Journals / Gazi Üniversitesi Fen Bilimleri Dergisi Part C: Tasarım ve Teknoloji / 2023 / Cilt: 11 Sayı: 3

Structure and Spectroscopic Studies of Bis Azo Compounds with S/SO2 Bridges and Containing Cyclic-1,3-Dicarbonyl Groups

Pages
727–734
Publication Date
2023-09-27
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The results of the UV-visible and 1H-NMR spectra indicated that the compounds in chloroform, dimethylformamide (DMF), acetic acid and methanol were found in the hydrazo tautomer (keto-amine O….H-N forms) of the proposed tautomeric forms.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:A series of new bis azo dyes were synthesized starting from aromatic diamine with S/SO2 bridges and cyclic-1,3-dicarbonyl groups; contain active methylene group, namely; 3,3-dimethyl-1,5-cyclohexadione (dimedone), 1,3-cyclohexadione and 2,2-dimethyl-1,3-dioxane-4,6-dione to give 1-6.
📊
Key Findings & Data:The structure of the newly synthezed compounds was investigated by using, FT-IR, 1HNMR, LC–MS/MS and UV–Visible spectrophotometric methods, CH3OH was used in the LC-MS/MS experiments, and the molecular masses of the compounds were seen as M and M+1 protonated in the spectrum.
💡
Conclusion & Impact:The results of the UV-visible and 1H-NMR spectra indicated that the compounds in chloroform, dimethylformamide (DMF), acetic acid and methanol were found in the hydrazo tautomer (keto-amine O….H-N forms) of the proposed tautomeric forms.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Bis azo dyes · spectroscopic studies · dimedone

Abstract

A series of new bis azo dyes were synthesized starting from aromatic diamine with S/SO2 bridges and cyclic-1,3-dicarbonyl groups; contain active methylene group, namely; 3,3-dimethyl-1,5-cyclohexadione (dimedone), 1,3-cyclohexadione and 2,2-dimethyl-1,3-dioxane-4,6-dione to give 1-6. Whether the reaction is complete and the purity of the compounds were checked with TLC. The structure of the newly synthezed compounds was investigated by using, FT-IR, 1HNMR, LC–MS/MS and UV–Visible spectrophotometric methods, CH3OH was used in the LC-MS/MS experiments, and the molecular masses of the compounds were seen as M and M+1 protonated in the spectrum. In the UV-Vis spectra of these compounds, the solvent effect by using different solvents and also the acid-base effect by adding HCl or KOH to the medium were investigated. The tautomeric equilibrium forms (enol-imine O-H….N, keto-amine O….H-N forms) of the compounds were investigated according to the electronic spectrum recorded in chloroform, dimethylformamide (DMF), acetic acid, and methanol solvents. The results of the UV-visible and 1H-NMR spectra indicated that the compounds in chloroform, dimethylformamide (DMF), acetic acid and methanol were found in the hydrazo tautomer (keto-amine O….H-N forms) of the proposed tautomeric forms.

🔖

Cite This Article

ERTEN, G., ÇOLAK, N. (2023). Structure and Spectroscopic Studies of Bis Azo Compounds with S/SO2 Bridges and Containing Cyclic-1,3-Dicarbonyl Groups. Gazi Üniversitesi Fen Bilimleri Dergisi Part C: Tasarım ve Teknoloji, Cilt: 11 Sayı: 3, 727–734. https://ajindex.com/articles/962816

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (12)

  1. Albertin G, Antoniutti S, Boato M. Diazo Complexes of Osmium: Preparation of Binuclear Derivatives with Bis (Aryldiazene) and Bis (Aryldiazenido) Bridging Ligands. Inorg. Chim. Acta, 357 (2004) 1119–1133
  2. Raghu AV, Gadaginamath GS, Mathew NT, Halligudi SB, Aminabhavi TM,.Synthesis and Characterization of Novel Polyurethanes Based on 4,4-[1,4-Phenylenedidiazene-2,1-Diyl]Bis(2-Carboxyphenol) and 4,4- [1,4-Phenylenedi-Diazene-2,1-Diyl]Bis(2-Chlorophenol) Hard Segments. React. Func. Polym. 67 (2007) 503–514
  3. Shchur IV, Khudina OG, Burgart YV, Saloutin VI, Grishina MA, Potemkin VA. Synthesis, Structure, and Complexing Ability of Fluoroalkylcontaining 2,2-(Biphenyl-4,4-Diyldihydrazono)Bis(1,3-Dicarbonyl) Compounds. Russ. J. Org. Chem. 43 (2007) 1781–1787
  4. Weaver MA, Shuttleworth L. Heterocyclic diazo components. Dye Pigm. 3 (1982) 81-121
  5. Urus S, Ozdemir M, Ceyhan G, Tumer M. Chemically Modified Silica-Gel With an Azo-Schiff Ligand and Its Metal Complexes with Cu(II), Co(II), Ni(II) and Mn(II): Applications as Catalysts on the Oxidation of Cyclohexane Under Microwave Power. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 42 (2012) 382–391
  6. Kitaev YP, Buzykin BI, (1974). Gidrazony [Hydrazones], Nauka, Moscow, 416 pp. (in Russian)
  7. Kost AN, Grandberg II. Progress in Pyrazole Chemistry. Adv. Heterocycl. Chem., 6 (1966) 347-429
  8. Jeong MJ, Park JH, Lee C, Chang JY. Discotic Liquid Crystalline Hydrazone Compounds: Synthesis and Mesomorphic Properties. Org. Lett. 8 (2006) 2221–2224
  9. Chen Z, Wu Y, Gu D, Gan F. Nickel (II) and Copper (II) Complexes Containing 2-(2-(5-Substitued İsoxazol-3-Yl)Hydrazono)-5,5-Dimethylcyclohexane-1,3-Dione Ligands: Synthesis, Spectral and Thermal Characterizations. Dyes Pigm. 76 (2008) 624–631
  10. Sokolnicki J, Legendziewicz J, Amirkhanov W, Ovchinnikov V, Macalik L, Hanuza J. Comparative Optical Studies of Lanthanide Complexes with Three Types of Phosphoro-Azo Derivatives of B-Diketones. Spec. Chim. Acta A. 55 (1999) 349–367
  11. More MS, Joshi PG, Mishra YK, Khanna PK. Metal Complexes Driven from Schiff Bases fnd Semicarbazones for Biomedical and Allied Applications: A Review. Mater. Today Chem., 14 (2019) 100195–100217
  12. Torres MJ, Criado A, Ruiz M, Llanos AC, Palomares JC, Aznar J. Improved Real-Time PCR for Rapid Detection of Rifampin and Isoniazid Resistance in Mycobacterium Tuberculosis Clinical Isolates. Diag. Micr. Infects Disease., 45 (2003) 207-212