M NaOH on a gold electrode. The formation of the inclusion complexes of the dyes was confirmed using UV-Vis and FTIR spectroscopy measurements. Among the studied dyes, according to potentiodynamic measurements, the most active is the dye 1. The inclusion complexes of the dyes exhibited improved electrochemical activity in comparison to the pure dyes. The results obtained by square wave voltammetry show the apparent activity of the dyes with a methoxy group as a substituent at the phenylazo moiety and ethyl and hydroxyethyl groups in the 2-pyridone moiety, and their inclusion complexes. The electrooxidation mechanism of the investigated arylazo pyridone dyes was also proposed.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Electrochimica Acta",
title = "Electrooxidative Behavior of Arylazo Pyridone Dyes and Their Inclusion Complexes on Gold Electrode in 0.1 M NaOH",
volume = "137",
pages = "705-713",
doi = "10.1016/j.electacta.2014.06.048"
}

Mirkovic, J., Lović, J., Avramov Ivić, M.,& Mijin, D.. (2014). Electrooxidative Behavior of Arylazo Pyridone Dyes and Their Inclusion Complexes on Gold Electrode in 0.1 M NaOH. in Electrochimica Acta
Oxford : Pergamon-Elsevier Science Ltd., 137, 705-713.
https://doi.org/10.1016/j.electacta.2014.06.048

Mirkovic J, Lović J, Avramov Ivić M, Mijin D. Electrooxidative Behavior of Arylazo Pyridone Dyes and Their Inclusion Complexes on Gold Electrode in 0.1 M NaOH. in Electrochimica Acta. 2014;137:705-713.
doi:10.1016/j.electacta.2014.06.048 .

Mirkovic, Jelena, Lović, Jelena, Avramov Ivić, Milka, Mijin, Dušan, "Electrooxidative Behavior of Arylazo Pyridone Dyes and Their Inclusion Complexes on Gold Electrode in 0.1 M NaOH" in Electrochimica Acta, 137 (2014):705-713,
https://doi.org/10.1016/j.electacta.2014.06.048 . .