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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

Authorized Users Only
2014
Authors
Mirković, Jelena
Rogan, Jelena
Poleti, Dejan
Vitnik, Vesna
Vitnik, Željko
Ušćumlić, Gordana
Mijin, Dušan
Article (Published version)
Metadata
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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.

Keywords:
Pyridone / Azo dye / Azo-hydrazone tautomerism / X-ray crystallography / DFT calculation
Source:
Dyes and Pigments, 2014, 104, 160-168
Publisher:
  • Elsevier Sci Ltd, Oxford
Funding / projects:
  • HP-SEE European project
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
  • Zero- to Three-Dimensional Nanostructures for Application in Electronics and Renewable Energy Sources: Synthesis, Characterization and Processing (RS-45007)

DOI: 10.1016/j.dyepig.2014.01.007

ISSN: 0143-7208

WoS: 000332051200022

Scopus: 2-s2.0-84893147963
[ Google Scholar ]
24
22
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2768
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Mirković, Jelena
AU  - Rogan, Jelena
AU  - Poleti, Dejan
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Ušćumlić, Gordana
AU  - Mijin, Dušan
PY  - 2014
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2768
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
EP  - 168
SP  - 160
VL  - 104
DO  - 10.1016/j.dyepig.2014.01.007
UR  - conv_4364
ER  - 
@article{
author = "Mirković, Jelena and Rogan, Jelena 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",
pages = "168-160",
volume = "104",
doi = "10.1016/j.dyepig.2014.01.007",
url = "conv_4364"
}
Mirković, J., Rogan, J., 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
conv_4364
Mirković J, Rogan J, 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
conv_4364 .
Mirković, Jelena, Rogan, Jelena, 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 .,
conv_4364 .

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