ADVANCED JOURNAL OF CHEMISTRY RESEARCH
Integrity Research Journals

Model: Open Access/Peer Reviewed
DOI: 10.31248/AJCR
Start Year: 2022
Email: ajcr@integrityresjournals.org


Synthesis, characterization and biological profiles of Schiff base aldimines derived from N-N1-Diphenyl-O-Pyrol-6-Methyleneacetate and its Cu2+ and Fe2+ complexes

https://doi.org/10.31248/AJCR2023.006   |   Article Number: 91EECDD32   |   Vol.1 (2) - August 2023

Received Date: 11 May 2023   |   Accepted Date: 09 June 2023  |   Published Date: 30 August 2023

Authors:  Iorungwa, M. S.* , Atagher, J. A. , Shimaibo, P. T. and Nanev, J. D.

Keywords: 2-phenylglycinemethyesterhydrochloride, Esculentum spp., Schiff base, Meloidogyne incognita, pyrol-2-carbaldehyde.

The aldimine ligand N-N1-diphenyl-o-pyrol-6-methyleneacetate (PPA) was prepared by a condensation reaction between 2-phenylglycinemethyesterhydrochloride and pyrol-2-carbaldehyde which was used to synthesize transition metal complexes of Cu(II) and Fe(II) employing the microwave assisted technique. The ligand and complexes were characterized by FTIR, UV, XRD, and magnetic susceptibility measurements. Spectral results which had PPA – Cu (46.619 cm-1) and PPA – Fe (43.859 cm-1) revealed complexation arising from the nitrogen of the azomethine group. The UV and magnetic susceptibility confirmed the probable geometries of Cu(II) and Fe(II) complexes to be octahedral with magnetic moments of 1.66 and 1.11 B.M respectively. Crystallographic diffraction pattern revealed the unit cell dimension of a (7.9Å), b(7.4Å), c(7.0Å), α(90o), β(90o), γ(90o) for Fe and a(4.3 Å), b(3.8Å), c(4.46Å), α(90o), β(90o), γ(90o) for Cu(II) aligning with orthorhombic crystal system. Molar conductance measurement of 717 and 229 Ω-1cm-2mol-1 PPA – Cu and PPA – Fe respectively indicated that the complexes are electrolytic in nature. The metal complexes showed higher inhibiting potential compared to the free ligand when tested against the root knot nematode Meloidogyne incognita present in the crop Esculentum spp implying that the complexes can be used as nematicides.

Akter, J., Hanifl, M. A., Saidul, M. I., Masuqul, M. H., Seung, H. L., & Laila, A. B. (2017). Synthesis, Characterization and antimicrobial activity of mixed ligand complexes of Mn (II) and Zn(II) with Phthalic Acid or Siccinic Acid and Heterocyclic Amines. Der Chemical Sinica. 8(1),166-174.
 
Anant, P., & Devjan, A. (2011). Application of Schiff bases and their complexes. A review. International Journal of ChemTech Research, 3(4), 1891-1896.
 
Atagher, J. A. (2021). Synthesis, characterization and nematicidal studies of transition metal complexes and azomethines obtained from 2-phenylglycinemethylesterhydrochloride and some selected aldehydes. .Ph.D thesis submitted to the Department of Chemistry, Joseph Sarwuan Tarka University Makurdi. Pp. 1-217.
 
Bal, M., Ceyhan, G., Avar, B., Kose, M., Kayraldiz, A., & Kurtoglu, M. (2014). Synthesis and X-ray diffraction, electrochemical and genotic properties of a new azo-Schiff base and its metal complexes. Turkish Journal of Chemistry, 38, 222-241.
Crossref
 
Bansal, N., & Dave, S. (2013). Analgesic and anti-inflammatory activities of Schiff base metal complexes- A review. International Journal of Basic and Applied Chemical Science, 3(1), 31-40.
 
Chairany, S., Sudibyo M, & Abdul R (2018). Application of Fourier Transform Infrared (FTIR) spectroscopy coupled with multivariate calibration for quantitative analysis of curcuminoid in tablet dosage form. Journal of Applied Pharmaceutical Science, 8(8), 151-156.
Crossref
 
Chandraleka, G., Chandramohan, D., Dhanasekaran, D., & Panneerelvan, A. (2011). Antifungal activity of amino acid Schiff base copper (II) complexes with phenanthroline and bipyridyl. International Journal of Chemical and Analytical Science, 2(10), 1235-1240.
 
Da Silva, C. M., da Silva, D. L., Modolo, L. V., Alves, R. B., de Resende, M. A., Martins, C. V., & de Fátima, Â. (2011). Schiff bases: A short review of their antimicrobial activities. Journal of Advanced Research, 2(1), 1-8.
Crossref
 
Deshpande, V. G., & Seema, I. H. (2016). X-ray diffraction study of transition metal complexes of heterocyclic Schiff bases. Journal of Chemistry and Chemical Sciences, 6(10), 934-944.
 
Ekta, Utreja, D., & K Dhillon, N. (2014). Synthesis of metal complexes of schiff bases and their nematicidal activity against root knot nematode Meloidogyne incognita. Letters in Organic Chemistry, 11(2), 116-125.
Crossref
 
Fei-Ran, L., Xin.Z., Dong-Dong, W., Zhi-Ng. X., & Ying-Ke, M. (2014). Synthesis, spectral, thermal stability and bacterial activity of Schiff bases derived from alanine and threonine and their complexes. Journal of Chemical and Pharmaceutical Research, 7(8), 792-803.
 
Gnanaprakash, S., Madhumtha, B., Jayapradha, C., Devipriya, S., & Kalaiarasan, P. (2016). Identification of resistance in mulberry, Morus SPP. For Root knot nematode, Meloidogyne incognita. International Journal of Plant Science, 2(2), 262-264.
Crossref
 
Goreci, C.Y., Zulal, D and Nilay A. (2016). Green synthesis of new amino acid Schiff base and their biological activities. Journal of the Turkish Chemical Society, 3(3), 15-26.
Crossref
 
Gülcan, M., Sönmez, M., & Berber, I. (2012). Synthesis, characterization, and antimicrobial activity of a new pyrimidine Schiff base and its Cu (II), Ni (II), Co (II), Pt (II), and Pd (II) complexes. Turkish Journal of Chemistry, 36(1), 189-200.
Crossref
 
Hayat, K. A., Yerramilli, S., Adrien, D., Terry L. A., Daria, C. B., & Gregory, S. P. (2020). Experimental methods in chemical engineering: X-ray diffraction spectroscopy-XRD. Canadian Journal of Chemical Engineering, 98,1255-1266.
Crossref
 
Hossein, N., & Mohsen, M. (2010). Synthesis and characterization of nitro-Schiff bases derivedfrom 5-nitro-salicylaldehyde and various diamines and their complexes of Co(II). Journal of Coordination Chemistry, 63(1), 156-162.
Crossref
 
Iorungwa, M. S., Mamah, C. L., & Wuana, R. A. (2019). Synthesis, characterization, kinetic, thermodynamic and antimicrobial activity studies of complexes of Cd (II), Cr (III), and Zr (IV) derived from benzaldehyde and ethylenediamine. ChemSearch Journal, 10(2), 10-24.
 
Iorungwa, M. S., Ugama A. G., Wuana A. R., Amua, Q. M., Tivkaa, J., Iorungwa, P. D., & Surma, N. (2021b). Nematicidal activity studies of Cu2+ and Zn2+ complexes with some aldimine ligands against Meloidogyne arenaria: A root knot nematode of Arachis hypogea. International Journal of New Chemistry, 8(3), 365-385.
 
Iorungwa, M. S., Wuana, A. R, Tyagher, L., Agbendeh, Z. M, Iorungwa P. D, Surma, N., & Amua, Q. M. (2020). Synthesis, characterization, kinetics, thermodynamics and nematicidal studies of Sm(III), Gd(III) and Nd(III) Schiff base complexes. ChemSearch Journal, 11(2), 24-34.
 
Iorungwa, M. S., Wuana, R. A., Chahul, H. F., Atagher, J. A., & Ona, J. I. (2021a). Synthesis, characterization and nematicidal studies of Cu2+ and Fe2+ complexes of Schiff base derived from 2-phenylglycinemethylesterhydrochloride and benzaldehyde. FUAM Journal of Pure and Applied Science, 1(2), 99-109.
 
Jisha, M. J., & Isaac, S. R. (2017). Synthesis and characterization of Schiff base complexes of Cu(II), Ni(II), Co(II) complexes of Schiff base derived from furan 3-carboxaldehyde and 3- amino pyridine. International Journal of Scientific and Research Publications, 7(10):10-19.
Crossref
 
Karakaya, C., Bede, B., & Cicek, E. (2016). Novel metal (II) complexes with bidendatwe Schiff base ligand: Synthesis, spectroscopic properties and dye decolorization functions. Proceedings of the 50th Zakopane School of Physics, Zakopane, Poland, 129(2),1208-2012.
Crossref
 
Mahapatra, B. B., Mishra, R. R., & Sarangi, A. K. (2016). Synthesis, characterisation, XRD, molecular modelling and potential antibacterial studies of Co (II), Ni (II), Cu (II), Zn (II), Cd (II) and Hg (II) complexes with bidentate azodye ligand. Journal of Saudi Chemical Society, 20(6), 635-643.
Crossref
 
Narendra, K. C., & Parashuram, M. (2013). Synthesis, characterization and molecular modelling of Ni(II) and cu(II) complexes with Schiff base derived from 1H-benzo[d]imidazole-4-amine and 2-hydroxy benzaldehyde. Archives of Applies Science Research, 5(5), 191-197.
 
Nwabueze, J. N., & Salawu, O. W. (2012). Complexes of Ni(II), and Cu(II) sulphates with keto and enol forms of isobutryl acetic acid, 4-amino benzoic acid and 4-cyno benzoic acid hydazide. Advances in Pure and Applied Chemistry, 1(2), 1-9.
 
Ruanpanun, P., Laatsch, H., Tangchitsomkid, N., & Lumyong, S. (2011). Nematicidal activity of fervenulin isolated from a nematicidal actinomycete, Streptomyces sp. CMU-MH021, on Meloidogyne incognita. World Journal of Microbiology and Biotechnology, 27, 1373-1380.
Crossref
 
Yokeswari, N. P., Ananthi, P., & Shanmuga, P. D. (2019). Synthesis, Characterization and Biological activities of Schiff base Ligands and its Metal Complexes. International Journal of Advanced Scientific Research and Management, 4,77-81.