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
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2014
Authors
Mirkovic, JelenaRogan, Jelena R.

Poleti, Dejan

Vitnik, Vesna

Vitnik, Željko

Ušćumlić, Gordana

Mijin, Dušan

Article (Published version)

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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 calculationSource:
Dyes and Pigments, 2014, 104, 160-168Publisher:
- 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
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IHTMTY - 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 . .