Synthesis, Spectral Identification, Thermal and Antioxidant Studies for Ni (II), Pd (II), Pt (IV) and Au (III) Complexes With New Azo Ligand Derivatives from Tryptamine

Main Article Content

Myasim Qasim Abdulridha
Abbas Ali Salih Al-Hamdani
Wail Al Zoubi

Abstract

In this study, a new Azo ligand 5-((2-(1H-indol-2-yl)ethyl)diazinyl)-2-aminophenol is synthesized from a reaction of Tryptamine with 2-aminophenol. The ligand and their metal ion complexes Ni(II), Pd(II) , Pt(IV) and Au(III) have been synthesized and characterized by various analytical techniques, including elemental microanalysis, metal content, chloride-containing, measurement of electrical conductivity, magnetic susceptibility, 1H and 13C-NMR, FT-IR, UV-Vis, mass spectra (MS), and thermal analysis (TGA and DSC) curves. The DCS curve was used to calculate the thermodynamic parameters ΔH, ΔS, and ΔG. The characterization results promote the metal complexes of azo ligand structures. The results indicate that the ligand behaves as a trident N, N, and O donor ligand for each and every produced complex, and the molar conductivity of all complexes indicates that none of the complexes were electrolytes. The antioxidant activity of the synthesized compounds was evaluated and determined against the DPPH radical (1.1-diphenyl-2-picrylhydrazyl) and compared to that of a standard natural antioxidant, gallic acid. The results show that the metal complexes are more effective at scavenging free radicals.

Article Details

How to Cite
Synthesis, Spectral Identification, Thermal and Antioxidant Studies for Ni (II), Pd (II), Pt (IV) and Au (III) Complexes With New Azo Ligand Derivatives from Tryptamine. (2023). Ibn AL-Haitham Journal For Pure and Applied Sciences, 36(4), 303-320. https://doi.org/10.30526/36.4.3059
Section
Chemistry

How to Cite

Synthesis, Spectral Identification, Thermal and Antioxidant Studies for Ni (II), Pd (II), Pt (IV) and Au (III) Complexes With New Azo Ligand Derivatives from Tryptamine. (2023). Ibn AL-Haitham Journal For Pure and Applied Sciences, 36(4), 303-320. https://doi.org/10.30526/36.4.3059

Publication Dates

References

Wannas, N.M.; Al-Hamdani, A.A.S.; Al-Zoubi, W. Spectroscopic Characterization for New Complexes with 2,2'- (5,5-dimethylcyclohexane-1,3- diylidene)bis(azan-1-yl-1-ylidene)dibenzoic acid. Journal of physical organic chemistry 2020, 33, 1-12.

Sonmez, M.; Sogukomerogullari, H.G.; Oztemel, F.; Berber, I. Synthesis and biological Evaluation of a Novel ONS Tridentate Schiff Base Bearing Pyrimidine Ring and Some Metal complexes, Medicinal Chemistry Research 2014, 23, 3451–3457.

Abdulrazzaq, A.G.; Al-Hamdani, A.A. 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 Science Journal.2023,20, 1-17.

Al-Daffay, R.K.; Al-Hamdani, A.A.S. Synthesis and Characterization of Some Metals Complexes with New Acidicazo Ligand 4-[(2-Amino-4-Phenylazo)-Methyl]-Cyclohexane Carboxylic Acid. Iraqi Journal of Science. 2022 ,31,3264-75.

Abdulrazzaq, A.G.; Al-Hamdani, A.AS.Some Metal Ions Complexes With Azo [4-((8- hydroxyquinolin-7- yl)-N(4-methylisoxazol-3-yl)benzenesulfonamide] Synthesis, Characterization, Thermal Study and Antioxidant Activity.journal of Medicinal and Chemical Sciences. 2023,6, 236-249

Al-Daffay, R.K.; Al-Hamdani, A.A. Synthesis, Characterization, and Thermal Analysis of a New Acidicazo Ligand's Metal Complexes. Baghdad Science Journal 2022,19(3),121-33.

Al Zoubi, W.; Vian, Y.J.; Veyan, T.S.; Al-Hamdani, A.A.S.; Suzan, D.A.; Yang, Gon Kim. Synthesis and Bioactivity Studies of Novel Schiff Bases and Their Complexes. Journal of physical organic chemistry 2019, e4004, 1-7.

Suleman, V.T.; Al-Hamdani, A.A.S.; Ahmed, S.D.; Jirjees, V.Y.; Khan, M.E.; Adnan, Dib Phosphorus Schiff Base Ligand and Its Complexes: Experimental and Theoretical Investigations. Applied organometallic chemistry 2020, 34(4), 1-16

Al Zoubi, W.; Al‐Hamdani, A.A.S.; Susan, D.A.; Hassan, M.B.; Al‐Luhaibi, R.S.A.; Adnan, Dib.; Young, G.K. Synthesis, Characterization, and Antioxidant Activities of Imine compounds. Journal of physical organic chemistry 2018, e3916, 1-9.

Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds; 5th ed. Wiley-Interscience, New York, 1997, Part A. P. 7-12.

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 2021, 1231, 1-30.

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 and Metal Ni (II), Pd (II), and Pt (IV) complexes, and Activity Determination as Antioxidants. Journal of physical organic chemistry 2020, 3, 1-15.

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, 1052- 1069.

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-methylisaxazol-3-yl)-benzenesulfonamide). Inorganic Chemistry Communications 2022 , 6, 109776.

Al Zoubi, W.; Mohamed, S.G.; Al-Hamdani, A.A.S.; Mahendradhany, A.P.; Ko, Y.G. Acyclic and Cyclic Imines and Their Metal Complexes: Recent Progress in Biomaterials and Corrosion Applications. RSC advances 2018,8, 23294-23318.

Mohamed, W.N.; Al-Hamdani, A.A.S.; Al Zoubi, W.Spectroscopic Characterization for New Complexes with 2, 2′-(5, 5-dimethylcyclohexane-1, 3-diylidene) bis (azan-1-yl-1-ylidene) Dibenzoic Acid. Journal of physical organic chemistry 2020,33, e4099.

Turan, N.; Buldurun, K.; Adiguzel, R.; Aras, A.; Turkan, F.; Bursal, E. Investigation of Spectroscopic, Thermal, and Biological Properties of FeII, CoII, ZnII, and RuII Complexes Derived from Azo Dye Ligand. Journal of Molecular Structure 2021, 15,130989

Kadhim, A.A.; Kareem, I.K.; Ali, A.A. Synthesis and Spectral Identification of New AzoSchiff Base Ligand Derivative from Aminobenzylamine and its Novel Metal Complexes with Cu (II), Zn (II) and Cd (II). Annals of the Romanian Society for Cell Biology 2021, 25,4596-607.

Mahdi, M.A.; Jasim, L.S.; Mohamed, M.H. Synthesis, Spectral and Biological Studies of Co (II), Ni (II) and Cu (II) Complexes with New Heterocyclic Ligand Derived from Azo-Dye. Pharmaceutical reviews 2021, 12,426-34.

Witwit, I.N.; Farhan, H.M.; Motaweq, Z.Y. Preparation of Mixed ligand Complexes of Heterocyclic Azo Quinoline Ligand and Imidazole Molecule with Some of Divalent Transition Ions and their Biological Activity Against Multi Drug Resistance Pathogenic Bacteria. InJournal of Physics: Conference Series 2021,1879,022064

Al-Bahadili, Z.R.; Al-Hamdani, A.A.S.; Rashid, F.A.; AlZubaidi, L.A.; Ibrahim, S.M. An Evaluation of the Activity of Prepared Zinc Nanoparticles with Extract of Alfalfa Plant in the Treatment of heavy metals. Baghdad Sci J. 2022, 19, 1399-1409.

Al-Zoubi, W.; Kim, M.J.; Yoon, D.K.; Al-Hamdani, A.A.; Kim, Y.G.; Young, G.K. Effect of Organic Compounds and Rough Inorganic Layer Formed by Plasma Electrolytic Oxidation on Photocatalytic Performance. J Alloys Compd. 2020, 15,153787.

Reda, S.M.; Al-Hamdani, A.A.S. Mn(II), Fe(III), Co(II) and Rh(III) complexes with azo ligand: Synthesis, characterization, thermal analysis and bioactivity. Baghdad Sci J. 2022, 20, 1399-1409.

Saeed, A.; AlNeyadi, S., Abdou, M. Anticancer Activity of Novel Schiff Bases and Azo Dyes Derived from 3-amino-4-hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione. Heterocyclic Communications.2020, 26,192 .

Suleman, V.;Al-Hamdani, A., Ahmed, S., Jirjees, V., Khan, M., Dib, A., Al Zoubi, W., Ko, Y. Phosphorus Schiff base ligand and its complexes: Experimental and theoretical investigations.Applied Organometallic Chemistry2020, 34, 5546 .

Al-Hamdani, A.; Al Zoubi, W. New Metal Complexes of N3 Tridentate Ligand: Synthesis, Spectral Studies and Biological Activity, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015, 137,75 .

Shaalan, N. Preparation, Spectroscopy, Biological Activities and Thermodynamic Studies of New Complexes of Some Metal Ions with 2-[5-(2-Hydroxy-Phenyl)- 1,3,4-Thiadiazol-2-Ylimino]-Methyl-Naphthalen-1-Ol], Baghdad Science Journal 2022, 19, 829 .

Silverstein, R.; Bassler, G. Spectrometric Identification of Organic Compounds. Journal of Chemical Education 1962, 39, 546.

Jirjees, V., Al‐Hamdani, A., Wannas, N., Dib, A., Al Zoubi W.Spectroscopic characterization for New Model from Schiff Base and Its Complexes, Journal of Physical Organic Chemistry 2021, 34,4169 .

Silverstein, R.; Webster, F.; Kiemle, D. Spectrometric Identification of Organic Compounds.7th ed. J W. A. INC, 2005 .

Obaid, S., Jarad, A., Al-Hamdani, A. Synthesis, Characterization and Biological Activity of Mixed Ligand Metal Salts Complexes with Various Ligands, Journal of Physics: Conference Serie, 2020,1660,012028 .

Al-Hamdani AAS, Al-Alwany TAM, Mseer MA, Fadhel AM, Al-Khafaji YF. Synthesis, Characterization, Spectroscopic, Thermal and Biological Studies for New Complexes with N1, N2-bis (3-hydroxyphenyl) Oxalamide.EgyptJ. of Chem. 2023, 66,223-235.

Wannas, N.; Al-Hamdani, A.AS, Al-Zoubi, W. Spectroscopic Characterization for New Complexes with 2,2'- (5,5-dimethylcyclohexane-1,3-diylidene)bis(azan-1-yl- 1-ylidene) dibenzoic acid.Journal of Physical Organic Chemistry 2020, 33, 4099 .

Moamen, S.; Altalhi, T., Bakare, S., Al-Hazmi, G., Alam, K. 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 Chemistry2021, 91, 890 .

Al Zoubi, W.; Al-Hamdani, A., Sunghun , B. A review on TiO2 Based Composites for Superior Photocatalytic Activity. Reviews in Inorganic Chemistry 2021, 41, 213 .

Blümich, B.; Blümich ,P., Pauly,Essential NMR. Springer International Publishing. 2019.

Mohammed, H. Synthesis, Identification, and Biological Study for Some Complexes of Azo Dye Having Theophylline, The Scientific World Journal 2021,9943763 .

Mohammed,S.;Al-Hamdani, A. Synthesis, Characterization, Thermal Analysis and Bioactivity of Some Transition Metals Complexes with New Azo Ligand, Chemical Methodologies 2022, 475-493.

.Obaid, S.;. Sultan, J., Al-Hamdani, A. 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, Indonesian Journal of Chemistry 2020, 20,1311 .

Al-Hamdani, A.A.S.; Balkhi, A.; Falah, A.; Shaker, S. Synthesis and Investigation of Thermal Properties of Vanadyl Complexes with Azo-Containing. Journal of Saudi Chemical Society, 2016, 20,487 .

Jirjees, V.; Suleman, V.; Al-Hamdani, A.; Ahmed, S. Preparation, Spectroscopic Characterization and Theoretical Studies of Transition Metal Complexes with 1-[(2-(1H-indol-3-yl) ethylimino) methyl] naphthalene-2-ol Ligand, Asian journal of chemistry2019, 31, 2430 .