CER - Central Repository
Institute of Chemistry, Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   CER
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
  •   CER
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

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
Mirkovic, Jelena
Rogan, Jelena R.
Poleti, Dejan
Vitnik, Vesna
Vitnik, Željko
Ušćumlić, Gordana
Mijin, Dušan
Article (Published version)
Metadata
Show full item record
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:
  • 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)
  • HP-SEE European project

DOI: 10.1016/j.dyepig.2014.01.007

ISSN: 0143-7208

WoS: 000332051200022

Scopus: 2-s2.0-84893147963
[ Google Scholar ]
24
22
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1509
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
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 . .

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

re3dataOpenAIRERCUB
 

 

All of DSpaceInstitutions/communitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

re3dataOpenAIRERCUB