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

Yıl 2023, Cilt: 11 Sayı: 3, 727 - 734, 27.09.2023
https://doi.org/10.29109/gujsc.1285026

Öz

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.

Destekleyen Kurum

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Proje Numarası

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Teşekkür

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Kaynakça

  • [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.
  • [13] Tian NZ, Zhou Y, Sun SG, Ding Y, Zhong LW. Synthesis of Tetrahexahedral Platinum Nanocrystals with High-İndex Facets and High Electro-Oxidation Activity. Sci. Mag., 316 (2007) 732-735.
  • [14] Raja A, Rajendiran V, Mahesweri PU, Balamuugan R, Kilner CA, Halcrow MA. Copper (II) Complexes of Tridentate Pyridylmethylethylenediamines: Role of Ligand Steric Hindrance on DNA Binding and Cleavage. J. Inorg. Biochem., 99 (2005) 1717-1732.
  • [15] Abdel-Rahman LH, Abu-Dief AM, Ismail M, Ismael NM. Synthesis, Characterization, And Biological Activity of New Mixed Ligand Transition Metal Complexes of Glutamine, Glutaric, and Glutamic Acid with Nitrogen Based Ligands. Inorg. Nano-Metal Chem., 47 (2017) 467-480.
  • [16] Maria CSL, Marcelle LF, Marcus VNS, Monica AP, Thatyana RAV, Maria G, Henriques MO. Synthesis and Anti-Mycobacterial Activity of (E)-N′-(mono substituted-benzylidene)isonicotino hydrazide Derivatives Eur. J. Med. Chem., 43 (2008) 1344-1347.
  • [17] Samir AC, Edson FS, Marcus VN, Maria CSL, Felipe RV. Synthesis and Antimycobacterial Evaluation of New Trans-Cinnamic Acid Hydrazide Derivatives. Bio. Org Med. Chem Lett., 18 (2008) 538-541.
  • [18] Manjunatha B, Bodke YD, Nagaraja O, Nagaraju G, Sridhar MA. Coumarin-Benzothiazole Based Azo Dyes: Synthesis, Characterization, Computational, Photophysical and Biological Studies. J. Mol. Struct. 1246 (2021) 131170–131185.
  • [19] Weldegebrieal GK. Synthesis Method, Antibacterial and Photocatalytic Activity of Zno Nanoparticles for Azo Dyes in Wastewater Treatment: A Review. Inorg. Chem. Commun. 120 (2020) 108140–108211.
  • [20] Gaffer HE. Antimicriobial Sulphonamide Azo Dyes, Color. Technol., 135 (2019) 484–500.
  • [21] Kornıs G, Katritzky AR. (ed. 1984) l,3,4-Thiadiazoles in Comprehensive Heterocyclic Chemistry, Pergamon Press, Vol. 6, Part 4B, 545-578.
  • [22] Allard N, Beaupre S, Aich BR, Najari A, Tao Y, Leclerc M. Synthesis and characterization of new poly (thieno[3,4-d]thiazole) derivatives for photovoltaic applications. Macromolecules, 44 (2011) 7184–7187.
  • [23] Zonouzi A, Rezaei MH, Mirzazadeh R, Arjomand MR. Solvent-free Synthesis of Halogenated Furo[2,3-d] pyrimidines and Their Cytotoxic Activity on the T47D Breast Cancer Cell Line. Organic Preparations and Procedures International. 52 (2020) 374-380.
  • [24] Zaky RR, Yousef TA. Spectral, Magnetic, Thermal, Molecular Modelling, ESR Studies and Antimicrobial Activity of (E)-3-(2-(2-Hydroxybenzylidene) Hydrazinyl)-3-Oxo-N(Thiazole-2-Yl)Propanamide Complexes. J. Mol. Struct. 1002 (2011) 76-85.
  • [25] Santini C, Pellei M, Gandin V, Porchia M, Tisato F, Marzano C. Advances in Copper Complexes as Anticancer Agents Chem. Rev., 114 (2014) 815-862.
  • [26] Lu Y, Li CM, Wang Z, Ross CR, Chen J, Dalton JT, Li W, Miller DD. Discovery of 4-Substituted Methoxybenzoyl-Aryl-Thiazole as Novel Anticancer Agents: Synthesis, Biological Evaluation, and Structure-Activity Relationships. J. Med. Chem., 52 (2009) 1701-1711.
  • [27] Lombardo LJ, Lee FY, Chen P, Norris D, Barrish JC, Behnia K, Castaneda S, Cornelius LAM, Das J, Doweyko AM, Fairchild C, Hunt JT, Inigo I, Johnston K, Kamath A, Kan D, Klei H, Marathe P, Pang S, Peterson R, Pitt S, Schieven GL, Schmidt RJ, Tokarski J, Wen M-L, Wityak J, Borzilleri RM. Discovery of N-(2-Chloro-6-methyl- phenyl)-2-(6-(4-(2-hydroxyethyl)- piperazin-1-yl)-2-methylpyrimidin-4- ylamino)thiazole-5-carboxamide (BMS-354825), a Dual Src/Abl Kinase Inhibitor with Potent Antitumor Activity in Preclinical Assays. J. Med. Chem., 47 (2004) 6658-6661.
  • [28] Khan E, Gul Z, Shahzad A, Jan SM, Ullah F, Tahir MN. Coordination Compounds of 4,5,6,7-Tetrahydro-1H-İndazole with Cu(II), Co(II) and Ag(I): Structural, Antimicrobial, Antioxidant and Enzyme Inhibition Studies, J. Coord. Chem., 70 (2017) 4054-4069.
  • [29] Nagasundaram N, Govindhan C, Sumitha S, Sedhu N, Raguvaran K, Santhosh S, Lalitha A. Synthesis, Characterization and Biological Evaluation of Novel Azo Fused 2,3-Dihydro-1H-Perimidine Derivatives: In Vitro Antibacterial, Antibiofilm, Anti-Quorum Sensing, DFT, in Silico ADME and Molecular Docking Studies J. Mol. Struct. , 248 (2022) 131437–131449.
  • [30] Gregory P. (2002). Industrial Dyes: chemistry, Properties and Applications, Wiley- VCH, Weinheim, 543-585.
  • [31] Bamfield P, Hutchings MG. (2010). Chromic Phenomena: Technological Applications of Colour Chemistry, 2nd ed., RSC, Cambridge.
  • [32] Zollinger H. (2003). Color Chemistry: Synthesis, Properties and Applications of Organic Dyes and Pigments, 3rd ed., Wiley-VCH, Weinheim.
  • [33] Çatıkkas B, Aktan E, Yalçın E. Vibrational and electronic investigations, NLO, FMO analysis on a hetarylazoindole disperse dye by density functional theory. J. Mol. Struct., 1117 (2016) 218–226.
  • [34] Aysha T, El-Sedik, M, Megied SAE, Ibrahim H, Youssef Hrdina YR. Synthesis, Spectral Study and Application of Solid State Fluorescent Reactive Disperse Dyes and Their Antibacterial Activity, Arab. J. Chem., 12 (2019) 225–235.
  • [35] Dopanay K, Keleştemur U, Balcıoğlu S, Ateş B, Altundaş A. Synthesis, Reaction, and Evaluation of The Anticancer Activity of 6,7,8,9,-Tetrahydro-5h-Cyclohepta [4,5] Selenopheno [2,3-D] Pyrimidine Derivatives. Tur J. Chem., 40 (2016) 631-640.
  • [36] Drew MGB. Phenylhydrazone Derivatives of Dimedone: Hydrogen Bonding, Spectral (I3C and H Nuclear Magnetic Resonance) and Conformational Considerations. Crystal and Molecular Structures Of 5,5-Dimethylcyclohexane-1, 2,3-Trione 2-(4-Methylphenylhydrazone) (1) and 5, 5-Dimethylcyclohexane-1,2,3-Trione 2-(4-Nitrophenylhydrazone) (2), J Chem Soc. Perkin Trans II, (1982) 1297–1303.
  • [37] Mohareb RM, Al Farouk FO, Wardakhan WW. Uses of Dimedone for the Synthesis of New Heterocyclic Derivatives with Anti-Tumor, C-Met, Tyrosine, and Pim-1 Kinases İnhibitions. Medicinal Chemistry Research, 27 (2018) 1984-2003.
  • [38] Silverstein RM, Bassler GC. Spectrometric identification of organic compounds. J Chem Educ. 39 (1962) 546.
  • [39] Karcı F, Karcı F., Synthesis and Tautomeric Structures of Some Novel Thiophene-Based Bis-Heterocyclic Monoazo Dyes, J Mol Struct., 1024 (2012) 117–122.
  • [40] Çiçen G, Karabacak Atay Ç, Tilki T. Disazo Dyes Containing Pyrazole and Benzothiazole Moieties: Synthesis, Characterization, Absorption Characteristics and Tautomeric Structures, Res Chem Intermed., 43 (2017), 6803-6816.
  • [41] Omar AZ, El-Rahman MA, El-Sadany SK, Hamed EA, El-Atawy MA. Synthesis of Novel Bisazo Disperse Dyes: Spectroscopic Characterization, DFT Study and Dyeing of Polyester, Dyes Pigm., 196 (2021), 109831.
Yıl 2023, Cilt: 11 Sayı: 3, 727 - 734, 27.09.2023
https://doi.org/10.29109/gujsc.1285026

Öz

Proje Numarası

-

Kaynakça

  • [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.
  • [13] Tian NZ, Zhou Y, Sun SG, Ding Y, Zhong LW. Synthesis of Tetrahexahedral Platinum Nanocrystals with High-İndex Facets and High Electro-Oxidation Activity. Sci. Mag., 316 (2007) 732-735.
  • [14] Raja A, Rajendiran V, Mahesweri PU, Balamuugan R, Kilner CA, Halcrow MA. Copper (II) Complexes of Tridentate Pyridylmethylethylenediamines: Role of Ligand Steric Hindrance on DNA Binding and Cleavage. J. Inorg. Biochem., 99 (2005) 1717-1732.
  • [15] Abdel-Rahman LH, Abu-Dief AM, Ismail M, Ismael NM. Synthesis, Characterization, And Biological Activity of New Mixed Ligand Transition Metal Complexes of Glutamine, Glutaric, and Glutamic Acid with Nitrogen Based Ligands. Inorg. Nano-Metal Chem., 47 (2017) 467-480.
  • [16] Maria CSL, Marcelle LF, Marcus VNS, Monica AP, Thatyana RAV, Maria G, Henriques MO. Synthesis and Anti-Mycobacterial Activity of (E)-N′-(mono substituted-benzylidene)isonicotino hydrazide Derivatives Eur. J. Med. Chem., 43 (2008) 1344-1347.
  • [17] Samir AC, Edson FS, Marcus VN, Maria CSL, Felipe RV. Synthesis and Antimycobacterial Evaluation of New Trans-Cinnamic Acid Hydrazide Derivatives. Bio. Org Med. Chem Lett., 18 (2008) 538-541.
  • [18] Manjunatha B, Bodke YD, Nagaraja O, Nagaraju G, Sridhar MA. Coumarin-Benzothiazole Based Azo Dyes: Synthesis, Characterization, Computational, Photophysical and Biological Studies. J. Mol. Struct. 1246 (2021) 131170–131185.
  • [19] Weldegebrieal GK. Synthesis Method, Antibacterial and Photocatalytic Activity of Zno Nanoparticles for Azo Dyes in Wastewater Treatment: A Review. Inorg. Chem. Commun. 120 (2020) 108140–108211.
  • [20] Gaffer HE. Antimicriobial Sulphonamide Azo Dyes, Color. Technol., 135 (2019) 484–500.
  • [21] Kornıs G, Katritzky AR. (ed. 1984) l,3,4-Thiadiazoles in Comprehensive Heterocyclic Chemistry, Pergamon Press, Vol. 6, Part 4B, 545-578.
  • [22] Allard N, Beaupre S, Aich BR, Najari A, Tao Y, Leclerc M. Synthesis and characterization of new poly (thieno[3,4-d]thiazole) derivatives for photovoltaic applications. Macromolecules, 44 (2011) 7184–7187.
  • [23] Zonouzi A, Rezaei MH, Mirzazadeh R, Arjomand MR. Solvent-free Synthesis of Halogenated Furo[2,3-d] pyrimidines and Their Cytotoxic Activity on the T47D Breast Cancer Cell Line. Organic Preparations and Procedures International. 52 (2020) 374-380.
  • [24] Zaky RR, Yousef TA. Spectral, Magnetic, Thermal, Molecular Modelling, ESR Studies and Antimicrobial Activity of (E)-3-(2-(2-Hydroxybenzylidene) Hydrazinyl)-3-Oxo-N(Thiazole-2-Yl)Propanamide Complexes. J. Mol. Struct. 1002 (2011) 76-85.
  • [25] Santini C, Pellei M, Gandin V, Porchia M, Tisato F, Marzano C. Advances in Copper Complexes as Anticancer Agents Chem. Rev., 114 (2014) 815-862.
  • [26] Lu Y, Li CM, Wang Z, Ross CR, Chen J, Dalton JT, Li W, Miller DD. Discovery of 4-Substituted Methoxybenzoyl-Aryl-Thiazole as Novel Anticancer Agents: Synthesis, Biological Evaluation, and Structure-Activity Relationships. J. Med. Chem., 52 (2009) 1701-1711.
  • [27] Lombardo LJ, Lee FY, Chen P, Norris D, Barrish JC, Behnia K, Castaneda S, Cornelius LAM, Das J, Doweyko AM, Fairchild C, Hunt JT, Inigo I, Johnston K, Kamath A, Kan D, Klei H, Marathe P, Pang S, Peterson R, Pitt S, Schieven GL, Schmidt RJ, Tokarski J, Wen M-L, Wityak J, Borzilleri RM. Discovery of N-(2-Chloro-6-methyl- phenyl)-2-(6-(4-(2-hydroxyethyl)- piperazin-1-yl)-2-methylpyrimidin-4- ylamino)thiazole-5-carboxamide (BMS-354825), a Dual Src/Abl Kinase Inhibitor with Potent Antitumor Activity in Preclinical Assays. J. Med. Chem., 47 (2004) 6658-6661.
  • [28] Khan E, Gul Z, Shahzad A, Jan SM, Ullah F, Tahir MN. Coordination Compounds of 4,5,6,7-Tetrahydro-1H-İndazole with Cu(II), Co(II) and Ag(I): Structural, Antimicrobial, Antioxidant and Enzyme Inhibition Studies, J. Coord. Chem., 70 (2017) 4054-4069.
  • [29] Nagasundaram N, Govindhan C, Sumitha S, Sedhu N, Raguvaran K, Santhosh S, Lalitha A. Synthesis, Characterization and Biological Evaluation of Novel Azo Fused 2,3-Dihydro-1H-Perimidine Derivatives: In Vitro Antibacterial, Antibiofilm, Anti-Quorum Sensing, DFT, in Silico ADME and Molecular Docking Studies J. Mol. Struct. , 248 (2022) 131437–131449.
  • [30] Gregory P. (2002). Industrial Dyes: chemistry, Properties and Applications, Wiley- VCH, Weinheim, 543-585.
  • [31] Bamfield P, Hutchings MG. (2010). Chromic Phenomena: Technological Applications of Colour Chemistry, 2nd ed., RSC, Cambridge.
  • [32] Zollinger H. (2003). Color Chemistry: Synthesis, Properties and Applications of Organic Dyes and Pigments, 3rd ed., Wiley-VCH, Weinheim.
  • [33] Çatıkkas B, Aktan E, Yalçın E. Vibrational and electronic investigations, NLO, FMO analysis on a hetarylazoindole disperse dye by density functional theory. J. Mol. Struct., 1117 (2016) 218–226.
  • [34] Aysha T, El-Sedik, M, Megied SAE, Ibrahim H, Youssef Hrdina YR. Synthesis, Spectral Study and Application of Solid State Fluorescent Reactive Disperse Dyes and Their Antibacterial Activity, Arab. J. Chem., 12 (2019) 225–235.
  • [35] Dopanay K, Keleştemur U, Balcıoğlu S, Ateş B, Altundaş A. Synthesis, Reaction, and Evaluation of The Anticancer Activity of 6,7,8,9,-Tetrahydro-5h-Cyclohepta [4,5] Selenopheno [2,3-D] Pyrimidine Derivatives. Tur J. Chem., 40 (2016) 631-640.
  • [36] Drew MGB. Phenylhydrazone Derivatives of Dimedone: Hydrogen Bonding, Spectral (I3C and H Nuclear Magnetic Resonance) and Conformational Considerations. Crystal and Molecular Structures Of 5,5-Dimethylcyclohexane-1, 2,3-Trione 2-(4-Methylphenylhydrazone) (1) and 5, 5-Dimethylcyclohexane-1,2,3-Trione 2-(4-Nitrophenylhydrazone) (2), J Chem Soc. Perkin Trans II, (1982) 1297–1303.
  • [37] Mohareb RM, Al Farouk FO, Wardakhan WW. Uses of Dimedone for the Synthesis of New Heterocyclic Derivatives with Anti-Tumor, C-Met, Tyrosine, and Pim-1 Kinases İnhibitions. Medicinal Chemistry Research, 27 (2018) 1984-2003.
  • [38] Silverstein RM, Bassler GC. Spectrometric identification of organic compounds. J Chem Educ. 39 (1962) 546.
  • [39] Karcı F, Karcı F., Synthesis and Tautomeric Structures of Some Novel Thiophene-Based Bis-Heterocyclic Monoazo Dyes, J Mol Struct., 1024 (2012) 117–122.
  • [40] Çiçen G, Karabacak Atay Ç, Tilki T. Disazo Dyes Containing Pyrazole and Benzothiazole Moieties: Synthesis, Characterization, Absorption Characteristics and Tautomeric Structures, Res Chem Intermed., 43 (2017), 6803-6816.
  • [41] Omar AZ, El-Rahman MA, El-Sadany SK, Hamed EA, El-Atawy MA. Synthesis of Novel Bisazo Disperse Dyes: Spectroscopic Characterization, DFT Study and Dyeing of Polyester, Dyes Pigm., 196 (2021), 109831.
Toplam 41 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Tasarım ve Teknoloji
Yazarlar

Gülnihal Erten 0000-0002-5441-2292

Naki Çolak 0000-0001-7181-9556

Proje Numarası -
Erken Görünüm Tarihi 19 Ağustos 2023
Yayımlanma Tarihi 27 Eylül 2023
Gönderilme Tarihi 18 Nisan 2023
Yayımlandığı Sayı Yıl 2023 Cilt: 11 Sayı: 3

Kaynak Göster

APA 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 University Journal of Science Part C: Design and Technology, 11(3), 727-734. https://doi.org/10.29109/gujsc.1285026

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