The synthesis, spectroscopic properties and theoretical calculation of some novel disperse disazo dyes derived from 3-amino-5-hydroxy-1-phenylpyrazole

Karcı, Fati; Demirçalı, Aykut; Karcı, Fikret; Kara, İzzet; Ucun, Fatih

doi:10.1016/j.molstruc.2009.06.040

Cited by 25 publications

(12 citation statements)

References 51 publications

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“…The synthesized new dyes may exist in five possible tautomeric forms, i.e., keto-azo (T 1 and T 5 ), keto-hydrazo (T 2 and T 4 ) and enol-azo (T 3 ). According to the calculation results in the literature, 17,[35][36][37][38][39][40] the most stable tautomeric form is keto-hydrazo form (T 2 ) for hetarylazopyrazolone dyes. This conclusion may occur from the intramolecular O−H bond.…”

Section: Tautomerismmentioning

confidence: 99%

Synthesis, Characterization, Absorption and Fastness Properties of Novel Monoazo Dyes Derived from 1-Phenyl-3-amino-4-(2-thiazolilazo)pyrazol-5-one

Erol

2020

J. Braz. Chem. Soc.

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Monosubstitute thiazolyl amines were diazotized in acetic acid, coupled to 1-phenyl-3-aminopyrazol-5-one (1a-1c) and acetylated to obtain the 2a-2c dyes. The dyes were characterized by elemental analysis and spectroscopic (Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR), ultraviolet (UV)) methods. The effects on the visible absorption spectra of the substituents present, solvents, pH, concentration and temperature were investigated in detail. Tautomerism of the dyes were investigated by spectroscopic methods. Fastness properties of dyes were studied using the standard method for the assessment of color fastness of textile.

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Section: Tautomerismmentioning

confidence: 99%

Synthesis, Characterization, Absorption and Fastness Properties of Novel Monoazo Dyes Derived from 1-Phenyl-3-amino-4-(2-thiazolilazo)pyrazol-5-one

Erol

2020

J. Braz. Chem. Soc.

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“…The condensation of β-enaminonitriles and β-ketoesters with hydrazines continues to be the most widely used method for constructing the aminopyrazoles and pyrazolones, respectively [6,7]. The amino derivatives of pyrazoles belong to important compounds used for preparation of other functional derivatives mainly for the synthesis of condensed heterocyclic systems [8][9][10][11][12]. Also, fused pyrazoles are important compounds that have many derivatives with a wide range of interesting properties, such as antihyperglycemic, analgestic, anti-inflammatory, antipyretic, anti-bacterial, hypoglycaemic and sedative-hypnotic activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol

Patel

2012

Eur. J. Chem.

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KEYWORDSAniline derivatives were diazotized and coupled with 3-aminocrotononitrile to give the corresponding 2-arylhydrazono-3-ketiminobutyronitriles. Cyclization of these arylhydrazono derivatives with hydrazine monohydrate afforded 5-amino-4-arylazo-3-methyl-1H-pyrazoles which were subsequently diazotized and coupled with malononitrile to yield a series of pyrazolylhydrazonomalononitriles. These compounds were then reacted with hydrazine monohydrate to provide, heterocyclic dyes, which were further diazotized and coupled with 4-hexylbenzene-1,3-diol to produce novel heterocyclic tetraazo dyes which were characterized by elemental analysis and spectral methods. The antimicrobial activity and absorption characteristics of the dyes were also examined in detail.Pyrazole Solvatochromism Heterocyclic dyes Antimicrobial activity 3-Aminocrotononitrile 4-Hexylbenzene-1,3-diol

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“…Azo dyes have been intensively studied for both theoretical and practical purposes for many years [1–5]. In addition to the widespread application of azo dyes in textiles, medical areas, cosmetics, printing, drugs and food colouring, they have attracted the interest of many investigators because of their usage in high technology [6,7].…”

Section: Introductionmentioning

confidence: 99%

The synthesis, characterisation and molecular structure of a new hetarylazoindole dye studied by X‐ray diffraction, spectral analysis and density functional theory calculation

Aktan

Seferoğlu

Hökelek

et al. 2012

Coloration Technology

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1,2‐Dimethyl‐3‐(5‐methylisoxazol‐3‐yldiazenyl)‐1H‐indole was obtained by coupling 3‐amino‐5‐methylisoxazole with diazotised 1,2‐dimethylindole. It was characterised by proton and carbon nuclear magentic resonance, ultraviolet–visible, infrared and Raman spectra, and the X‐ray single crystal diffraction method. On the theoretical side, the molecular geometry, chemical shifts and the fundamental vibrational frequencies were evaluated using density functional theory. Time‐dependent density functional theory was used to evaluate the electronic excitation spectra. In addition, the scaled quantum mechanical approach was used to study the total energy distributions of the vibrational modes of the molecule. The results showed that the general agreement between experimental and calculated geometric parameters, chemical shifts and λmax values are good. Excellent agreement was found between the calculated and experimental vibrational frequencies.

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The synthesis, spectroscopic properties and theoretical calculation of some novel disperse disazo dyes derived from 3-amino-5-hydroxy-1-phenylpyrazole

Cited by 25 publications

References 51 publications

Synthesis, Characterization, Absorption and Fastness Properties of Novel Monoazo Dyes Derived from 1-Phenyl-3-amino-4-(2-thiazolilazo)pyrazol-5-one

Synthesis, Characterization, Absorption and Fastness Properties of Novel Monoazo Dyes Derived from 1-Phenyl-3-amino-4-(2-thiazolilazo)pyrazol-5-one

Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol

The synthesis, characterisation and molecular structure of a new hetarylazoindole dye studied by X‐ray diffraction, spectral analysis and density functional theory calculation

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