Synthesis, Characterization and Determination Antioxidant Activities for New Azo Dyederived from Sulfamethoxazole and Some Metal Ion Complexes

Authors

Amnah Mahdi Abdullah Department of Chemistry, College of Science for Women University of Baghdad, Baghdad, Iraq https://orcid.org/0000-0002-9187-2677
Abbas Ali Salih Al-Hamdani Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad, Iraq. https://orcid.org/0000-0002-2506-986X
Wail Al Zoubi School of Materials Science and Engineering,Yeungnam University, Gyeongsan 712-749, South Koria https://orcid.org/0000-0002-9959-1431

DOI:

https://doi.org/10.30526/37.2.3279

Keywords:

Antioxidant , Mass spectroscopy , Azo dye, 1-(2,4,6-Trihydroxy-phenyl)-ethanone , Thermal analysis.

Abstract

Diazotization reaction between 1-(2,4,6-trihydroxy-phenyl)-ethanone and diazonium salts produced the ligand 4-(3-Acetyl-2,4,6-trihydroxy-phenylazo)-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide, which in turn reacted with the metal ions (Ni²⁺, Zn²⁺, Pd²⁺ and Pt⁴⁺) forming stable complexes with Octahedral geometry suggest of (Ni²⁺ and Pt⁴⁺), Zn²⁺ complex Tetrahedral and Pd²⁺ complex Square planer. The creation of such complexes was detected by employing spectroscopic means involving ultraviolet-visible, which proved the obtained geometries; FT-IR confirmed the formation of the azo group and the coordination with metal ions through it. Thermogravimetric analysis studies demonstrated the coordination of water residues (aqua or hydrate) with metal ions inside the coordination sphere, as well as used curve DSC to calculate the thermodynamic parameters ΔH, ΔS, and ΔG. Moreover, element microanalysis and atomic absorption gave corresponding outcomes with theoretically counting outcomes. Neuclearmagnatic resonances for ¹H and ¹³C, chlorine atoms, and magnetic moment quantifications also indicate the formation of azo dye ligand. The ligand and new complexes showed antioxidant abilities to scavenge free radicals.

References

Al-Hamdani, A.A.S.; Balkhi, A.M., Shaker, A.F.S.A. Synthesis and investigation of thermal properties of vanadyl complexes with azo-containing Schiff-base dyes. Journal of Saudi Chemical Society 2016, 20(5), 487-501. https://doi.org/10.1016/j.jscs.2012.08.001.

Resheed, F.A.; AL-Hamdani, A.A.S.; Abdullah, S.M. Green synthesis zinc nanoparticles in the treatment of heavy metals in the form of complexes. Ibn Al-Haitham Journal For Pure and Applied Sciences 2023, 36(3),201-213. https://doi.org/10.30526/36.3.3056.

Malik, H.; Akhter, Z.; Shahbaz, M.; Yousuf, S.; Munawar, K.S.; Muhammad, S.; Ahmad, T. Synthesis, spectroscopic characterization, single crystal, theoretical investigation, and biological screenings of azo-based moieties. Journal of Molecular Structure 2022, 1270, 133867.

https://doi. 10.1016/j.molstruc.2022.13386.

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. Journal of Molecular Structure 2022, 124,131437.

‏ https://doi.org/10.1016/j.molstruc.2021.131437.

Al-Daffay, R.K.H.; Al-Hamdani, AAS. Synthesis and characterization of some metals complexes with Nnew acidicazo ligand 4-[(2-Amino-4-Phenylazo)-Methyl]-cyclohexane carboxylic acid. Iraqi Journal of Science 2022,63(8),3264-3275. https://doi.org/10.24996/ijs.2022.63.8.2.

Reda, SM.; Al-Hamdani AAS. Synthesis, characterization, thermal analysis and bioactivity of some transition metals complexes with new azo ligand. Chemical Methodologies 2022, 6(6),475-493.‏ https://doi.org/10.22034/chemm.2022.335815.1468.

Al-Daffay, R.K.; Al-Hamdani, AA. Synthesis, Characterization, and thermal analysis of a new acidic azo ligand's metal complexes. Baghdad Science Journal 2022, 19(3),121-133.

https://doi.org/10.21123/bsj.2022.6709.

Al Zoubia, W.; Al-Hamdani, AAS.; Kaseem, M. Synthesis and antioxidant activities of Schiff bases and their complexes: A review. Applied Organometallic chemistry 2016, 30(10),810-817.

https://doi.org/10.1002/aoc.3506.

Samy, M.E.; Moamen S.R.; Fawziah A.A.;Reham Z.H. Situ neutral system synthesis, spectroscopic, and biological interpretations of magnesium(II), calcium(II), chromium(III), zinc(II), copper(II) and selenium (IV) sitagliptin complexes. Int J Environ Res Public Health 2021, 18(8030),1-19. https://doi. 10.3390/ijerph18158030.

Al Zoubi, W.; Al-Hamdani, A.A.S.; Ko, Y.G. Schiff bases and their complexes:Recent progress in thermal analysis. Separation Science and Technology 2017, 52(6),1052-1069.

https://doi.10.1080/01496395.2016.1267756.

Al Zoubi, W.; Al-Hamdani, A.A.S., Widiantara, I.P.; Hamoodah, R.G.; Ko,Y.G. Theoretical studies and antibacterial activity for Schiff base complexes. Journal of Physical Organic Chemistry 2017, 30(6), e3707. https://doi. 10.1002/poc.3707.

Al Zoubi, W.; Al-Hamdani, A.A.S.; Ahmed, S.D.; Ko, Y.G. Synthesis, characterization, and biological activity of schiff bases metal complexes. Journal of Physical Organic Chemistry 2018, 31(2),e3752. https://doi. 10.1002/poc.3752.

Abdulrazzaq, A.G.; Al-Hamdani, A.A.S. Cr (III), Fe (III), Co (II) and Cu (II) metal ions complexes with azo compound derived from 2-hydroxy quinolin synthesis, characterization, thermal study and antioxidant activity. Ibn AL-Haitham Journal For Pure and Applied Sciences 2023, 36(3),214-230.‏ https://doi.org/10.30526/36.3.3068.

Obaid, S.M.H.; Jarad, A.J.; Al-Hamdani, A.A.S. Synthesis, characterization and biological activity of mixed ligand metal saltscomplexes with various ligands. Journal of Physics: Conference Series 2020, 1660(1),12028. https://doi.10.1088/1742-6596/1660/1/012028.

Keshavayya, J.; Pushpavathi, I.; Keerthikumar, C.T.; Maliyappa, M.R.;Ravi, B.N. Synthesis, characterization, computational and biological studies of nitrothiazole incorporated heterocyclic azo dyes. Journal of Structural Chemistry 2020, 31(4),1317-1329.‏ https://doi.10.1007/s11224-020-01493-0.

Moamen, S.R., Altalhi, T.; Safyah, B.B.; Ghaferah, H.A.; Kehkashan, A. New Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Zn(II), Cd(II),and Hg(II) gibberellate complexes: Synthesis, structure, and inhibitory activity against COVID-19 protease. Russian Journal of General Chemistry 2021, 91(5),890-896. https://doi.10.1134/S1070363221050194.

Jirjees, V.Y.; Al-Hamdani, A.A.S.;Wannas, N.M.; Abdall, F.R.; Dib, A.; Al Zoubi, W. Spectroscopic characterization for new model from Schiff base and its complexes. Journal of Physical Organic Chemistry 2021, 34(4),e4169.‏ https://doi.org/10.1002/poc.4169.

Abdullah, S.M.; Al-Hamdani, A.A.S.; Ibrahim, S.M.; Al-Zubaid, L.M.; Rashid, F.A. An evaluation of activity of prepared zinc nanoparticles with extract green plant in treatments of diclofenac, levofloxacin, and tetracycline in water. Journal of Medicinal and Chemical Sciences 2023, 6(6),1323-1335. https://doi.org/10.26655/JMCHEMSCI.2023.6.12.

Maliyappa, M.R..;Keshavayya, J.; Mallikarjuna, N.M.; Krishna, PM.; Shivakumara, N.; Sandeep, T.; Nazrulla, M.A. Synthesis, characterization, pharmacological and computational studies of 4, 5, 6, 7-tetrahydro-1,3-benzothiazole incorporated azo dyes. Journal Molecular Structure, 2019, 1179,630-641. https://doi.10.1016/j.molstruc.2018.11.041.

Kareem, M.J.; Al-Hamdani, A.A.S.; Ko, Y.G.; Al Zoubi, W.; Mohammed, S.G. Synthesis, characterization, and determination antioxidant activities for new schiff base complexes derived from 2-(1H-indol-3-yl)-ethylamine and metal ion complexes. Journal of Molecular Structure 2023, 20, 319827. https://doi.10.1016/j.molstruc.2020.129669.

Al Zoubi, W.; Al-Hamdani, A.A.S.; Sunghun, B., Ko, Y.G. A review on TiO2-based composites for superior photocatalytic activity. Reviews in Inorganic Chemistry-De Gruyter 2021, 234,108863. https://doi.10.1515/revic-2020-0025.

Hamza, I.S.;Mahmmoud, W.A.; Al-Hamdani, A.A.; Ahmed, S.D.; Allaf, A.W.; Al Zoubi, W. Synthesis, characterization, and bioactivity of several metal complexes of (4-Amino-N-(5-methyl-isaxazol-3-yl)-benzenesulfonamide). Inorganic Chemistry Communications 2022, 144,109776.

https://doi.org/10.1016/j.inoche.2022.109776.

Al-Hamdani, A.A.S.; Al-Alwany, T.A.M.; Mseer, M.A.; Fadhel, A.M.; Al-Khafaji, Y.F. Synthesis, characterization, spectroscopic, thermal and biological studies for new complexeswith N1, N2-bis (3-hydroxyphenyl) oxalamide. Egyptian Journal of Chemistry 2022, 8,8.

https://doi.10.21608/EJCHEM.2022.144403.6297.

Kareem, M.J.; Al-Hamdani, A.A.S.; Jirjees, V.Y.; Khan, M.E.; Allaf, A.W.; Al Zoubi, W. Preparation, spectroscopic study of Schiff base derived from dopamine andmetal Ni(II),Pd(II), and Pt(IV) complexes,and activity determination asantioxidants. Journal of Physical Organic Chemistry 2020, e4156. https://doi.10.1002/poc.4156.

Reda, S.M.; Al-Hamdani, A.A.S. Mn (II), Fe (III), Co (II) and Rh (III) complexes with azo ligand: Synthesis, characterization, thermalanalysis and bioactivity. Baghdad Science Journal 2022, 133, 511-523. https://doi.org/10.21123/bsj.2022.7289.

Al-Daffay, R.K.H.; Al-Hamdani, A.A.S.; Al Zoubi, W. Synthesis, characterization and thermal analysis of Cu (II), Co (II), Ru( III) and Rh(III) complexes of a new acidic ligand. Ibn Al-Haitham Journal for Pure and Applied Sciences 2023, 36(4),321-337. https://doi.org/10.30526/36.4.3047.

Obaid, S.M.H.; Sultan, J.S.; Al-Hamdani, A.A.S. Synthesis, characterization and biological efficacies from some new dinuclear metal complexes for base 3-(3,4-dihydroxy-phenyl)-2-[(2-hydroxy-3-methylperoxy-benzylidene)-amino]-2-methyl propionic acid. Indones Journal of Chemistry 2020, 20(6), 1311-1322. https://doi.10.22146/ijc.49842.

Al-Hamdani, A.A.S.; Al Zoubi, W. New metal complexes of N3 tridentate ligand: Synthesis, spectral studies and biological activity. Spectrochim Acta A Mol Biomol Spectrosc 2015, 137,75-89. https://doi.10.1016/j.saa.2014.07.057.

Al Zoubi, W.; Al‐Hamdani, A.A.S; Ahmed, S.D.; Basheer, H.M.; Al‐Luhaibi, R.S.; Dib, A.; Ko, Y.G. Synthesis, characterization, and antioxidant activities of imine compounds. Journal of Physical Organic Chemistry 2018, 32,1-9. https://doi.org/10.1002/poc.3916.

Abdulrazzaq A.G., Al-Hamdani, A.A.S. Ni2+, Pt4+, Pd2+, and Mn2+ metal ions complexes with azo derived from quinolin-2-ol and 3-amino-N-(5-methylisoxazol-3-yl) benzenesulfonamide: Synthesis, characterization, thermal study, and antioxidant activity. Baghdad Sciences Journal 2023, 20(6),2207-2223. https://doi.org/10.21123/bsj.2023.7708.

Al-Hamdani, A.A.S., Abdulridha, M.Q. Synthesis, characterization of new metal complexes of Co(II), Cu(II), Cd(II) and Ru(III) from azo ligand 5- ((2-(1H-indol-2-yl) ethyl) diazinyl)- 2-aminophenol, thermal and antioxidant studies. Baghdad Science Journal 2023, 20(5),1964-1975.

https://doi.org/10.21123/bsj.2023.7629.

Abdulrazzaq, A.G., Al-Hamdani, A.A. SCr (III), Fe (III), Co (II) and Cu (II) metal ions complexes with azo compound derived from 2-hydroxy quinolin synthesis, characterization, thermal study and antioxidant activity. Ibn AL-Haitham Journal For Pure and Applied Sciences 2023, 36(3),214-230. https://doi.org/10.30526/36.3.3068.