Synthesis and Characterization of N2O2 Type Schiff Base Ligand with Salicylaldehyde Derivate and Its Metal Complexes

Yıl 2024, Cilt: 11 Sayı: 3, 1091 - 1098

Sümeyra Tuna Yıldırım

https://doi.org/10.18596/jotcsa.1405238

Öz

Schiff bases and their metal complexes, which play a role in various biological processes, are one of the most important classes of organic and inorganic compounds. Due to their high use in the field of health, it is important to introduce these compounds into the literature through synthesis and research studies. In this study a new Schiff base ligand was synthesized by the reaction of 4-diethylamino-2-hyrdoxybenzaldehyde with o-aminophenol. This ligand was used to prepare Co(II), Ni(II), Cu(II) and Zn(II) complexes. The structural characterization of the synthesized ligand and metal complexes was elucidated by various spectroscopic and thermal analysis methods such as FT-IR, 1H-NMR, 13C-NMR, UV-Vis., XRD, SEM and TGA. As a result of these characterization studies, it was determined that the synthesized Schiff base acted as an N2O2 type tetradentate ligand and that the metal ions were bound to the ligand via phenolic oxygen and azomethine nitrogen.

Anahtar Kelimeler

İmine, Ligand, Metal Complex, Schiff Base, Structural Characterization

Kaynakça

• 1. Kajal A, Bala S, Kamboj S, Sharma N, Saini V. Schiff Bases: A Versatile Pharmacophore. J Catal [Internet]. 2013 Aug 27;2013:93512. Available from: <URL>.
• 2. Ashraf T, Ali B, Qayyum H, Haroone MS, Shabbir G. Pharmacological aspects of schiff base metal complexes: A critical review. Inorg Chem Commun [Internet]. 2023 Apr 1;150:110449. Available from: <URL>.
• 3. Kanagavalli A, Jayachitra R, Thilagavathi G, Padmavathy M, Elangovan N, Sowrirajan S, et al. Synthesis, structural, spectral, computational, docking and biological activities of Schiff base (E)-4-bromo-2-hydroxybenzylidene) amino)-N-(pyrimidin-2-yl) benzenesulfonamide from 5-bromosalicylaldehyde and sulfadiazine. J Indian Chem Soc [Internet]. 2023 Jan 1;100(1):100823. Available from: <URL>.
• 4. Juyal VK, Pathak A, Panwar M, Thakuri SC, Prakash O, Agrwal A, et al. Schiff base metal complexes as a versatile catalyst: A review. J Organomet Chem [Internet]. 2023 Oct 15;999:122825. Available from: <URL>.
• 5. Berhanu AL, Gaurav, Mohiuddin I, Malik AK, Aulakh JS, Kumar V, et al. A review of the applications of Schiff bases as optical chemical sensors. TrAC Trends Anal Chem [Internet]. 2019 Jul 1;116:74–91. Available from: <URL>.
• 6. Antony R, Arun T, Manickam STD. A review on applications of chitosan-based Schiff bases. Int J Biol Macromol [Internet]. 2019 May 15;129:615–33. Available from: <URL>.
• 7. Kamel RM, Shahat A, Anwar ZM, El-Kady HA, Kilany EM. A novel sensitive and selective chemosensor for fluorescent detection of Zn2+ in cosmetics creams based on a covalent post functionalized Al-MOF. New J Chem [Internet]. 2021;45(18):8054–63. Available from: <URL>.
• 8. Pervaiz M, Sadiq S, Sadiq A, Younas U, Ashraf A, Saeed Z, et al. Azo-Schiff base derivatives of transition metal complexes as antimicrobial agents. Coord Chem Rev [Internet]. 2021 Nov 15;447:214128. Available from: <URL>.
• 9. Jarrahpour AA, Motamedifar M, Pakshir K, Hadi N, Zarei M. Synthesis of novel azo schiff bases and their antibacterial and antifungal activities. Molecules [Internet]. 2004 Sep 30;9(10):815–24. Available from: <URL>.
• 10. Talebi A, Salehi M, Khaleghian A, Kubicki M. Evaluation of anticancer activities, apoptosis, molecular docking, and antioxidant studies of new Ni(II), VO(IV), Cu(II) and Co(III) Schiff base complexes. Inorganica Chim Acta [Internet]. 2023 Feb 1;546:121296. Available from: <URL>.
• 11. Kursunlu AN, Guler E, Sevgi F, Ozkalp B. Synthesis, spectroscopic characterization and antimicrobial studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with Schiff bases derived from 5-bromo-salicylaldehyde. J Mol Struct [Internet]. 2013 Sep 24;1048:476–81. Available from: <URL>.
• 12. Bhagat S, Sharma N, Chundawat TS. Synthesis of some salicylaldehyde-based schiff bases in aqueous media. J Chem [Internet]. 2013 Jan 1;2013:909217. Available from: <URL>.
• 13. Maxim C, Pasatoiu TD, Kravtsov VC, Shova S, Muryn CA, Winpenny REP, et al. Copper(II) and zinc(II) complexes with Schiff-base ligands derived from salicylaldehyde and 3-methoxysalicylaldehyde: Synthesis, crystal structures, magnetic and luminescence properties. Inorganica Chim Acta [Internet]. 2008 Oct 1;361(14–15):3903–11. Available from: <URL>.
• 14. Naeimi H, Moradian M. Synthesis and characterization of nitro-Schiff bases derived from 5-nitro-salicylaldehyde and various diamines and their complexes of Co(II). J Coord Chem [Internet]. 2010 Jan 10;63(1):156–62. Available from: <URL>.
• 15. Maity D, Drew MGB, Godsell JF, Roy S, Mukhopadhyay G. Synthesis and characterization of Cu(II) complexes of tetradentate and tridentate symmetrical Schiff base ligands involving o-phenelenediamine, salicylaldehyde and diacetyl monoxime. Transit Met Chem [Internet]. 2010 Mar 9;35(2):197–204. Available from: <URL>.
• 16. dos Santos JE, Dockal ER, Cavalheiro ÉTG. Synthesis and characterization of Schiff bases from chitosan and salicylaldehyde derivatives. Carbohydr Polym [Internet]. 2005 May 25;60(3):277–82. Available from: <URL>.
• 17. Avsar G, Altinel H, Yilmaz MK, Guzel B. Synthesis, characterization, and thermal decomposition of fluorinated salicylaldehyde Schiff base derivatives (salen) and their complexes with copper(II). J Therm Anal Calorim [Internet]. 2010 Jul 11;101(1):199–203. Available from: <URL>.
• 18. Bouzerafa B, Aggoun D, Ouennoughi Y, Ourari A, Ruiz-Rosas R, Morallon E, et al. Synthesis, spectral characterization and study of thermal behavior kinetics by thermogravimetric analysis of metal complexes derived from salicylaldehyde and alkylamine. J Mol Struct [Internet]. 2017 Aug 15;1142:48–57. Available from: <URL>.
• 19. Shi L, Ge HM, Tan SH, Li HQ, Song YC, Zhu HL, et al. Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde. Eur J Med Chem [Internet]. 2007 Apr 1;42(4):558–64. Available from: <URL>.
• 20. Adesibikan AA, Emmanuel SS. Synthesis and characterization of Co(II) complex with a schiff base ligand derived from salicylaldehyde and 4-chloroaniline. Int J Nov Res Phys Chem Math [Internet]. 2023;10(2):12–7. Available from: <URL>.
• 21. Meenukutty MS, Mohan AP, Vidya VG, Viju Kumar VG. Synthesis, characterization, DFT analysis and docking studies of a novel Schiff base using 5-bromo salicylaldehyde and β-alanine. Heliyon [Internet]. 2022 Jun 1;8(6):e09600. Available from: <URL>.
• 22. Abdel-Latif SA, Hassib HB, Issa YM. Studies on some salicylaldehyde Schiff base derivatives and their complexes with Cr(III), Mn(II), Fe(III), Ni(II) and Cu(II). Spectrochim Acta Part A Mol Biomol Spectrosc [Internet]. 2007 Jul 1;67(3–4):950–7. Available from: <URL>.
• 23. Cimerman Z, Galešić N, Bosner B. Structure and spectroscopic characteristics of Schiff bases of salicylaldehyde with 2,3-diaminopyridine. J Mol Struct [Internet]. 1992 Nov 26;274(C):131–44. Available from: <URL>.
• 24. Singh VP, Singh S, Singh DP, Tiwari K, Mishra M. Synthesis, spectroscopic (electronic, IR, NMR and ESR) and theoretical studies of transition metal complexes with some unsymmetrical Schiff bases. J Mol Struct [Internet]. 2014 Jan 24;1058(1):71–8. Available from: <URL>.
• 25. Yousif E, Majeed A, Al-Sammarrae K, Salih N, Salimon J, Abdullah B. Metal complexes of Schiff base: Preparation, characterization and antibacterial activity. Arab J Chem [Internet]. 2017 May;10:S1639–44. Available from: <URL>.
• 26. Iftikhar B, Javed K, Khan MSU, Akhter Z, Mirza B, Mckee V. Synthesis, characterization and biological assay of Salicylaldehyde Schiff base Cu(II) complexes and their precursors. J Mol Struct [Internet]. 2018 Mar 5;1155:337–48. Available from: <URL>.
• 27. Rajasekar M, Sreedaran S, Prabu R, Narayanan V, Jegadeesh R, Raaman N, et al. Synthesis, characterization, and antimicrobial activities of nickel(II) and copper(II) Schiff-base complexes. J Coord Chem [Internet]. 2010 Jan 10;63(1):136–46. Available from: <URL>.
• 28. Cristóvão B. Spectral, thermal and magnetic properties of Cu(II) and Ni(II) complexes with Schiff base ligands. J Serbian Chem Soc [Internet]. 2011;76(12):1639–48. Available from: <URL>.
• 29. Chandra S, Kumar U. Spectral and magnetic studies on manganese(II), cobalt(II) and nickel(II) complexes with Schiff bases. Spectrochim Acta Part A Mol Biomol Spectrosc [Internet]. 2005 Jan 1;61(1–2):219–24. Available from: <URL>.
• 30. Liu J, Wu BW, Zhang B, Liu Y. Synthesis and characterization of metal complexes of Cu(II), Ni(II), Zn(II), Co(II), Mn(II) and Cd(II) with tetradentate schiff bases. Turkish J Chem [Internet]. 2006 Jan 1;30(1):41–8. Available from: <URL>.
• 31. Taha ZA, Ajlouni AM, Al-Hassan KA, Hijazi AK, Faiq AB. Syntheses, characterization, biological activity and fluorescence properties of bis-(salicylaldehyde)-1,3-propylenediimine Schiff base ligand and its lanthanide complexes. Spectrochim Acta Part A Mol Biomol Spectrosc [Internet]. 2011 Oct 15;81(1):317–23. Available from: <URL>.
• 32. Neelakantan MA, Marriappan SS, Dharmaraja J, Jeyakumar T, Muthukumaran K. Spectral, XRD, SEM and biological activities of transition metal complexes of polydentate ligands containing thiazole moiety. Spectrochim Acta Part A Mol Biomol Spectrosc [Internet]. 2008 Nov 15;71(2):628–35. Available from: <URL>.
• 33. Deswal Y, Asija S, Dubey A, Deswal L, Kumar D, Kumar Jindal D, et al. Cobalt(II), nickel(II), copper(II) and zinc(II) complexes of thiadiazole based Schiff base ligands: Synthesis, structural characterization, DFT, antidiabetic and molecular docking studies. J Mol Struct [Internet]. 2022 Apr 5;1253:132266. Available from: <URL>.
• 34. Khan MI, Khan A, Hussain I, Khan MA, Gul S, Iqbal M, et al. Spectral, XRD, SEM and biological properties of new mononuclear Schiff base transition metal complexes. Inorg Chem Commun [Internet]. 2013 Sep 1;35:104–9. Available from: <URL>.
• 35. Shakir M, Hanif S, Sherwani MA, Mohammad O, Al-Resayes SI. Pharmacologically significant complexes of Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) of novel Schiff base ligand, (E)-N-(furan-2-yl methylene) quinolin-8-amine: Synthesis, spectral, XRD, SEM, antimicrobial, antioxidant and in vitro cytotoxic studies. J Mol Struct [Internet]. 2015 Jul 15;1092:143–59. Available from: <URL>.