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

Mirković, Jelena; Rogan, Jelena; Poleti, Dejan; Vitnik, Vesna D.; Vitnik, Željko J.; Ušćumlić, Gordana S.; Mijin, Dušan Ž.

doi:10.1016/j.dyepig.2014.01.007

Cited by 28 publications

(48 citation statements)

References 30 publications

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“…The favored pathway is: C5 → C4 → C3 → CN and the other one is to the C6 carbonyl group. This proposed transmission trend is in accordance with previously reported density function theory (DFT) calculation for ICT of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones [12]. On contrary, electron accepting substituents can interact with lone electron pair from hydrazone nitrogen and thus oppose extended delocalization between N H and pyridone ring.…”

Section: Lfer Analysissupporting

confidence: 90%

“…Arylazo pyridone dyes exhibit azo-hydrazone tautomerism when hydroxy group is conjugated with the azo bridge. According to the literature, azo dyes having different 3-cyano-6-hydroxy-4-methyl-2-pyridones as a coupling component exist in hydrazone form in the solid state [12]. In the solutions, depending on the dye structure and the used solvent, the equilibrium is predominantly shifted in the favor of the hydrazone form.…”

Section: Introductionmentioning

confidence: 99%

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Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones

Mirković

Božić

Mutavdžić

et al. 2014

Chemical Physics Letters

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Section: Lfer Analysissupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones

Mirković

Božić

Mutavdžić

et al. 2014

Chemical Physics Letters

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“…Therefore, the crystal data of a closely related molecule, 3-cyano-1-ethyl-6-hydroxy-4-methyl-5-(4methoxyphenylazo)-2-pyridone, from our previous paper [21], are compared with those of the title compounds. Therefore, the crystal data of a closely related molecule, 3-cyano-1-ethyl-6-hydroxy-4-methyl-5-(4methoxyphenylazo)-2-pyridone, from our previous paper [21], are compared with those of the title compounds.…”

Section: Molecular Geometrymentioning

confidence: 99%

Experimental and theoretical insight into the electronic properties of 4‐aryl‐5‐arylazo‐3‐cyano‐6‐hydroxy‐2‐pyridone dyes

Vitnik

Božić

et al. 2017

Coloration Technology

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In this paper, spectroscopic and quantum mechanical investigation of nine 4-aryl-5-arylazo-3-cyano-6hydroxy-2-pyridone dyes was performed, and obtained density functional theory (DFT) results were compared with experimental data. The structural and spectroscopic properties of azo-2-pyridone dyes were studied by DFT using B3LYP, CAM-B3LYP, and M06-2X methods with a 6-311++G(d,p) basis set. Comparison of results reveals that the scaled theoretical vibrational frequencies of azo dyes are in good agreement with experimental data. The time-dependent DFT calculated and experimental ultraviolet-visible (UV-vis) absorption spectra are also in good agreement. The effect of electron-donating -OCH 3 and electronwithdrawing -NO 2 groups on the structural parameters, vibrational frequencies, UV-vis absorption, and natural bond orbital (NBO) atomic charges were thoroughly analysed. Vibrational, UV-vis, and NBO analyses confirm that investigated dyes exist in the hydrazo tautomeric form in the solid state and ethanol solution. These analyses signify the occurrence of intramolecular charge transfer in these azo-pyridone dyes.

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“…18 Dyes 3, 4, 6, 8, 11 and 12 are described in literature. [10][11][12][19][20][21][22] The physical, analytic _________________________________________________________________________________________________________________________ (CC) 2014 SCS. All rights reserved.…”

Section: Preparation Of Arylazo Pyridone Dyesmentioning

confidence: 99%

Optimization of electrochemical decolorization of certain arylazo pyridone dyes

Mirković

Prlainović

Ušćumlić

et al. 2014

JSCS

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Electrocatalytic decolorization of arylazo pyridone dyes was investigated in the presence of sodium chloride using a DSA Ti/PtO x electrode in dilute sodium hydroxide. The decolorization could be attributed to the indirect oxidation of the investigated dyes by electrogenerated hypochlorite formed from the chloride oxidation. The electrochemical decolorization was investigated for the different sodium hydroxide concentrations in the range from 40 mg dm -3 to 4 g dm -3 , sodium chloride concentrations in the range from 15 to 40 g dm -3 , currents in the range of 100 to 250 mA and dye concentrations from 5 to 20 mg dm -3 . The optimum electrolysis conditions are suggested. The effect of substituents on the reaction rate was also studied.

show abstract

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

Cited by 28 publications

References 30 publications

Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones

Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones

Experimental and theoretical insight into the electronic properties of 4‐aryl‐5‐arylazo‐3‐cyano‐6‐hydroxy‐2‐pyridone dyes

Optimization of electrochemical decolorization of certain arylazo pyridone dyes

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