IHJPAS. 36 (3) 2023 231 This work is licensed under a Creative Commons Attribution 4.0 International License *Corresponding Author :Noha.Ayad1205a@csw.uobaghdad.edu.iq Abstract Our recent work displays the successful preparation of Schiff_bases that carried out between hexane-2,5-dione and 2 moles of (Z)-3-hydrazineylideneindolin-2-one forming in Schiff-bases- (L), Which in turn allowed combining with each of the next metal ions: (M2+) = Ni, Mn, Zn, Cu and Co forming complexes_ in high stability. The formation of resulting Schiff_ bases (L) is detected spectrally using LC_Mss which gave approximately matching results with theoretical incomes, 1HNMR proves the founding of doublet signal of (2H) for 2NH, FTIR indicates the occurrence of two interfered imine bands and UV-VIS mean is also indecates the formation of ligand. On the other hand, complexes-based-Schiff were characterized using the same spectral means that relied Schiff-bases_(L). Those means gave satisfactory results and proved the distinguishable geometries that suggested. Finally, and according to the antibiotic feature of Schiff-bases and its metal ions we have also examined such character against (-Bacteria and +Bacteria) giving an acceptable inhibition efficiency. Key words: Hexadion ,Isatin-3-hydrazone, Schiff_bases complexes, biological activity . 1. Introduction Schiff bases are organic compounds originating from the condensation of a primary amine with an aldehyd e or a keton, to give imine_groups. Electronic and steric effects can be easily adjusted by the proper choice of the amine and substituted carbonyl compound, to provide Schiff bases with great structural variability [1, 2]. Schiff bases constitute an important class of ligands with wide application in coordination chemistry: these bases can serve as bis-, tris-, tetra-, penta- or polydentate ligands for transition and representative metals and ions.[3,4] The presence of other doi.org/10.30526/36.3.3071 Article history: Received 11 October 2022, Accepted 15 December 2022, Published in July 2023. Ibn Al-Haitham Journal for Pure and Applied Sciences Journal homepage: jih.uobaghdad.edu.iq Synthesis, Characterization and Biological Activity Study for Some New Metals Complexes with (3Z,3'E)-3,3'-(((2E,5E)-hexane-2,5-diylidene)bis(hydrazine-2,1- diylidene))bis(indolin-2-one) Nuha Ayad Abd AL_Qadir* Department of Chemistry, College of Education for Pure Sciences Ibn-Al-Haitham, University of Baghdad, Baghdad, Iraq. Noha.Ayad1205a@csw.uobaghdad.edu.iq Naser Dheyaa Shaalan Department of Chemistry, College of Education for Pure Sciences Ibn-Al-Haitham, University of Baghdad, Baghdad, Iraq. ndsh1972@gmail.com https://creativecommons.org/licenses/by/4.0/ mailto:Noha.Ayad1205a@csw.uobaghdad.edu.iq https://ejchem.journals.ekb.eg/?_action=article&kw=343574&_kw=Isatin-3-hydrazone mailto:Noha.Ayad1205a@csw.uobaghdad.edu.iq mailto:Noha.Ayad1205a@csw.uobaghdad.edu.iq mailto:ndsh1972@gmail.com mailto:ndsh1972@gmail.com IHJPAS. 36 (3) 2023 232 functional groups in the structure of the starting carbonyl and/or amine used to synthesize the Schiff base provides the imine with two or more different donor atoms,[5] predominantly nitrogen, oxygen and sulfur,[5, 6] but also phosphorus, selenium and tellurium, to chelate metals and ions.[7] As a result of their stability, facile preparation, structural variability and versatile coordinating capabilities, Schiff bases play a key role in coordination chemistry, and their coordination complexes have several applications.[8,9] All these advantages have led Schiff bases to be often called “Privileged Ligands.” [10, 11] In 1864, Hugo Schiff [12] was the first to synthesize Schiff bases. Although, this class of compounds has long been known, they are still extensively studied in diverse research fields. For example, numerous reviews have dealt with structures and reactions of Schiff base complexes [13] and their catalytic [14-16], biological, magnetic, electrochemical [17] and cancer treatment applications, which often depend on the Schiff base structure. 2. Materials and method 2.1 Methodology The starting materials including (MnCl2.4H2O ,CoCl2.6H2O ,NiCl2.6H2O, CuCl2.2H2O and ZnCl2) were commercially abundant in addition to the employed catalysts including (dimethyl sulfoxide, abs. ethanol. and diethyl-ether) that supplied from F-897ewluka, sigma aldrich. The employed FTIR apparatus operates in the range (200-4000) cm-1 Shimadzu-3800 model. Electronic spectral inform were accomplished depending on Shimadzu160-meter. LC/MSS incomes are also established by Mass100P_Shimadzu contribution. Pyrolysis diagnosis were carried out depending on perkin_Elmer_pyris Diamond D_S_C/TG. Proton-NMR was published using Bruker 400- MHz-meter and elemental micro analysis were done on a perkin_Elmer_automatical instruments model_240B. minerals were determined obeying a Shimadzu_(A-A)_680G AA_spectrometer. The Cl combination were estimated by conductivity measurements. Magnetic features were measured using balance magnetic susceptibility model MSR-MK 2.2 Organic ligand (Schiff-bases-(L)) and Metal complexes synthesis This ligand has been synthesis using the general strategy that used in Schiff base synthesis and carried out in round bottomed flask of 100 ml in volume. At which (1g, 2mol) of main substance (Z)-3-hydrazineylideneindolin-2-one is dissolved in 10 ml of EtOH. With continuous stirring and heating to perform the dissolution of the main substance. Then, (0.342g, 1mol) of hexane-2,5- dione is added onto the main substance solution. Finally, adding two drops of glacial acetic acid with reflux and continuous stirring about 4 hours resulting in olive precipitate as in Figure 1 below the (Schiff-bases_ (L)) synthesis. The former is filtered and dried in oven. H N N NH2H3C H N N N CH3 H2 C C H2 N H3C N NH O + 2 O CH3 O O hexane-2,5-dione sterring reflux-4-hour O L EtOH Figure 1. ligand synthesis IHJPAS. 36 (3) 2023 233 2.3 METAL complexes synthesis Cobalt complex of the obtained (Schiff-bases_ (L) has been prepared using the following approach: dissolving (0.08 g, 1 mol) of ligand_(L) in 10 ml of MeOH with continuous stirring and heating to perform the dissolution, Then adding (0.073 g, 0.001 mol) of Co-salt (CoCl2.6H2O) that dissolved in MeOH, then reflux and continuous stir ring for 4 hours. After completely reflux, mixture is filtered while its heat, dried, washed and adding a few drops of diethylether. Resulting in light orange precipitate with (215-219)⁰C. Other complexes of the following metal salts: NiCl2.6H2O (0.06 g, 1 mol), CuCl2.2H2O (0.08 g, 1 mol), MnCl2.4H2O (0.05g, 1 mol) and ZnCl2 (0.05g, 1 mol) , were prepared using the same approach that used in Co-complex synthesis Resulting in: light olive precipitate with (228-232)⁰C, brown precipitate with (215-220)⁰C, red precipitate with (275-279)⁰C and orange precipitate with (195-198)⁰C for each complex respectively. 3. Result and discussion 3.1 FT-IR studies FT-R spectrum of newly obtained ligand L in Figure 1. Displays a distinguishable absorption band at 1658 cm-1 contributes to azomethine formation, which can be strong evidence about ligand (L) synthesis. In addition ,the absent of asymmetrical absorption band of NH2-amino group. This can be strong indication that proves the formation of ligand through the interaction between carbonyl group of hexane-2,5-dione and amino group of isaten. It’s important to note the absent of C=O absorption band of hexane-2,5-dione which can also support the formation of ligand through this group. Other absorption bands were detected at (3155, 2900, 3356, 1683 and 1463) cm-1 that belonging to the stretching vibrational mode of the following functional groups: C-H aromatic, C- H aliphatic, N-H amine, C=O of amide and C=C of alkene respectively [18]. As demonstrated in Table 2 and figure 2 for Copper(II) complex [Cu(L)(Cl)(H2O)]Cl in Figure 2. Demonstrates many changes including shifting in stretching vibrational mode of C=N group because of the occurrence of coordination through N of both C=N groups, to be detected at 1618 cm-1. In addition, appearing new absorption bands at (580, 482 and 254) cm-1 attributed to the vibration of M-N, M-O and M- Cl respectively. Besides the bands of coordinated water molecule that observed at (3450, 1527 and 754) cm-1. Those new bands can strongly prove the formation of complex and the presence of H2O aqua inside coordination sphere [19, 20]. Other complexes in Figures 3, 4, 5 and 6 also display individually such modifications that happened in Copper complex as mentioned in Table 2. IHJPAS. 36 (3) 2023 234 Table 1. FT-IR spectral data of ligand (L) and its complexes Compound C-H Alph. C-H Atom C=N Imine N-H C=O amide C=C M-N M-O M-Cl H2O aqua C22H20N6O2 L 2900 (w-m) 3155 (s) 1658 (s) 3356 (m,b) 1683 1463 (m-w) -- -- -- -- [Cu(L)(Cl)(H2O)] 2985 (w-m) 3109 (w) 1618 (s) 3195 (m,b) 1691 s 1463 (m-s) 580 m 482 w- m 254 s 3450 1527 754 [Ni(L)Cl2(H2O)2] 2956 (w-m) 3161 (s) 1618 (s) 3215 (m,b) 1687 s 1465 (m-s) 501 m 445 w- m 256s 3359 1552 748 [Zn(L)Cl2] 2966 (w-m) 3064 (m) 1618 (s) 3201- 3218 (m,b) 1681 s 1463 (m-s) 541 m 497 w- m 223 S -- [Mn(L)Cl2(H2O)2] 2958 (w-m) 3050 (w) 1614 (s) 3163- 3215 (m,b) 1685 s 1465 (m-s) 520 m 499 w 297 s 3361 1552 748 [Co(L)Cl2(H2O)2] 2990 (w-m) 3050 (m) 1656 (s) 3161- 3217 (m,b) 1687 s 1465 (m-s) 520 w 499 w 239 S 3361 1554 748 s= strong, b= broad, m= moderate, w= weak Figure 1. FT-IR spectrum of ligand (L) Figure 2. FT-IR spectrum of Copper complex 500750100012501500175020002500300035004000 1/cm 30 40 50 60 70 80 90 100 110 %T 3 3 5 6 .1 4 3 1 5 5 .5 4 2 8 8 5 .5 1 2 8 0 2 .5 7 2 3 6 2 .8 0 1 9 4 0 .3 9 1 9 0 1 .8 1 1 7 9 3 .8 0 1 6 8 3 .8 6 1 6 5 8 .7 8 1 5 9 1 .2 7 1 5 5 0 .7 7 1 4 6 3 .9 7 1 4 0 2 .2 5 1 3 4 6 .3 1 1 2 4 6 .0 2 11 9 9 .7 2 11 5 7 .2 9 1 0 9 5 .5 7 1 0 1 2 .6 3 9 7 7 .9 1 8 7 7 .6 1 7 8 6 .9 6 7 4 6 .4 5 6 7 7 .0 1 6 3 4 .5 8 5 2 6 .5 7 4 9 9 .5 6 4 4 1 .7 0 IHJPAS. 36 (3) 2023 235 Figure 3. FT-IR spectrum of Nickle complex Figure 4. FT-IR spectrum of Zinc complex Figure 5. FT-IR spectrum of Manganese complex IHJPAS. 36 (3) 2023 236 Figure 6. FT-IR spectrum of Cobalt complex 3.2 UV-Vis studies Figure 7, demonstrates uv-vis spectrum of ligand (L), at which two π → π* transitions occurred at (236 nm, 42372.881cm-1) and (265 nm, 37735.849 cm-1). These transitions attributed to the presence of unsaturated bonds and aromatic rings in ligand’s structure. Other electronic transition that occurred in ultraviolet region is n →π* electronic transition at (316 nm, 31645.569 cm-1). This transition causes by the presence of heteroatoms in ligand’s structure such as (-N-) that contains nonbonding electrons [21]. Figure 8 Illustrates UV-Vis spectrum of Copper-L complex in diluted form at which ultraviolet transitions that referred to as π → π* and n → π* were shifted compared to the same transitions that observed in ligand’s spectrum to be observed at (265 nm, 37735.849 cm-1) and (304 nm, 32894.736 cm-1) for both transitions respectively. This modification causes by the occurrence of coordination with metal ion through both Schiff base groups. Moreover, single transition observed at visible region (978 nm, 10224.948 cm-1) in its concentrated form Figure 9, denoted as 2T2→ 2E the transition that found in metal itself. This transition and the magnetic moment [3.81B.M] can support (td) geometry of the complex [22]. By the same approach, we can apparently discuss the electronic transitions for the rest complexes that displayed in Figures 10, 11, 12 and 13 and Table 2, Figure 11. Illustrates UV-Vis spectrum of Cobalt-L complex at which ultraviolet transitions that referred to as 2 (π →π*) (202 nm, 49504.950 cm-1), (245 nm, 40816.326 cm-1) and n →π* (316 nm, 31645.569 cm-1). Were shifted compared to the same transitions that found in ligand’s spectrum. This modification causes by the occurrence of coordination with metal ion through both Schiff base groups. Moreover, the transitions that observed at visible region are as follows: 4A2g→ 4T2g (F) at (412 nm, 24271.844 cm -1), 4A2g→ 4T1g (F) (461 nm, 21691.973 cm -1) and 4A2g→ 4T1g (P) at (482 nm, 20746.887cm -1) those transitions are found in metal itself. Those transitions and the magnetic moment [2.79 B.M] can support (Oh) geometry of the complex [23]. IHJPAS. 36 (3) 2023 237 Table 2. UV-Vis spectral data of ligand (L) and its complexes Compound Abs. Ɛmax L.mol- 1.cm-1 λmax nm µeff B.M ύ cm-1 Transition C22H20N6O2 L 3.115 3.070 1.317 3115 3070 1317 236 265 316 -- 42372.881 37735.849 31645.569 *π→π *π→π *π→n [Cu(L)(Cl)(H2O)] 1.213 0.663 0.002 1213 663 2.00 265 304 978 1.62 37735.849 32894.736 10224.948 *π→π π→n E2→2T 2 [Zn(L)Cl2] 4.000 3.950 4.000 1333 321 488 299 310 406 diamagnetic 40322.581 37037.037 30303.030 *π→π π→n C.T(M→L) [Co(L)Cl2(H2O)2] 2.857 0.282 4.000 4.000 4.000 4.000 2857 282 4000 4000 4000 4000 202 245 316 412 461 482 3.12 49504.950 40816.326 31645.569 24271.844 21691.973 20746.887 π → π* n → π* n → π*+ (C.T ) 4A2g→ 4T2g (F) 4A2g→ 4T1g (F) (P) g1T 4g→2A 4 [Mn(L)Cl2(H2O)2] 0.952 4.000 4.000 0.004 952 4000 4000 4.000 212 352 401 908 2.79 47169.811 28409.090 24937.655 11013.215 π → π* n → π* 6A1→ 4T1G 6A1g→ 4A1g+ 4EG [Ni(L)Cl2(H2O)2] 1.997 1.660 0.002 1997 1660 2.000 303 325 978 3.81 33003.300 30769.230 10224.948 π → π* n → π* 3T1F→ 3T2F Figure 7. UV-Vis spectrum of ligand Figure 8. UV-Vis spectrum of dill. Copper complex nm. 190.00 400.00 600.00 800.00 1100.00 Ab s. 4.000 3.000 2.000 1.000 0.000 1 23 4 5 67 nm. 190.00 400.00 600.00 800.00 1100.00 Abs . 1.500 1.000 0.500 0.000 1 2 3 4 IHJPAS. 36 (3) 2023 238 Figure 9. UV-Vis spectrum of conc. Copper complex Figure 10. UV-Vis spectrum of Zinc complex IHJPAS. 36 (3) 2023 239 Figure 11. UV-Vis spectrum of Cobalt complex Figure 12. UV-Vis spectrum of Manganese complex Figure 13. UV-Vis spectrum of Nickel complex nm. 190.00 400.00 600.00 800.00 1100.00 Ab s. 3.000 2.000 1.000 0.000 1 2 3 4 5 IHJPAS. 36 (3) 2023 240 3.3 Nuclear magnetic resonance spectrum of ligand 13C-NMR & 1H-NMR 1H-NMR spectrum in Figure 14 and Table 4 Demonstrates the next signals: two singlet signals at δ (2.5 and 3.5) ppm belongs to (2H) 2CH2 and (3H) 2CH3 , Doublet signal at δ (9.55-9.60) ppm belongs to (2H) 2NH group, multiplet signal at (6.8-7.4) ppm belongs (8H) 2Ar- H. This measurement was carried out using DMSO-6 as solvent, which in turn gave a signal at (2.31-2.64). TMS is used as reference [24, 25]. 13C-NMR spectrum in Figure 15 demonstrates the next signals : (100.622 MHz, DMSO-d6) that gave a signal at 40 δ ppm: (110-130) δ ppm belong to (C3-C7) of aromatic ring, 140 δ ppm belong to (C8 and C9), 160 δ ppm belongs to C10 and C11 [26]. Table 4. 1H-NMR spectral data of ligand (L) Figure 14. 1H-NMR spectrum of ligand (L) Figure 15. 13C-NMR spectrum of ligand (L) Compound 1H-NMR δ ppm C22H20N6O2 L Singlet (2H) 2CH2 2.5 Singlet (3H) 2CH3 3.5 Doublet (2H) 2NH 9.55-9.60 Multiplet (8H) 2Ar- H 6.8-7.4 IHJPAS. 36 (3) 2023 241 3.4 Mass Spectrum of Ligand In coordination chemistry, mass spectroscopy is widely used as a potent structural characterization tool. Mass spectra fragmentation analogues for free Schiff base ligand [C22H20N6O2] were acceptable compared to its structure in scheme1. Characterized the mass spectrum an intense peak at 401.287 m/z that approximately matching its calculated molecular weight 400.44 m/z [27]. Figure 16. LC-MSS spectrum of ligand (L) 3.5 Bioactivity evaluation of the Ligand (L) and its complexes Two types of bacteria were tested, (-Bacteria (Escherichia_coli) and +Bacteria (Staphellococcus_aureus)). The effect of the synthesized Schiff-species and its complexes on the mentioned bacteria were tested and compared in 0.001M (DMSO-solvent) as control and the results are recorded in Table 4. These results indicate that, the Schiff-species (ligand L) and Nickle complex has negative inhibitory action toward Staphylococcus_aureus bacteria besides, whereas the rest compounds were effective toward both types of bacteria [28]. All the details are demonstrated in Figure 17. Figure 17. Biological evaluation-incomes 0 5 10 15 20 25 30 (HL) Zn-L Mn-L Cu-L Ni-L Co-L The Bioactivity Chart E-coli Staphcusyloco IHJPAS. 36 (3) 2023 242 Table 4. Bioactivity results of Schiff-species-(L) and its complexes Compound Escherichia_coli Staphylococcus_aureus C22H20N6O2 16mm 10mm [Zn(L)Cl2 14mm 24mm [Mn(L)Cl2(H2O)2] 14mm 24mm [Cu(L)(Cl)(H2O)] 26mm 27mm [Ni(L)Cl2(H2O)2] 16mm 8mm [Co(L)Cl2(H2O)2] 20mm 24mm 4. Conclusion Recently synthesized Schiff-bases_(L) (3Z,3'E)-3,3'-(((2E,5E)-hexane-2,5-diylidene) bis(hydrazine-2,1-diylidene)) bis(indolin-2-one) was successfully obtained using common condensation combination between hexane-2,5-dione and 2 moles of (Z)-3- hydrazineylideneindolin-2-one, Which forms massive stability Schiff-bases-(L)-complexes in specific conditions of preparation. Spectrally and using FTIR spectrometry this ligand and coordinates with employed metal ions (M2+) = (Ni, Mn, Zn, Cu and Co) through both azomethine functional groups. The information of such apparatus indicating the formation of M-N and M-O belongs to aquatic water molecule that attaches to metal ions except for (M2+) = Zn. 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