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Journal articles on the topic 'Azo hydrazone tautomerism'

Author: Grafiati

Published: 3 June 2025

Last updated: 31 July 2025

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1

Mirkovic, Jelena, Gordana Uscumlic, Aleksandar Marinkovic, and Dusan Mijin. "Azo-hydrazone tautomerism of aryl azo pyridone dyes." Chemical Industry 67, no. 1 (2013): 1–15. http://dx.doi.org/10.2298/hemind120309053m.

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In the last three or four decades disperse dyes derived from pyridones (in particular azo pyridone dyes) have gained in importance, and are widely used in various fields. These compounds have excellent coloration properties, and are suitable for the dyeing of polyester fabrics. Basic features of these dyes are simplicity of their synthesis by diazotation and azo coupling. They generally have high molar extinction coefficient with medium to high light and wet fastness. The absorption maxima of these dyes show their visible absorption wavelength ranging from yellow to orange, which can be attrib

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2

Zaharieva, Lidia, Vera Deneva, Fadhil S. Kamounah, et al. "Tautomerism and switching in 7-hydroxy-8-(azophenyl)quinoline and similar compounds." Beilstein Journal of Organic Chemistry 21 (July 10, 2025): 1404–21. https://doi.org/10.3762/bjoc.21.105.

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Tautomerism in two new azo dyes, based on 7-hydroxyquinoline, has been considered from the viewpoint of the proton crane concept. Although 8-(phenyldiazenyl)quinolin-7-ol exists in solution as a mixture of azo and two hydrazone tautomers, as shown by the experimental and theoretical results, upon irradiation switching, based on long-range proton transfer, occurs in a limited extent. 8-(4-Hydroxy-1,2,3,5-tetrafluorophenyldiazenyl)quinolin-7-ol exists as a single enol (azo) tautomer and the reduced basicity of the azo group nitrogen atoms does not allow shift of the tautomeric state neither upon

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3

Cai, Jiawei, Zhixin Li, Yanxuan Qiu, et al. "The syntheses, structures and azo–hydrazone tautomeric studies of three triazole/tetrazole azo dyes." New Journal of Chemistry 40, no. 11 (2016): 9370–79. http://dx.doi.org/10.1039/c5nj02539g.

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4

Baldini, Laura, Davide Balestri, Luciano Marchiò, and Alessandro Casnati. "A Combined Solution and Solid-State Study on the Tautomerism of an Azocalix[4]arene Chromoionophore." Molecules 28, no. 12 (2023): 4704. http://dx.doi.org/10.3390/molecules28124704.

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Azocalixarenes functionalized with cation binding sites are popular chromoionophores due to the ease of synthesis and the large complexation-induced shifts of their absorption band that originate from an azo-phenol–quinone-hydrazone tautomerism. Despite their extensive use, however, a thorough investigation of the structure of their metal complexes has not been reported. We describe herein the synthesis of a new azocalixarene ligand (2) and the study of its complexation properties with the Ca2+ cation. Through a combination of solution (1H NMR and UV-vis spectroscopies) and solid-state (X-ray

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5

Peng, Qinji, Mujie Li, Kunyu Gao, and Lubai Cheng. "Hydrazone-azo tautomerism of pyridone azo dyes: Part 1—NMR Spectra of Tautomers." Dyes and Pigments 14, no. 2 (1990): 89–99. http://dx.doi.org/10.1016/0143-7208(90)87009-r.

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6

He, Jian-Qiang, Shang-Fang Xie, Bi-Lin Lai, et al. "A new salicylaldehyde-based azo dye and its two lanthanide(iii) complexes displaying slow magnetic relaxation." Dalton Transactions 47, no. 42 (2018): 14975–84. http://dx.doi.org/10.1039/c8dt02951b.

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A new salicylaldehyde-based azo dye 5-azotriazolyl-3-methoxysalicylaldehyde (H<sub>2</sub>TMSA) displaying pH-dependent azo-hydrazone tautomerism and its two Ln<sup>3+</sup> complexes displaying slow magnetic relaxation were reported.

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7

Farghaly, Thoraya A., Magda A. Abdallah, and Mohamed R. Abdel Aziza. "Azo-Hydrazone Tautomerism and Antimicrobial activity of New substituted Imidazolines and Perimidines." JOURNAL OF ADVANCES IN CHEMISTRY 10, no. 5 (2014): 2694–704. http://dx.doi.org/10.24297/jac.v10i5.886.

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Two new series of 2-{1-[(substitutedphenyl)-hydrazono]-2-oxo-2-phenyl-ethyl}-5,5-diphenyl-3,5-dihydro-imidazol-4-one and (1H-Perimidin-2-yl)-[(substitutedphenyl)-hydrazono]-acetic acid ethyl ester were prepared by coupling the diazonium salt of aniline and its derivatives with 2-(2-oxo-2-phenyl-ethylidene)-5,5-diphenyl-imidazolidin-4-one or ethyl 3-dimethylamino-2-(1H-perimidin-2-yl)-propenoate in ethanolic sodium hydroxide solution. The structures of all the newly synthesized compounds were confirmed by spectral (IR, 1H NMR, mass) spectra , and X-ray crystallographic and elemental analyses. A

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8

Nishimura, N., K. Danjo, Y. Sueishi, and S. Yamamoto. "Solvent and Pressure Effects on the Tautomeric Equilibrium of 4-Phenylazo-1-naphthol." Australian Journal of Chemistry 41, no. 6 (1988): 863. http://dx.doi.org/10.1071/ch9880863.

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The azo-hydrazone tautomerism of 4-phenylazo-1-naphthol has been studied in ethanol-water and acetone-water systems and at high pressures. The hydrazone form is favoured by adding water to organic cosolvents and by applying pressure. The effects of solvent polarity and pressure on the equilibrium constant (KT) between the tautomers were examined by using Kirkwood-type equations applied to chemical equilibrium. Remarkable deviations were observed in the Kirkwood plots for both types of mixtures. Solvent-induced polarization, especially of the hydrazone form in a high polarity region, was sugges

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9

Özen, Alimet Sema, Pemra Doruker, and Viktorya Aviyente. "Effect of Cooperative Hydrogen Bonding in Azo−Hydrazone Tautomerism of Azo Dyes." Journal of Physical Chemistry A 111, no. 51 (2007): 13506–14. http://dx.doi.org/10.1021/jp0755645.

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10

Lyčka, Antonin. "19F-NMR study of azo-hydrazone tautomerism of some fluorine-containing azo dyes." Dyes and Pigments 12, no. 3 (1990): 179–85. http://dx.doi.org/10.1016/0143-7208(90)85010-l.

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11

Hsieh, Bing R., Denis Désilets, and Peter M. Kazmaier. "Azo-hydrazone tautomerism of an o,o'-dihydroxy azo dye-a spectroscopic study." Dyes and Pigments 14, no. 3 (1990): 165–89. http://dx.doi.org/10.1016/0143-7208(90)87015-u.

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12

Lyčka, Antonín, Josef Jirman, Bohdan Schneider, and Jaroslav Straka. "15N CP-MAS NMR study of azo-hydrazone tautomerism of some Azo dyes." Magnetic Resonance in Chemistry 26, no. 6 (1988): 507–10. http://dx.doi.org/10.1002/mrc.1260260614.

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13

Loghmani-Khouzani, H., H. Mehrabi, M. M. M. Sadeghi та R. Gawinecki. "Study of hydrazone-Hydrazoimine tautomerism in α-Azo-6-ketomethylphenanthridines". Journal of the Iranian Chemical Society 6, № 1 (2009): 129–37. http://dx.doi.org/10.1007/bf03246511.

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14

Lyčka, Antonin, and Valdimir Macháček. "13C and 15N-NMR studies of the azo-hydrazone tautomerism of some azo dyes." Dyes and Pigments 7, no. 3 (1986): 171–85. http://dx.doi.org/10.1016/0143-7208(86)85008-2.

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15

Lee, Ho Yong, Xinli Song, Hyunsoo Park, Mu-Hyun Baik, and Dongwhan Lee. "Torsionally ResponsiveC3-Symmetric Azo Dyes: Azo−Hydrazone Tautomerism, Conformational Switching, and Application for Chemical Sensing." Journal of the American Chemical Society 132, no. 34 (2010): 12133–44. http://dx.doi.org/10.1021/ja105121z.

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16

Cheon, Kap-Soo, Yong S. Park, Peter M. Kazmaier, and Erwin Buncel. "Studies of azo–hydrazone tautomerism and H-bonding in azo-functionalized dendrimers and model compounds." Dyes and Pigments 53, no. 1 (2002): 3–14. http://dx.doi.org/10.1016/s0143-7208(01)00096-1.

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17

Fedorov, L. A., and S. A. Sokolovskii. "13C NMR spectra and azoquinone hydrazone tautomerism of azo-2-naphthols and azo-1-naphthols." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 37, no. 10 (1988): 2043–48. http://dx.doi.org/10.1007/bf00953401.

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18

Peng, Q. "Hydrazone-azo tautomerism of pyridone azo dyes Part II: Relationship between structure and pH values." Dyes and Pigments 15, no. 4 (1991): 263–74. http://dx.doi.org/10.1016/0143-7208(91)80011-w.

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19

Yamamoto, Kiyoshi, Kiyoshi Nakai, and Toshio Kawaguchi. "15N NMR study of azo-hydrazone tautomerism of some water-soluble dyes." Dyes and Pigments 11, no. 3 (1989): 173–77. http://dx.doi.org/10.1016/0143-7208(89)80002-6.

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20

VICTORY, P., A. ALVAREZ-LARENA, X. BATLLORI, et al. "ChemInform Abstract: 2,3,6-Trioxypentafulvenes. Part 4. Azo-Hydrazone Tautomerism of 2,3,6- Trioxypentafulvenes." ChemInform 25, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199417108.

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21

Matazo, Deborah R. C., Rômulo A. Ando, Antonio C. Borin, and Paulo S. Santos. "Azo−Hydrazone Tautomerism in Protonated Aminoazobenzenes: Resonance Raman Spectroscopy and Quantum-Chemical Calculations." Journal of Physical Chemistry A 112, no. 19 (2008): 4437–43. http://dx.doi.org/10.1021/jp800217c.

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22

Satheshkumar, A., E. H. El-Mossalamy, R. Manivannan, et al. "Anion induced azo-hydrazone tautomerism for the selective colorimetric sensing of fluoride ion." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 128 (July 2014): 798–805. http://dx.doi.org/10.1016/j.saa.2014.02.200.

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23

Szántay, Jr, Csaba, Zsuzsanna Csepregi, Péter Aranyosi, István Rusznák, László Tőke, and András Víg. "Nuclear Magnetic Resonance Investigations of the Azo-Hydrazone Tautomerism of Azoreactive Dye Chromophores." Magnetic Resonance in Chemistry 35, no. 5 (1997): 306–10. http://dx.doi.org/10.1002/(sici)1097-458x(199705)35:5<306::aid-omr93>3.0.co;2-n.

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24

Choudhari, Amol S., Sharad R. Patil, and Nagaiyan Sekar. "Solvatochromism, halochromism, and azo-hydrazone tautomerism in novel V-shaped azo-azine colorants - consolidated experimental and computational approach." Coloration Technology 132, no. 5 (2016): 387–98. http://dx.doi.org/10.1111/cote.12226.

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25

Y., M. ISSA, F. EL-HAWARY W., E. MOUSTAFA M., and REFAAT M. "Spectroscopic Studies on some New Azo Dyes derived from 4-Methylesculetin and their Biological Activity." Journal of Indian Chemical Society Vol. 74, Oct 1997 (1997): 777–80. https://doi.org/10.5281/zenodo.5896844.

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Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt Chemistry Department, Faculty of Science, Benha University, Egypt <em>Manuscript received 18 June 1996, accepted 4 December 1996</em> Some new mono azo dyes derived from 6,7-dihydroxy-4-methylcoumarin have been prepared and their electronic absorption spectra have been investigated in organic solvents of varying polarities. The spectra, in ethanol, display mainly five absorption bands which are assigned to their appropriate electronic transitions. The effect of substituents on the absorption spectra have been investigated.

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26

Zhao, Xiao-Lei, Min Wang, Jiao Geng, and Wei Huang. "Fenton-like reactions for pyrazolone ester based heterocyclic dyes with reversible hydrazone-azo tautomerism." Polyhedron 202 (July 2021): 115208. http://dx.doi.org/10.1016/j.poly.2021.115208.

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27

Chen, Jinhuan, and Zhenming Yin. "Cooperative intramolecular hydrogen bonding induced azo-hydrazone tautomerism of azopyrrole: Crystallographic and spectroscopic studies." Dyes and Pigments 102 (March 2014): 94–99. http://dx.doi.org/10.1016/j.dyepig.2013.10.036.

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28

Peng, Q. "Hydrazone-azo tautomerism of pyridone azo dyes Part III—effect of dye structure and solvents on the dissociation of pyridone azo dyes." Dyes and Pigments 18, no. 4 (1992): 271–86. http://dx.doi.org/10.1016/0143-7208(92)80017-h.

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29

Shawali, Ahmad S., Said Elsheikh, and Cyril Párkányi. "Cyclization of thiohydrazonate esters and azo-hydrazone tautomerism of 2-arylhydrazono-3-oxo-1,4-benzothiazines." Journal of Heterocyclic Chemistry 40, no. 2 (2003): 207–12. http://dx.doi.org/10.1002/jhet.5570400202.

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30

Hihara, T. "An analysis of azo-hydrazone tautomerism of reactive azobenzene and pyrazolinyl-azo dyes using the semiempirical molecular orbital PM5 method." Dyes and Pigments 61, no. 3 (2004): 199–225. http://dx.doi.org/10.1016/j.dyepig.2003.10.010.

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31

Pavlović, Gordana, Livio Racané, Helena Čičak, and Vesna Tralić-Kulenović. "The synthesis and structural study of two benzothiazolyl azo dyes: X-ray crystallographic and computational study of azo–hydrazone tautomerism." Dyes and Pigments 83, no. 3 (2009): 354–62. http://dx.doi.org/10.1016/j.dyepig.2009.06.002.

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32

Hihara, T. "Azo-hydrazone tautomerism of phenylazonaphthol sulfonates and their analysis using the semiempirical molecular orbital PM5 method." Dyes and Pigments 59, no. 1 (2003): 25–41. http://dx.doi.org/10.1016/s0143-7208(03)00093-7.

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33

Zheng, Dong, Yuming Gu, Xiang Li, Lizhu Zhang, Wei Zhao, and Jing Ma. "Hydrogen Bonding Promoted Tautomerism between Azo and Hydrazone Forms in Calcon with Multistimuli Responsiveness and Biocompatibility." Journal of Chemical Information and Modeling 59, no. 5 (2019): 2110–22. http://dx.doi.org/10.1021/acs.jcim.8b00985.

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34

Kawashima, Norimichi, Naoki Fujimoto, and Kenjiro Meguro. "Determination of critical micelle concentration of several nonionic surfactants by azo-hydrazone tautomerism of anionic dye." Journal of Colloid and Interface Science 103, no. 2 (1985): 459–65. http://dx.doi.org/10.1016/0021-9797(85)90122-5.

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35

Habibi, Mohammad Hossein, Ali Hassanzadeh, and Asghar Zeini-Isfahani. "Effect of dye aggregation and azo–hydrazone tautomerism on the photocatalytic degradation of Solophenyl red 3BL azo dye using aqueous TiO2 suspension." Dyes and Pigments 69, no. 3 (2006): 111–17. http://dx.doi.org/10.1016/j.dyepig.2005.02.016.

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36

Tadić, Julijana D., Jelena M. Lađarević, Željko J. Vitnik, et al. "Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity." Dyes and Pigm 187, March (2021): 109123. https://doi.org/10.1016/j.dyepig.2020.109123.

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Seven novel azo dyes with 2-pyridone and dihydropyrimidinone moieties have been synthesized and thoroughly characterized. The azo-hydrazone tautomerism has been investigated by experimental and theoretical approaches. The optimizations of geometries have been performed with density functional theory (DFT). The vibrational and NMR spectra were calculated and correlated with experimental ones. Furthermore, quantum chemical descriptors were calculated and MEP maps were plotted to determine biological reactivity of dyes. The antioxidant assay evinced that 5, 6 and 7 are promising antioxidant

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37

Maldonado, Tamara, Erick Flores, Leonel Llanos, et al. "Azo–hydrazone tautomerism in organometallic complexes triggered by a -Re(CO)3(L) core: A spectroscopic and theoretical study." Dyes and Pigments 197 (January 2022): 109953. http://dx.doi.org/10.1016/j.dyepig.2021.109953.

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38

Umape, Prashant G., Vikas S. Patil, Vikas S. Padalkar, et al. "Synthesis and characterization of novel yellow azo dyes from 2-morpholin-4-yl-1,3-thiazol-4(5H)-one and study of their azo–hydrazone tautomerism." Dyes and Pigments 99, no. 2 (2013): 291–98. http://dx.doi.org/10.1016/j.dyepig.2013.05.002.

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39

Lyčka, Antonı́n, Zdeněk Vrba, and Martin Vrba. "15N, 13C and 1H NMR spectra and azo-hydrazone tautomerism of some phenylazo compounds derived from 1,3- and 1,5-dihydroxynaphthalene." Dyes and Pigments 47, no. 1-2 (2000): 45–51. http://dx.doi.org/10.1016/s0143-7208(00)00062-0.

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40

Lyčka, Antonı́n. "15N, 13C and 1H NMR spectra and azo-hydrazone tautomerism of some dyes prepared by coupling of 1-naphthalenediazonium salt." Dyes and Pigments 43, no. 1 (1999): 27–32. http://dx.doi.org/10.1016/s0143-7208(99)00032-7.

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41

Hu, Bin, Gang Wang, Wei You, Wei Huang, and Xiao-Zeng You. "Azo-hydrazone tautomerism by in situ CuII ion catalysis and complexation with the H2O2 oxidant of C.I. Disperse Yellow 79." Dyes and Pigments 91, no. 2 (2011): 105–11. http://dx.doi.org/10.1016/j.dyepig.2011.03.017.

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42

Dostanić, J., D. Mijin, G. Ušćumlić, D. M. Jovanović, M. Zlatar, and D. Lončarević. "Spectroscopic and quantum chemical investigations of substituent effects on the azo-hydrazone tautomerism and acid–base properties of arylazo pyridone dyes." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 123 (April 2014): 37–45. http://dx.doi.org/10.1016/j.saa.2013.12.064.

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43

Chen, Xiao-Chun, Tao Tao, Yin-Ge Wang, Yu-Xin Peng, Wei Huang, and Hui-Fen Qian. "Azo-hydrazone tautomerism observed from UV-vis spectra by pH control and metal-ion complexation for two heterocyclic disperse yellow dyes." Dalton Transactions 41, no. 36 (2012): 11107. http://dx.doi.org/10.1039/c2dt31102j.

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44

Vannucci, Giulia, Maria Vega Cañamares, Silvia Prati, and Santiago Sanchez‐Cortes. "Study of the azo‐hydrazone tautomerism of Acid Orange 20 by spectroscopic techniques: UV–Visible, Raman, and surface‐enhanced Raman scattering." Journal of Raman Spectroscopy 51, no. 8 (2020): 1295–304. http://dx.doi.org/10.1002/jrs.5906.

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45

Hihara, Toshio, Yasuyo Okada, and Zenzo Morita. "Reactivity of phenylazonaphthol sulfonates, their estimation by semiempirical molecular orbital PM5 method, and the relation between their reactivity and azo-hydrazone tautomerism." Dyes and Pigments 59, no. 3 (2003): 201–22. http://dx.doi.org/10.1016/s0143-7208(03)00109-8.

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46

Shawali, Ahmad S., Sharifia S. Alkaabi, and Magda A. Abdallah. "A study of azo-hydrazone tautomerism in 3-phenyl-4-arylazo-5-isozaolones by1H-NMR spectra of15N-labeled compounds and HMO method." Archives of Pharmacal Research 14, no. 3 (1991): 237–41. http://dx.doi.org/10.1007/bf02876862.

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47

Ly?ka, Anton�n, and Heinz Mustroph. "15N- and13C-N.M.R. Study of Azo-hydrazone Tautomerism of 3-methyl-1-phenylpyrazole-4,5-dione 4-phenylhydrazone in dimethyl sulphoxide and pyridine." Journal f�r Praktische Chemie 331, no. 1 (1989): 11–14. http://dx.doi.org/10.1002/prac.19893310103.

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48

Khristenko, Inna, and Volodymyr Ivanov. "Absorption spectra of Nitrazine Yellow indicator. Experimental data and quantum chemical evaluations." Kharkov University Bulletin Chemical Series, no. 42 (June 21, 2024): 68–76. https://doi.org/10.26565/2220-637x-2024-42-08.

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This article presents an experimental investigation and theoretical analysis of the electronic absorption spectra of the indicator nitrazine yellow (NY) in aqueous solutions. Quantum chemical modeling of electronically excited states is performed within the framework of time-dependent density functional theory (TD-DFT). A variety of approaches and basis sets are explored, particularly focusing on the B3LYP and CAM-B3LYP functionals. The standard 6-31+G(d,p) basis set is employed, along with combinations using pseudopotential basis sets for Na and S atoms. In the first variant of calculations,

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49

Farghaly, Thoraya A., and Zeinab A. Abdallah. "Synthesis, azo-hydrazone tautomerism and antitumor screening of N-(3-ethoxycarbonyl-4,5,6,7-tetrahydro-benzo[b]thien-2-yl)-2-arylhydrazono-3-oxobutanamide derivatives." Arkivoc 2008, no. 17 (2009): 295–305. http://dx.doi.org/10.3998/ark.5550190.0009.h28.

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50

Hassanzadeh, A., A. Zeini-Isfahani, M. H. Habibi, M. R. A. Poor Heravi, and M. Abdollahi-Alibeik. "1H, 13C, NH, HH, CH COSY, HH NOESY NMR and UV–vis studies of Solophenyl red 3BL dye azo-hydrazone tautomerism in various solvents." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 63, no. 2 (2006): 247–54. http://dx.doi.org/10.1016/j.saa.2005.03.035.

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