Yeni sentezlenmiş naftaldimin-temelli tetraimin Schiff bazında fenol-keto tautomerliğinin, metal iyon bağlama ve serbest radikal süpürme özelliklerinin çalışılması

Abstract

Bu çalışmada, sırasıyla D₁ diimin Schiff bazının sentezlenmesi, bu Schiff bazının nitro grubunun amino grubuna indirgenmesi ve amino grubunun 2-hidroksi-1-naftaldehit ile etkileştirilmesi ile yeni dört imin grubu bulunan Schiff bazı (T₁) sentezlendi.  Bileşik çeşitli spektroskopik teknikler ile karakterize edildi.  Schiff bazındaki (T₁) fenol-keto tautomerliği farklı çözücü ve ortamlarda UV-GB spektrumları ile incelendi.  T₁ ile bazı metal iyonları Cr³⁺, Fe³⁺, Ni²⁺, Zn²⁺, Cu²⁺, Co²⁺, Pb²⁺, Ag⁺ and Ba²⁺ arasındaki bağlanma etkileşimi DMF-HEPES tampon karışımında (v/v, 1:1) UV–GB spektrofotometrisi ile belirlendi.  Sonuçlar tercih edilen bağlanmanın Cu²⁺, Co²⁺ ve Fe³⁺ iyonları ile olduğunu gösterdi.  Cu²⁺, Co²⁺ and Fe³⁺ iyonu varlığında, T₁ çözeltisinin rengi sarıdan renksiz olacak şekilde değişti. T₁ ile Cu²⁺, Co²⁺ ve Fe³⁺ iyonları arasında 1:1 bağlanma olduğu Job’s eğrisi yönteminden belirlendi.  Bağlanma sabitleri (K_a) Cu²⁺, Co²⁺ ve Fe³⁺ iyonları için sırasıyla Benesi–Hildebrand eşitliğinden 1.22 x 10⁴ M^-1, 1.62 x 10⁴ M^-1 ve 5.79 x 10⁴ M^-1 olarak hesaplandı.  Ayrıca, T₁’in DPPH radikallerine karşı potansiyel bir süpürücü olduğu, yüzde 50 süpürme konsantrasyon değerinin standard askorbik asitten çok az büyük olduğu belirlendi. 

Keywords

• Schiff bazları
• tautomerlik
• kolorimetrik sensörler
• serbest radikal süpürme aktivitesi

Studies on phenol-keto tautomerism, metal ion binding, and free radical scavenging properties of newly synthesized naphthalene-based tetraimine Schiff base

Abstract

In this study, a new tetraimine Schiff base (T₁) was obtained by the synthesis of diimine Schiff base (D₁), the reduction of nitro group of this Schiff base to amino group and the reacting of amino group with 2-hydroxy-1-naphthaldehyde, respectively. It was characterized by various spectroscopic techniques. The phenol-keto tautomerism of Schiff base (T₁) was investigated by UV–vis spectra in different solvents and media. The binding interaction between T₁ and metal ions, i.e., Cr³⁺, Fe³⁺, Ni²⁺, Zn²⁺, Cu²⁺, Co²⁺, Pb²⁺, Ag⁺ and Ba²⁺ was confirmed in DMF-HEPES buffer (v/v, 1:1) by UV–vis spectroscopy. It showed the favorable coordination toward Cu²⁺, Co²⁺ and Fe³⁺ ions. In the presence of Cu²⁺, Co²⁺ and Fe³⁺ ions, yellow color of T₁ solution changed to colorless. The 1:1 binding stoichiometry between T₁ and Cu²⁺, Co²⁺, Fe³⁺ ions was established using Job’s plot. The binding constants (Ka) were calculated to be 1.22 x 10⁴ M^-1, 1.62 x 10⁴ M^-1 and 5.79 x 10⁴ M^-1 for Cu²⁺, Co²⁺ and Fe³⁺ ions, respectively, by Benesi–Hildebrand equation. In addition, T₁ was also found to be potent scavenger of DPPH radicals with half-maximal scavenging concentration (SC₅₀) value less high than that of the standard, ascorbic acid.

Keywords

• Schiff bases
• tautomerism
• colorimetric sensors
• free radical scavenging activity

References

1. Atta, A.M., Shaker, N.O., and Maysour N.E., Influence of the molecular structure on the chemical resistivity and thermal stability of cured Schiff base epoxy resins, Progress in Organic Coatings, 56, 100–110, (2006).
2. Mishra, L., Bindu, K., and Bhattacharya S., Spectroscopic studies, structure simulation and phenol binding property of dimetallocyclophanes derived from tetradentate Schiff bases, Inorganic Chemistry Communications, 7, 777–780, (2004).
3. Zhang, Y., and Lu Z-H., A theoretical study on N,N’-disalicylidene-p-phenylenediamine (BSP) for the multi-component material design, Materials Chemistry and Physics, 57, 253-259, (1999).
4. Kumari, N., Prajapati, R., and Mishra, L., Reactivity of M(en)Cl2 (M = PdII/PtII, en= 1,2-diaminoethane) with N,N’-bis(salicylidene)-p-phenylenediamine: Binding with hexafluorobenzene, Polyhedron, 27, 241–248, (2008).
5. Djouhra, A., Ali, O., Ramiro, R-R., and Emilia, M., A selective naked-eye chemosensor derived from 2-methoxybenzylamine and 2,3-dihydroxybenzaldehyde-synthesis, spectral characterization and electrochemistry of its bis-bidentates Schiff bases metal complexes, Spectrochimica Acta Part A, 184, 299-307, (2017).
6. Mesbah, M., Douadi, T., Sahli, F., Issaadi, S., Boukazoula, S., and Chafaa, S., Synthesis, characterization, spectroscopic studies and antimicrobial activity of three new Schiff bases derived from heterocyclic moiety, Journal of Molecular Structure, 1151, 41-48, (2018).
7. Sztanke, K., Maziarka, A., Osinka, A., and Sztanke, M., An insight into synthetic Schiff bases revealing antiproliferative activities in vitro, Bioorganic and Medicinal Chemistry, 21, 3648–3666, (2013).
8. Kirubavathy, S.J.,Velmurugan, R., Karvembu, R., Bhuvanesh, N.S.P., Enoch, Israel V.M.V.P., Selvakumar, M., Premnath, D., and Chitra, S., Structural and molecular docking studies of biologically active mercaptopyrimidine Schiff bases, Journal of Molecular Structure, 1127, 345–354, (2017).

9. Karrouchi, K.,Chemlal, L., Taoufik, J., Cherrah, Y., Radi, S., El Abbes Faouzi, M., and Ansar, M., Synthesis, antioxidant and analgesic activities of Schiff bases of 4-amino-1,2,4-triazole derivatives containing a pyrazole moiety, Annales Pharmaceutiques Françaises, 74, 6, 431-438, (2016).
10. Kumar, K.S., Ganguly, S., Veerasamy, R., and De Clercq, E., Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3)H-ones, European Journal of Medicinal Chemistry, 45, 11, 5474-5479, (2010).
11. Murtaza, S., Akhtar, M.S., Kanwal, F., Abbas, A., Ashiq, S., and Shamim, S., Synthesis and biological evaluation of schiff bases of 4-aminophenazone as an anti-inflammatory, analgesic and antipyretic agent, Journal of Saudi Chemical Society, 21, 1, 359-372, (2017).
12. Durgun, M., Turkmen, H, Ceruso, M., and Supuran, C.T., Synthesis of Schiff base derivatives of 4-(2-aminoethyl)-benzenesulfonamide with inhibitory activity against carbonicanhydrase isoforms I, II, IX and XII, Bioorganic and Medicinal Chemistry Letters, 25, 11, 2377-2381, (2015).
13. Vanco, J., Marek, J., Travnicek, Z., Racanska, E., Muselik, J., and Svajlenova, O., Synthesis, structural characterization, antiradical and antidiabetic activities of copper(II) and zinc(II) Schiff base complexes derived from salicylaldehyde and beta-alanine, Journal of Inorganic Biochemistry, 102, 595- , (2008).
14. Sridhar, S.K., Pandeya, S.N., Stables, J.P., and Ramesh, A., Anti convulsant activity of isatinhydrazones, Schiff and Mannich bases of isatin derivatives, European Journal of Pharmaceutical Sciences, 16, 129–132, (2002).
15. Samadhiya, S., and Halve, A., Synthetic Utility of Schiff Bases as Potential Herbicidal Agents, Oriental Journal of Chemistry, 17, 119-, (2001).
16. H. El Ashry, E.S., El Nemra, A., Essawy, S.A., and Ragaba, S., Corrosion inhibitors part 31: quantum chemical studies on the efficiencies of some aromatic hydrazides and Schiff bases as corrosion inhibitors of steel in acidic medium, Arkivoc, xi, 205-220, (2006).
17. Pandeya, S.N., Yogeeswari, P., Sriram, D., De Clercq, E., Pannecouque, C., and Witvrouw, M., Chemotherapy, 45, 192–196, (1999).
18. Goomer, N.C., Kulkarni, P.V., Constantinescu, A., Antich, P., Parkey, R.W., and Corbett, J.R., Synthesis and evaluation of technetium-99m monocationic mixed ligand complexes of phenylsubstituted/condensed tetradentate schiff's bases and trimethylphosphine, Biology, 19, 679-684, (1992).
19. Asadi, Z., and Nasrollah, N., The effect of metal and substituent on DNA binding, cleavage activity, and cytotoxicity of new synthesized Schiff base ligands and Zn(II) complex, Journal of Molecular Structure, 1147, 582-593, (2017).
20. Beyazit, N., Çakmak, D., and Demetgül, C., Chromone-based Schiff base metal complexes as catalysts for catechol oxidation: Synthesis, kinetics and electrochemical studies, Tetrahedron, 73, 19, 2774-2779, (2017).
21. Magro, A, Crociani, L., Prinzivalli, C., Vigato, P.A., Zanonato, P.L., and Tamburini, S., Coordination ability of free or silica immobilized Schiff bases towards Hg(II), Cd(II) and Pb(II) ions, Inorganica Chimica Acta, 410, 29-38, (2014).
22. Sun, J., Sun, J., Mi, W., Xue, P., Zhao, J., Zhai, L., and Lu, R., Self-assembling and piezofluoro chromic properties of tertbutylcarbazole-based Schiff bases and the difluoroboron complex, Dyes and Pigments, 136, 633-640, (2017).
23. Yıldız, M., Demir, N., Ünver, H., and Sahiner, N., Synthesis, characterization, and application of a novel water-soluble polyethyleneimine-based Schiff base colorimetric chemosensor for metal cations and biological activity, Sensors and Actuators B: Chemical, 252, 55-61, (2017).
24. Chandra, R., Ghorai, A., and Patra, G. K. A simple benzildihydrazone derived colorimetric and fluorescent ‘on–off-on’ sensor for sequential detection of copper(II) and cyanide ions in aqueous solution, Sensors and Actuators B: Chemical, 255, 701–711, (2018).
25. Obali, A.Y., and Ucan, H.I., Novel dipodal Schiff base compounds: Synthesis, characterization and spectroscopic studies, Journal of Molecular Structure, 1081, 74-78, (2015).
26. Sarveswari, S., Beneto, A.J., and Siva, A., Colorimetric sensing of cyanide and flüoride ions by diaminomalenonitrile based Schiff bases, Sensors and Actuators B: Chemical, 245, 428-434, (2017).
27. Al Zoubi, W., Al Mohanna, N.D., Membrane sensors based on Schiff bases as chelating ionophores – A review, Spectrochimica Acta Part A, 132, 854-870, (2014).
28. Ghosh, S., Khan, M.A., Ganguly, A., Al Masum, A., Alam, Md. A., and Guchhait, N., Binding mode dependent signaling for the detection of Cu2+: An experimental and theoretical approach with practical applications, Spectrochimica Acta Part A, 190, 471–477, (2018).
29. Temel, E., Alaşalvar, C., Eserci, H., and Ağar, E., Experimental (X-ray, IR and UV–vis.) and DFT studies on cocrystallization of two tautomers of a novel Schiff base compound, Journal of Molecular Structure, 1128, 5-1215, (2017).
30. Govindasamy, L., Velmurugan, D., and Rajendran, T.M., An N...H-O intramolecular strong hydrogen bond in N-(2-aminophenyl)-naphthaldimine, Acta Crystallographica Section C, 55, 1368-1369 (1999).
31. Ohshima, A., Momotake, A., and Arai, T., Photochromism, thermochromism, and solvatochromism of naphthalene-based analogues of salicylideneaniline in solution, Journal of Photochemistry and Photobiology A: Chemist, 162, 473–479, (2004).
32. Bartyzel, A., and Kaczor, A.A., Synthesis, crystal structure, thermal, spectroscopic and theoretical studies of N3O2-donor Schiff base and its complex with CuII ions, Polyhedron, 139, 271–281, (2018).
33. Karakurt, T., Cukurovali, A., Subasi, N.T., Onaran, A., Ece, A., Eker, S., and Kani, İ., Experimental and theoretical studies on tautomeric structures of a newly synthesized 2,2'(hydrazine-1,2-diylidenebis(propan-1-yl-1-ylidene))diphenol, Chemical Physics Letters, 693, 132–145, (2018).
34. Rajaei, I., and Mirsattari, S.N., Spectroscopic characteristic (FT-IR, 1H, 13C NMR and UV-Vis) and theoretical calculations (MEP, DOS, HOMO-LUMO, PES, NBO analysis and keto–enol tautomerism) of new tetradentate N,N′-bis(4-hydroxysalicylidene)-1,4-phenylenediamine ligand as chelating agent for the synthesis of dinuclear Co(II), Ni(II), Cu(II) and Zn(II) complexes, Journal of Molecular Structure, (2018), in press
35. Jia, J.,Li, Y., and Gao, J., A series of novel ferrocenyl derivatives: Schiff bases-like push-pull systems with large third-order optical responses, Dyes and Pigments, 137, 342-351, (2017).
36. Cheng, L-X.,Tang, J-J., Luo, H., Jin, X-L., Dai, F., Yang, J., Qian, Y-P., Li, X-Z., andZhou, B., Antioxidant and antiproliferative activities of hydroxyl-substituted Schiff bases, Bioorganic and Medicinal Chemistry Letters, 20, 8, 2417-2420, (2010).
37. Güngör, Ö., and Gürkan, P., Synthesis and spectroscopic properties of novel asymmetric Schiff bases, Spectrochimica Acta Part A, 77, 304–311, (2010).
38. Güngör, Ö., and Gürkan, P., Potentiometric and antimicrobial studies on the asymmetric Schiff bases and their binuclear Ni(II) and Fe(III) complexes; synthesis, and characterization of the complexes, Arabian Journal of Chemistry, (2015), in press.
39. Özdemir, Ö. Novel symmetric diimine-Schiff bases and asymmetric triimine-Schiff bases as chemosensors for the detection of various metal ions, Journal of Molecular Structure, 1125, 260-271, (2016).
40. Özdemir Güngör, Ö., Intramolecular Proton Transfer Equilibrium in Salicylidene- and Naphthalene-based Tetraimine Schiff Bases, Gazi University Journal of Science, 30(1), 191-214, (2017).
41. Reyes-Arellano, A., Vega-Ramirez, L., Najera-Mundo, J.A., Salgado-Zamora, H., Molins, E., Peralta-Cruz, J., and Tamariz, J., An abnormal C–H••O bond directs intermolecular bonding arrangements in bisimines, Journal of Molecular Structure, 655, 141–148, (2003).
42. Sun, Y-X.,You, Z-L., and Zhu, H-L., N,N'-Bis(4-nitrobenzylidene)ethane-1,2-diamine, Acta Crystallographica Section E, E60, 1707-1708, (2004).
43. Özdemir (nee Güngör), Ö., Gürkan, P., Sarı, M., and Tunç, T., Synthesis of monosodium salts of N-(5-nitro-salicylidene)-D-amino acid Schiff bases and their iron(III) complexes: spectral and physical characterizations, antioxidant activities, Journal of Coordination Chemistry, 68, 2565-2585, (2015).
44. Barwiołek, M., Babinska, M., Kozakiewicz, A., Wojtczak, A., Kaczmarek-Kedziera, A., and Szłyk, E., New fluorescent [Ag(I)(Schiffbase)] complexes derived from 9-anthracenecarboxaldehyde and their application in thin layers deposition, Polyhedron, 134, 177–191, (2017).
45. Gonul, I., Kose, M., Ceyhan, G., and Serin, S., Methoxy group containing bidentate Schiff base ligands and their transition metal complexes: Synthesis, structural characterisation, photoluminescence, antioxidant capacity and superoxide dismutase activity studies, Inorganica Chimica Acta, 453, 522–530, (2016).
46. Ceylan, Ü., Çapan, A., Yalçın, Ş.P., Sönmez, M., and Ay, M., Vibrational spectroscopic and thermodynamical property studies, Fukui functions, HOMO-LUMO, NLO, NBO and crystal structure analysis of a new Schiff base bearing phenoxy-imine group, Journal of Molecular Structure, 1136, 222–230, (2017).
47. Orojloo, M., and Amani, S., Synthesis and studies of selective chemosensor for naked-eye detection of anions and cations based on a new Schiff-base derivative, Talanta, 159, 292-299, (2016).
48. Aydın, Z., and Keles, M., Highly selective Schiff base derivatives for colorimetric detection of Al3+, Turkish Journal of Chemistry, 41, 89-98, (2017).
49. Lee, S.Y., Kim, S.Y., Kim, J.A., and Kim, C., A dual chemosensor: Colorimetric detection of Co2+ and fluorometric detection of Zn2+, Journal of Luminescence, 179, 602-609, (2016).
50. Zhu, W.,Yang, L., Fang, M., Wu, Z., Zhang, Q., Yin, F., Huang, Q., and Li, C., New carbazole-based Schiff base: Colorimetric chemosensor for Fe3+ and fluorescent turn-on chemosensor for Fe3+and Cr3+, Journal of Luminescence, 158, 38-43, (2015).
51. Sathiyaraj, S.,Sampath, K., Butcher, R.J., Pallepogu, R., and Jayabalakrishnan, C., Designing, structural elucidation, comparison of DNA binding, cleavage, radical scavenging activity and anticancer activity of copper(I) complex with 5-dimethyl-2-phenyl-4-[(pyridin-2-ylmethylene)-amino]-1,2-dihydro-pyrazol-3-one Schiff base ligand, European Journal of Medicinal Chemistry, 64, 81-89, (2013).