IHJPAS. 36(1)2023 208 This work is licensed under a Creative Commons Attribution 4.0 International License Synthesis, Spectroscopic, and Biological Activity Study for New Complexes of Some Metal Ions with Schiff Bases Derived From 2-Hydroxy Naphthaldehyde with 2-amine benzhydrazide Abstract This study describes the preparation of tetradentate Schiff base derived from the condensation of 2-Hydroxy naphthaldehyde with 2-amine benzhydrazide and the synthesis of new complexes series with a good yield.The prepared ligand was characterized using a microanalysis technique, UV-visible, FT-IR, nuclear magnetic resonance 1H-NMR, mass spectrometry, thermal gravimetric analysis TGA, and the addition of conductivity measurement and magnetic moment of complexes. The invitro antimicrobial activity of the prepared compounds was tested against Gram-negative Klebsiella pneumonia, Gram-positive Staphylococcus aureu, and Candida albicans by the agar well diffusion method. The spectroscopy and measurement studies showed that the ligand coordinated with the metal ion as a tetradentate ligand via oxygen and nitrogen, forming an octahedral geometry around it. The ligand and its complexes positively affect the studied microorganisms' Gram-positive and Gram-negative strains and fungi. Keywords: 2-Hydroxy naphthaldehyde, 2-amine benzhydrazide, Biological activity, Schiff base complexes. 1.Introduction The chemistry of Schiff bases and their mineral complexes has become an area of interest for researchers because of their significant impact on human life and the environment. A general method for the synthesis of Schiff bases is the product of the condensation of aldehydes or ketones with primary amines and was first reported by the German scientist, Hokoschiff (1). doi.org/10.30526/36.1.2978 Article history: Received 14 Augest 2022, Accepted 15 September 2022, Published in January 2023. Ibn Al-Haitham Journal for Pure and Applied Sciences Journal homepage: jih.uobaghdad.edu.iq Bushra Mohan Department of Chemstry , College of Science for Women, University of Baghdad,Baghdad, Iraq. boshra.mohan1205a@csw.uobaghdad.edu.iq Naser Shaalan Department of Chemstry , College of Science for Women, University of Baghdad,Baghdad, Iraq. naserds_chem@csw.uobaghdad.edu.iq https://creativecommons.org/licenses/by/4.0/ mailto:boshra.mohan1205a@csw.uobaghdad.edu.iq mailto:naserds_chem@csw.uobaghdad.edu.iq IHJPAS. 36(1)2023 209 Schiff bases also described as an important mediator in many reactions, especially the formation of important porphyrins in the human body, the interaction that occurs between pyridoxal (vitamin B6) and amines and the resulting compound is (N-pyridoxylic) Schiff bases (2). This vital importance of Schiff's rules has made them enter many areas of applied scientific research. Among the areas in the field of pharmaceutical chemistry, pharmaceutical industries, including antioxidants (3), antibacterials, antifungals, anticarcinogens (4,5), antivirals, and anti- tuberculosis (6,7) antibacterials, It has also entered the field of the industry including the manufacture of dyes (8) and polymer stabilizers and sensors (9). It should be noted that inorganic coordination chemistry has made a quantum leap through the synthesis of various coordination compounds, especially stable, essential, and biologically active chelating compounds (10, 11), including heterocyclic compounds (12). They have also attracted researchers' interest in their catalytic and biological applications and are not limited to Schiff bases. The preparation of mineral complexes from Schiff bases with metal ions is the most important achievement that made it enter the industrial and medical fields (13), especially the pharmaceutical industry and the manufacture of insecticides, fungicides, and pesticides. Herbs and antioxidants. Which protect the living body from damage caused by harmful molecules called free radicals. The body produces cells in response to free radicals (14). 2- hydroxynaphthaldehyde derivatives have topped Schiff's rules for their importance, flexibility, and diversity of effectiveness of their compounds in all areas. In this study, we present Schiff base ligand and metal complexes that were prepared from transition metal ions as well as zinc ion. Most of these compounds have biological activity that showed good results on gram-negative and gram-positive bacteria and promising efficacy in inhibiting the activity of fungi. 2. Materials and methods 2.1 Materials All reagents and chemicals used in this study were in the analytical grade and purchased from (Sigma-Aldrich). 2-Hydroxy naphthaldehyde 99%, 2-amine benzhydrazide 97%, MnCl2.2H2O 99%, NiCl2.6H2O 99%, CuCl2.2H2O 99%, CoCl2.6H2O 99%, and ZnCl2 98% were provided from BDH and used as received. The FT-IR spectra of the ligand and its complexes were recorded within the range (200- 4000) cm- 1 using a device of type (Shimadzu FTIR-Spectrometer) and using disk (KBr) for ligand and (CsI) for complexes at the University of Baghdad/ College of Science / Department of Chemistry. Measuring magnetic sensitivity by John Mathey device - England at Al-Nahrain University \ chemistry department The 1H-NMR spectra of the as-prepared bond were recorded using a Bruker 300MHz AVANCE spectrometer with DMSO as solvent at room temperature (Tehran). A GC-Mass-Agilent 5975c instrument recorded the mass spectra of the prepared compounds for the ligand and the compounds studied using the (Elementer Vari) instrument at Shahid Beheshti University in Tehran / Islamic Republic of Iran. IHJPAS. 36(1)2023 210 Ultraviolet Spectrophotometer A 160. The prepared solutions were at a concentration of (1×10-3 molar) in dimethylformamide (DMF) solvent. The melting point of the prepared ligand and its complexes were measured using an (SMP10) device from the English company Stuart in the temperature range of 300 °C. The molar conductivity was measured with a WTW meter, and the UV-visible spectra in the range (190.00-1100) nm were measured using a Shimadzu UV-Vis device. 3. Synthesis 3.1 Synthesis of the (L) ligand A solution of 2-hydroxy-1-naphtaldehyde (0.782 gm,0.0045 mol) in 15 ml ethanol was mixed with (0.68gm, 0.0045mole) 2-amine benzhydrazide in 10 ml of ethanol and three drops of glacial acetic acid were allowed to react in a 50 ml round bottom flask. The mixture was added under stirring and refluxed for 5 hrs. A yellow precipitate formed was collected by filtration, washed, and recrystallized with a mixture of hot methanol/ethanol (50:50) and then dried at 50 C0. The yield of the prepared ligand was 55%, as shown in Scheme 1. Scheme 1.Synthesis L ligand 3.2. Preparation of Metal Complexes L ligand complexes New complexes were synthesized by mixing 10ml methanol of the metal salt (0.0018mole) (where M2+= Mn2+, Co2+, Ni2+, Cu2+, and Zn2+) with of the ligand (0.0018mole) (1:1) (M:L) as dissolved in 10ml of methanol. The solution was stirred under heating at 50 °C for 2 hrs until the precipitate was formed. The colored complexes were separated by filtration, washed with methanol and ether, and left to dry at 80C. IHJPAS. 36(1)2023 211 Table 1. Physical data and elemental analysis of ligand and its metal complexes 4. Results and Discussion 4.1-FT-IR Spectra 4.1.1-FT-IR Spectra of L-Ligand The table below presents the infrared frequency bands of the Schiff base and its metal complexes. The potential binding sites through the donors are nitrogen, isomethane ( (-C = N) group, a hydroxyl group (-OH), aromatic amine group-NH2 and carbonyl group C=O. The FT-IR spectrum showed the bond synthesis method (L) in (Scheme 1). Also, the data of the ligand FT-IR spectra of the ligand showed the disappearance of (C = O) bundles of the aldehyde in the region (1683) cm-1 and the amino group (-NH2) in the region 3288-3323 cm -1 and the appearance of new peaks which are the link bundles of the imine group of the prepared ligand that was in (1546) cm- 1The infrared spectrum of L-free ligands showed weak broad absorption bands at 3440.77 cm-1, 1093 cm-1, and 2939 cm-1 due to the stretching vibration of (OH), (C-O-H) and (=C-H) aldehyde (imine) respectively for L ligand. C o m p o u n d m o le c u la r fo rm u la c o lo r M .w t g \m o l Y ie ld ( % ) C % H % N % M o la r C o n d u c ta n e Ω -1 C m 2 M o l- 1 a t 2 6 C ◦ M e lt in g p o in t (0 C ) L C18H15N3O2 yellow 305.3 5 85% 70.21 (70.81) 4.626 (4.95) 13.62 (13.76) _ 190- 194 L+Mn C18H16N3O3MnCl 2 dark goldenro d 448 68.16 49.72 (48.42) 3.83 (3.60) 9.38 ( 10.71) 7.9 >300 L+Co C18H16N3O3CoCl2 smith green 452 81.7 48.41 ( 47.81) 3.44 ( 3.57) 9.50 (9.29) 12.9 Dec. L+Ni C18H16N3O3NiCl2 pumpkin 452 91.9 47.67 (47.84) 3.936 (3.57) 8.552 (9.30) 67.26 >300 L+Cu C18H16N3O3CuCl2 olive 457 80.21 57.77 (58.77) 3.92 ( 3.84) 10.54 (11.42) 11.1 Dec. L+Zn C18H16N3O3Zn Cl2 yellow 459 79.17 59.31 (58.48) 3.806 (3.82) 12.14 11.37 24..2 >300 IHJPAS. 36(1)2023 212 Figure 1. IR for Ligand L 4.1.2- FT-IR spectrum of the L . complexes The comparison of the IR spectrum data of the complexes with the Free Schiff base indicates that the range of the imine group (HC = N) in the L complexes in L complexes has been shifted from (1608) cm-1 to lower frequencies in all five complexes, indicating the binding of the nitrogen atom in the group Coordination of nitrogen with a metal ion is expected to reduce the electronic density to lower frequencies in all five complexes, as the new bands of the isomethene group appeared in the region from ( 1541–1546.91) cm−1 Additionally, new weak bonds appear at ʋ (550-200) cm-1 and are related to ʋ (M-N), ʋ(M-O), ʋ (M-Cl) guide to coordination and formation of Schiff complexes. The new bands appeared in the region (366-424), cm-1 indicating the bonding of the nitrogen of the isomethine group with the metal, indicating the association of the nitrogen atom with the imine group (C = N) in coordination with the mineral (16).As shown in the tables, the disappearance of broad bands in the range (3350- 3440) cm-1 belonging to phenol hydroxyl (O) complexes is evidence of their chelation by a phenolic oxygen atom (17). It appeared in the range (503-592) cm-1. A new beam due to the vibrations of the stretching group (M-O) showed the stretching group (M-N) of the as-prepared complexes in the confined region between (366-464) cm-1, confirming the metallicity. Cross- linking (N) atom Azomethine binding causes a shift in the ν group (CH = N). The absorption peak of the Schiff ligand is about 3440 cm-1 due to the phenolic hydroxyl group of the Schiff base ligand, and this absorption peak disappears during the process of binding with metal using metal ions. This confirms coordination through phenol (-OH) and the central metal ion (18). IHJPAS. 36(1)2023 213 Table 3.FT-IR data of Ligand and its metal complexes (cm-1) comp. V(M- OH2) (OH) V(C=N) V(C=C) v(C-H) V(N-H) V( M- Cl) V( M-O) V(M-N) L 3440.77 1608 1541.02 2999 3600 ---- ----- ----- Mn+L 3481.51 1546.91 1517.98 2871.51 37481 270 - 300 - 333 (424) 514.99 Co+L 3680 1546 1514 2883.66 3745.75 270 - 333.69 (464) 514.99 Ni+L 3369.41 1541 1541 2954 3585.42 235.30 - 258.44 (418) 555.14 Cu+L 3481.51 1546 1514 2883.58 3746.76 266.18 - 305.75 (550) 374.19(s) Zn+L 3452.58 1546.91 1514.12 -2877.79 2819.93 3745.75 262 - 270 (424.34) 503.42- 578.64 Figure 2. Zn+LComple Figure 3.Cu+ Lcomple IHJPAS. 36(1)2023 214 Figure 3.Co +L complex Figure 4. Mn +L complex Figure 5.Ni+L complex 4.2-1HNMR Spectrum The Schiff base ligands and its complexes were investigated by Burker 300 MHz and using a DMSO solvent. The examined samples showed a set of traceable signals as follows: Proton analysis of the linker showed a set of signs, the first sign in the shift (δ = 2.49, 2.50, 2.51 ppm) was attributed to the solvent DMSO and the next sign in the shift was two signs (δ = 3.32 ppm, 3.33 ppm,) for the presence of impurities in the compounds, The tag (δ = 9.46 ppm, H+: NH) is believed to be a proton of the NH amide group. A mark appeared after the displacement (δ = 8.21 ppm, 2H+: NH2) that is believed to be a proton of the NH2 amine group attached to the benzene ring. a mark after the displacement (δ = 8.18 ppm, H+) attributed to the proton of the carbon of the isomethine group. Thet protons of two naphthaldehyde rings showed signs of displacement (δ = 7.24-7.91 ppm, 10H+). Finally, in displacement (δ =12.91 ppm, H+ : OH) a sign appeared that could be attributed to the proton of the hydroxyl group. IHJPAS. 36(1)2023 215 Figure 6. 1H-NMR Spectrum of complexes Figure 7.1H-NMR L+Ni Figure 8.1H-NMR L+Zn 4.3-Mass Spectra The molecular weight of Schiff base L was determined using GC-Mass-Agilent 5975c technology. The mass spectra gave the compound's molecular weight identical to what was calculated theoretically (m/e = 305) corresponding to (C18H15N3O2) M +, which is equal to 100% of the weight of the compound. The best peak of the ion appeared at m/e = 120 due to (C7H6NO) M +, equal to 39%. The best peak of the ion m/e = 104.1 is due to (C7H5CO) M +, which is equivalent to 34%. Then the peak of the ion m/e = 92 returns to (C6H4O) M +, which is equal to 30%, then the absorption peak m/e = 77 returns to (C5HO) M +, which is equal to 25%. Then, the maximum absorption m/e = 65 returns to (C4HO) M +. It is equal to 21% in the end. The absorption peak of m/e = 51 is due to (C3O) M +, which equals 16. 7%. IHJPAS. 36(1)2023 216 Figure 9. GC-Mass of Ligand L 4.5-UV Spectra The electronic absorption spectra of Schiff bases and their complexes are shown in the table below. It was applied with dimethylformamide (DMF) solvent, and sample solutions were prepared at a concentration of 0.001 M. Three bands appeared in the ligand (Schiff base) spectrum in the regions (361,320,224) nm indicating (n → π*), (π → π*) azomethine and hydroxy oxide group transitions, and C = C aromatic bond. The electronic spectra of the Co(II) complex showed absorption bands at (483–421) nm, the 4T1g → 4T1g (p) transitions. The occurrence of these transitions indicates the formation of an octahedron around the Co (II) ion. The magnetic measurements of the cobalt compound also showed a value (1.78 BM) located within the octahedral domain. The nickel complexes showed three absorption bands in the regions (944-499-443) nm, indicating that transitions occurred, respectively, 3A2g (F) → 3T2g (F), 3A2g (F) → 3T1g (F), 3A2g (F) → 3T1g (P). This corresponds to the octahedral composition and the magnetic moment of the nickel binary complex was (1.96 BM), and this corresponds to nickel octahedral complexes subjected to antiferromagnetic interference. As for the copper complex, three absorption bands appeared in the absorption regions (649 - 247) nm. The first beam is stimulated at the transitions 2B1g → 2A1g, 2B1g → 2Eg, located within the Hexagonal coordination bands, specifically octahedral. The Mn complex gave a magnetic moment value (1.67 BM) which is less than the spin of one electron. This is due to antimagnetic interference. The zinc compound is non-magnetic and does not give transitions in the visible region because its outer shell is saturated with d10. It is classified among octahedral complexes depending on the infrared spectrum. Table 4. UV-VIS data and magnetic moment value for Ligand and its metal complexes. IHJPAS. 36(1)2023 217 Table 3. UV-VIS data& magnetic moment value of Ligand and its metal complexes NO. Compound color Absorption Bands (nm) Assigned transition µeff (BM) Suggested Structure 1- L Ligand (C18H16N3O2) yellow 361 224 n→π* → C=N π→π*, →aromatic ring ----- ------ 2- [CoLCl2]H2O smith green 483 421 337 4T1g→4T1g(p) Charge transfer 1.78 Oct. 3- [NiLCl2]H2O pumpkin 944 499 443 3A2g (F → 3T2g(F) 3A2g (F) → 3T1g(F) 3A2g (F) → 3T1g(P) 1.96 Oct. 4- [CuLCl2]H2O olive 649 440 247 2B1g → 2A1g 2B1g → 2Eg Charge transfer 1.84 Oct. 5- [MnL Cl2]H2O dark goldenrod 446 423 Charge transfer 1.67 Oct. 6- [ZnLCl2]H2O yellow 534 363 216 Ligand spctrum Charge transfer Dia Oct. Figure10.L Ligand UV-Spectra Figure 11. UV-Spectra of complexes IHJPAS. 36(1)2023 218 4.6-Thermogravimetric analysis Thermogravimetric analysis: The reaction was carried out At (0.0 - 900) °C at about ten (10) degrees per minute. Thermal weight loss (TGA) and differential thermogravimetric analysis (DTG) in an atmosphere of air showed that (TGA), the curve of the ligand and its metal compounds was correct going through several stages of weight loss. It started with the exit of water and volatiles. The weight loss of the nickel (II) compound was analyzed in the following stages. The first stage got at (48-95) degrees Celsius, and it seemed to lose water outside the consistency ball. The percentage of weight lost was calculated (3.9%) and compared with that found (4%). In the second phase of weight loss, it is estimated that it started at (335-510) degrees Celsius, and the bulk of the weight has been lost. It was calculated as 63.7%, and it was actually found to be 63%. In the last stage, metal oxide residue (NiO) was found, and its calculated percentage equals (17%), and it was actually found equal to (18%). The zinc (II) compound was analyzed in stages: In the first stage: a period ranging (from 75-150) °C, the water loss outside the consistency ball with chlorine was consistent with the metal The loss of water outside the consistency ball with chlorine was consistent with the mineral. The weight loss was calculated and was equal to 18% of the complex weight, while it was found equal to (19.4%).In the second stage of decomposition, it was estimated that it occurred in the period (330-410) C◦, and it was found that the lost weight of the compound was 20%. The calculated percentage coincided with the real one. The third stage of decomposition was estimated to occur in the period (410-640) C◦. The weight lost was calculated at 43.3%, while it was actually found equal to 46%.The increase in weight was explained by interactions with the atmosphere (air), such as oxidation, because the atmosphere in which the reaction occurred was not inert. Finally, it was found that the metal oxide remained, and it was calculated at 17.3%. Its actual presence was 16%. The table below shows the stages of pyrolysis. Table 5. Summarizes the pyrolysis processes of compounds Sample (step) Tem .range ºC TG Weight mass loss Calc% found% Reaction NOTE L ( I) 70-98 10 10.3 N2H L ( II) 200-240 34.05 33.7 C7H4O L III 240-590 39.299 40 C7H6NO LIV 590-800 9.169 9.1 C2H4 Final residual 7.5 6.9 C2 L+Ni 48-95 3.9 4 H2O 15.4 15 Cl2 335-510 63.7 63 C18H14N3O Final residual 17 18 NiO L+Zn 75-150 19.4 18 H2O+ Cl2 330-410 20 20 C6H6N 410-640 43.3 46 C12H8N2O The increase in weight explains that the missing part was subjected to an oxidation process Final residual 17.3 16 ZnO IHJPAS. 36(1)2023 219 Figure 12. weight loss chart in Lligand Figure 13. weight loss chart in Ni compiexes IHJPAS. 36(1)2023 220 Figure 14. weight loss chart in Zn compiexes 4.7-Biological Activity The biological activity data are shown in Table 6 and Figure 13 and 14. Data for the Schiff base ligand (L) and its metal complexes are presented in Table 6 below. They were tested and evaluated for their antibacterial and antifungal activity by etch-diffusion technique. The solution of the compounds was prepared in a DMF solvent at a concentration of 0.01 M (mol). Two types of pathogenic bacteria were selected under aerobic conditions at (37°C) for 24 hours, Gram- negative Klebsiella pneumonia, Gram-positive Staphylococcus aureu, and Candida albicans. Bacteria and fungi were preserved in nutrients, and the test showed positive results for Schiff's base and L mineral complexes, where the copper complex was No. 2. Zinc was the most active against gram-positive bacteria, while cobalt complexes No. 7 and copper No. 4 were the most active against gram-negative bacteria. Copper was most effective on Candida albicans, followed by nickel. IHJPAS. 36(1)2023 221 Staphylococcus aureu Klebsiella pneumonia Candida albicans Figure 15. Biological acitivity of L ligand and its compiexes Table 6. The antibacterial activity of the prepared compounds MIC minimum inhibitory concentration(10-2 M) Ofoxacina (C18H20FN3O4) Fluconazoleb (C13H12F2N6 O) N O . compounds S ta p h y lo c o c c u s a u re u s K le b sie lla p n e u m o n ia e N O . compounds C a n d id a a lb ic a n s 1 Solvent DMF ne g a tiv e n e g a tiv e 1 Solvent DMF 20 2 Ligand A2 15 16 2 Ligand A2 22 4 O2 ]H2[Mn(A2)Cl 15 16 6 O2]H2[Mn(A2)Cl 23 7 O2]H2[Co(A2)Cl 16 23 3 O2]H2[Co(A2)Cl 22 5 O2]H2[Ni(A2)Cl 17 17 7 O2]H2[Ni(A2)Cl 24 4 O2]H2[Cu(A2)Cl 23 23 4 O2]H2[Cu(A2)Cl 26 3 O2]H2[Zn(A2)Cl 20 20 5 O2]H2[Zn(A2)Cl 22 standard a4.32 a4.32 b20.41 https://ar.wikipedia.org/wiki/Carbon https://ar.wikipedia.org/wiki/Hydrogen https://ar.wikipedia.org/wiki/Fluorine https://ar.wikipedia.org/wiki/Fluorine https://ar.wikipedia.org/wiki/Oxygen https://ar.wikipedia.org/wiki/Carbon https://ar.wikipedia.org/wiki/Hydrogen https://ar.wikipedia.org/wiki/Fluorine https://ar.wikipedia.org/wiki/Nitrogen IHJPAS. 36(1)2023 222 Figure 16. Antibacterial activity of ligand and their complexes 5.Conclusion According to the previous study, the ligand was prepared by the traditional reverse reaction method. It was found that it combined with metal ions in a chelating manner.This was demonstrated by the above analyses, including infrared spectrometry that showed bonds, ultraviolet analysis, mass spectrometry analysis, gravitational and thermal analyses, etc. The study of the biological activity of the ligand and the complexes also proved that all the prepared compounds can be described as biologically active against microbes. Figure 17. Suggested structure for complexes ( Mn,Co,Ni,Cu, Zn) References 1.El-Boraey, H.A.; El-Gammal, O.A.; Abdel Sattar, N.G. Impact of Gamma-Ray Irradiation on Some Aryl-Amide-Bridged Schiff-Base Complexes: Spectral, TGA, XRD, and Antioxidant Properties. J. Radioanal. Nucl. Chem. 2020, 323, 241–252. 2.El‐Sonbati1,A.Z., et al. 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