SYNTHESIS AND CHARACTERIZATION OF NOVAL SCHIFF BASE COMPLEXES OF MN(II), CO(II), NI(II), CU(II), ZN(II), PD(II), PT(II) METAL IONS FOR MICROBIAL ACTIVITIES AND THEIR NANOPARTICLES
HTML Full TextSYNTHESIS AND CHARACTERIZATION OF NOVAL SCHIFF BASE COMPLEXES OF MN(II), CO(II), NI(II), CU(II), ZN(II), PD(II), PT(II) METAL IONS FOR MICROBIAL ACTIVITIES AND THEIR NANOPARTICLES
Manisha G. Kapade, Pooja P. Batawale, Uttara M. Dalvi and Manohar V. Lokhande *
Department of Chemistry, Sathaye College (Autonomous), Vile Parle East, Mumbai, Maharashtra, India.
ABSTRACT: New Schiff base metal ion complexes are synthesized and characterized by Mass, TGA, DTA, FTIR, UV-Visible, Conductivity, Magnetic properties, SEM, TEM EDX, and Elemental Analysis. The complexes have the general formula [ML2.H2O], where L=3-{(Z)-[(2-aminophenyl) methylidene] amino}-4-chlorobenzoic acid, and M= Mn (II), Co (II), Ni (II), Cu(II), Zn (II), Pt(II), and Pd(II). The Schiff base's imino, amine, and carboxylic groups form a bond, the bands observed in the FTIR of the complexes. UV-Visible spectra of the complexes show that they are colour except for Zn (II) complexes. The parameters like the Nephelauxetic effect, covalence parameter b1/2, and co-valence (δ%) are calculated. The complexes are covalent. The central metal ions have eight coordination numbers, and the ligand behaves as bidentate. According to SEM TEM, EDX, and elemental analysis of the complexes, the size of prepared nanoparticles is 16-84 nm. The mass spectra of the ligand and complexes match the theoretically estimated values of Schiff bases and complexes. According to TGA and DTA complexes decompose when temperature rises, and two coordinated water molecules are present in the coordination sphere. The gram-positive and gram-negative bacteria have been used to screen Ligand and their complexes show an inhibitory effect.
Keywords: FTIR, Mass-spectra, UV-Visible, TGA/DTA, SEM, TEM, and EDX
INTRODUCTION: Schiff bases were easily made by condensing real carbonyl groups through primary amines, and they fit into the same appealing class of chemical compounds1-3. By adjusting the aldehydes/ketones and primary amines, it is simple to fine-tune the physicochemical features of Schiff bases and their transition metal complexes 4-6.
Because Schiff bases are stable in a variety of settings, one of their key characteristics is their capacity to build the coordination capability of transition metal ions 7-8. In metal complexes generated from Schiff bases, the coordination sphere's surrounding environment may be modified by substituting several species that are suited for forming the preferred steric and electrical characteristics 9.
Due to their adaptability, versatility, and wide range of applications 10-11, Schiff bases chemistry is becoming a more significant and comprehensive study area. They can bind a variety of metal ions to create complexes thanks to their multifunctional structures and capabilities 12-13. Imino or diamino groups of Schiff bases with OH groups in orthogonal positions to amino groups are given more attention 14-15. Their metal complexes exhibit potent antibacterial and antifungal properties 16-17, antioxidant properties 18, anticancer properties 19, anti-inflammatory properties 20, and catalytic properties 21. In this research paper, we synthesized Schiff bases and their transitional metal ion complexes.
MATERIALS AND METHODS: Without additional and further purification, AR, LR-grade chemicals, and reagents were used. Mark Chemicals supplied 3-amino-4-chlorobenzoic acid, Lobo Chemicals provided 2-amino benzaldehyde, and SD Fine Chemicals supplied metal chlorides and nitrates
Synthesis of Schiff Base: In a 25 cm3 flask, 1.71g of 3-amino-4-chlorobenzoic acid and 1.21g of 2-amino benzaldehyde were individually dissolved in 100% alcohol. The two solutions were then combined in a 250 cm3 round-bottom flask. Following the mixing of these solutions, a water condenser was used to reflux them for three hours at 120°C. During this time, two to three drops of 1M acetic acid were added. The final solution was allowed to cool to ambient temperature after three hours. After obtaining the solid precipitate, it was filtered with Whatman filter paper-41 and dried in a hot air oven at 60 °C. The product has a 93% yield.
Synthesis of Metal Ion Complexes: Double distilled alcohol was used to create the [3-[(Z)-(2-aminophenyl) methylidene]- amino}-4-chloro benzoic acid (0.02M) solution, and double distilled water was used to prepare the metal chloride solutions [M= Mn (II), Co(II), Ni(II), Cu(II), Zn (II), Pt(II), and Pd(II)]. Using a water condenser, the equi-molar concentration solutions of Schiff base (0.02M) and metal chloride (0.02M) were refluxed for 2.00–2.30 hours on a hot plate while being continuously stirred by a magnet. Two to three drops of alcoholic ammonia (1:1) were applied dropwise during refluxing, and different metal ions aside from zinc (II) ions produced varied coloured precipitates. This precipitate was allowed to cool, filtered, and then cleaned with 50% pure alcohol and distilled water. These complexes were dried for two hours at 70 °C in a dry hot air oven. The resulting complex gives up to 65-78 % of the yield.
Synthesis of Nanoparticles: The synthesis of nanoparticles was carried out by mixing a metal ions solution with Schiff base at an equimolar concentration of 0.02M. The mixture was then refluxed for three hours, transferred to a test tube, and centrifuged in a machine at room temperature for over three hours at 5000 RPM. Coloured crystals' excellent power was attained. Following their separation and drying, these crystals were kept at room temperature in a covered container. The purpose of these nanoparticles was characterization.
Characterization: Measurements of magnetic susceptibility were performed using HgCO (CNS)₄ as a calibrant. Using KBr pellets, FTIR was recorded on a Perkin Elmer FTIR -8400 Spectrometer (4000-400cm-1). A Cintra-5 GBC UV-visible spectrophotometer was used to record UV-visible spectra. On a Mettler Toledo Star System, TGA (thermogravimetric analysis) and DTA (differential thermal analysis) measurements were made between 50°C and 1000°C when atmospheric nitrogen was present. Using the Maxis Impact (Bruker) mass spectrometer, ligand and complexes mass spectra were taken. An Elico conductivity bridge was used to test conductivity. SEM and TEM data were obtained at the nanoparticles because it finds dispersed electrons on the particle surface by using Quanta 200 ESEM is the instrument by Icon Laboratory Mumbai, An elemental analysis was carried out in the laboratory.
RESULT AND DISCUSSIONS: The table below lists the Schiff base complexes' analytical and physical parameters. All complexes are coloured and thermally stable at room temperature, with the exception of Zn(II). While complexes are soluble in DMSO and DMF, the Schiff base is soluble in ethanol, methanol, butanol, acetone, and benzene. The complexes broke down at high range temperatures between 237 and 254 °C, whereas the Schiff bases melted between 175 and 178 °C. The MP and DP were obtained in an uncorrected open capillary setting. The complexes were shown to be non-electrolytic based on their molar conductance measurements in DMSO at 10-3 M concentration 22-23. Pd(II) and Pt(II) were measured using AAS techniques, and the metal concentrations were determined using 0.01M EDTA with various indicators 24.
TABLE 1: PHYSICAL AND ANALYTICAL PARAMETERS (*EXPERIMENTAL)
Schiff base/ Complexes | % Yield | MP/ DPºC | C% | N% | M% | Ω-1 ol‐1 cm2 | BM.μeff |
(C14 H11 ClN2O2) | 93 | 175-178 | 61.21 | 10.20 | - | - | - |
60.85* | 10.03* | - | |||||
[Mn(C28 H20 Cl2N4O4).2H2O] | 72 | 241-244 | 52.68 | 07.78 | 08.61 | 4.38 | 5.28 |
52.40* | 07.59* | 08.38* | |||||
[Co(C28 H20 Cl2N4O4). 2H2O] | 75 | 245-248 | 52.37 | 07.72 | 09.17 | 4.44 | 4.22 |
52.17* | 07.58* | 09.01* | |||||
[Ni(C28 H20 Cl2N4O4). 2H2O] | 68 | 250-253 | 52.17 | 08.73 | 09.14 | 4.98 | 3.30 |
52.02* | 08.59* | 08.98* | |||||
[Cu(C28 H20 Cl2N4O4). 2H2O] | 65 | 247-250 | 51.98 | 08.66 | 09.82 | 5.01 | 1.80 |
51.82* | 08.51* | 09.68* | |||||
[Zn( C28 H20 Cl2N4O4). 2H2O] | 78 | 240-243 | 51.83 | 08.64 | 10.08 | 4.98 | Dimag |
51.70* | 08.48* | 09.92* | |||||
[Pt(C28 H20 Cl2N4O4). 2H2O]
[Pd(C28 H20 Cl2N4O4). 2H2O] |
69
71 |
248-251
243-246 |
43.20 | 07.20 | 25.06 | 4.92
4.97 |
-
- |
43.05*
48.75 48.59* |
07.02*
08.12 07.98 |
24.90*
15.43 15.27* |
Infrared Spectra: IR spectra offer important insights into the characteristics of a functional group that is joined to a metal atom. To investigate metal complexes using the Schiff coupling mode base. Table 2 data of pertinent infrared bands that offer strong structural support for the ligand and complexes formation. The ligand and its substituted moieties were compared with the complexes' infrared spectra. All metal complexes have large bands assigned to them in the infrared spectrum 3489 cm-1 and 3414 cm-1, which suggests the existence of two coordinated water molecules.
The >C = N- vibration is the cause of the band at 1642 cm–1 in the free Schiff base. This group's shift in metal complexes to a lower frequency (1606-1529 cm-1). When contrasted to the free ligand in metal complexes, indicates that the nitrogen atom azomethine group coordinates the metal ion 25-26.
The Schiff base's amino group peak, which is located at 3391 cm-1, will be moved to lower frequencies in complexes that fall between 3136 cm-1. The atom would reduce the azomethine bond's electron density, which would reduce –HC=N–absorption.
In any metal complex when the oxygen atom of the carboxylic group is involved in the bond with metal ions (deprotonation of the carboxylic group), the band at 3385 cm-1 is attributed to the carboxylic ion 27. The complexes' spectra showed new bands absent from the ligand's spectrum in the range 574-550 cm-1 bands corresponding to vM-N and 475–492 cm-1 to νM–O vibrations, respectively 28-29. These bands supported the involvement of carboxylic groups of oxygen, nitrogen of azomethine, and amino group complexation with metal ions 30.
In complexes in the 1307 cm-1, the frequency of the ligand's carboxylic stretching is seen at 1318 cm-1 and is moved to a lower frequency area, indicating bonding via carboxylic oxygen.
Thus, >C=N-, amino and -COO- are the coordination sites of the metal ion, as shown by the IR spectrum data. The central metal ions have eight coordination numbers and the ligand behaves as bidentate 31.
FIG. 1: IR OF (A) SCHIFF BASE AND (B) NI(II) COMPLEX
SEM, TEM and EDX: The SEM, TEM, and EDX micrographs of complexes are shown below figures. The SEM and TEM images of these complex molecules are arranged in granular shape with spherical shape structure 32. The particle size of the prepared complexes is between 16-84 nm. EDX analysis shows that the complex has corrected elements that are present in prepared complexes.
FIG. 2: SEM, TEM AND EDX OF MN(II) COMPLEX
Electronic Spectra: The assessment of outcomes provided by alternative structural inquiry techniques frequently benefits greatly from the use of electronic absorption spectra. Based on the locations and quantity of d-d transition peaks, the stereochemistry of the metal ions in the complexes was determined using electronic spectrum measurements 33.
Using acetone as a solvent, the electronic absorption spectra of the Schiff base and its Mn(II), Ni(II) and Cu(II)) complexes were recorded at ambient temperature. In the electronic spectra of the Cu(II) complex, a single wide band is seen at 16,666 cm–1 (600 nm) and 25974 cm–1 (385 nm), corresponding to the 4T1gà4A2g(P), and 4T1gà4T2g transitions, respectively. These transitions are consistent with octahedral geometry. The Mn(II) complex's electronic spectra revealed two spin-allowed transitions at 12315 cm–1 (812 nm), 17856 cm–1 (560 nm), and 21734 cm–1 (460 nm), respectively. These transitions are attributed to 4T1g→4T2g(F), 4T1g→4A2g(F), and 4T1g→4Tg(P), and they are consistent with the octahedral arrangements for the Co(II) ion.
An octahedral geometry for the Ni(II) complex is supported by the emergence of a band at 24509 cm–1 (408 nm), 19230 cm–1 (520 nm), and 13123 cm–1 (762 nm) due to its assignments 3A2g à3T1g(P), 3A2g à 3T1g and 3A2gà3T2g transitions 34-35. The nephelauxetic effect, covalence parameter b1/2, and co-valence (δ%) parameters were calculated 36 &11 and listed in the below table.
TABLE 2: ELECTRONIC SPECTRA
Complexes | Bands (nm) | β | 1-β | ƞ | b 1/2 | δ% |
[Co(C28 H20 Cl2N4O4). 2H2O] | 382,590 | 0.9775 | 0.0225 | 0.0116 | 0.1060 | 1.1662 |
[Ni(C28 H20 Cl2N4O4). 2H2O] | 450,530,645 | 0.9798 | 0.0202 | 0.0104 | 0.1004 | 1.0410 |
[Cu(C28 H20 Cl2N4O4). 2H2O] | 432,542 | 0.9802 | 0.0198 | 0.0102 | 0.0994 | 1.0201 |
FIG. 3: UV-VISIBLE OF A) NI(II), B) CU(II), C) CO(II) COMPLEXES AND D) ESR SPECTRA OF CU(II) COMPLEX
ESR Spectra: The distribution of unpaired electrons and consequently, the kind of bonding between the metal ion and its ligands are revealed by ESR spectrum analysis of paramagnetic transition metal (II) complexes. Many publications have been published on the use of ESR to analyze square-planar or deformed octahedral complexes of [Cu(C28 H20 Cl2N4O4). 2H2O] and how the covalency of the metal-ligand bonding is interpreted based on the ESR parameters 37.
As seen in figure the Cu(II) complex displayed nicely resolved anisotropic signals in both the parallel and perpendicular areas. The table displays the observed data, which indicates that g|| = 2.37 and g| = 2.0928. The Cu(II) complex appears to have significant distortion from octahedral symmetry, as shown by the g|| values being larger than g| 38.
The function g|| is somewhat sensitive to covalency. In M-L bonding, an anionic environment is characterized by g|| > 2.4 and a covalent environment by g|| < 2.4. The Cu(II) complex's measured g||values are smaller than 2.4, which is consistent with the M-L bond's covalent nature. On the other hand, the Cu(II) complex displayed g||> 2.4, a feature indicative of an anion environment. The complexes exhibit a trend of g||> g| > 2.0020, indicating that the unpaired electron is located in the dx2-y2 orbital of the Cu(II) ion. For the complexes, a tetragonal shape is therefore suggested 39.
The exchange interaction between the metal centers in a polycrystalline solid is measured by the axial symmetry parameter G= (g||-2)/(g|-2), which has been determined. If G>4, there is little exchange interaction, and if G<4, there is significant exchange interaction in the complexes.
Mass Spectra: To examine the stoichiometry composition of the (C14 H11 ClN2O2) Schiff base and its metal complexes, room-temperature ESI mass spectra are employed. The [M] peak's estimated m/z of 274.70 matches to the Ligand [L] molecular ion peak at m/z 274.7. While the mass spectra of the two compounds, [Ni(C28 H20 Cl2N4O4). 2H2O] shows theoretical m/z is 642.08 and [Mn(C28 H20 Cl2N4O4). 2H2O] = is 612.28 m/z respectively, which corresponds to the molecular weight of the respective compounds. These peaks attest to the complexes' structural integrity and validate the metal chelates' [ML2] type stoichiometry.
The fragmentation of the metal complex molecule resulting from the rupture of various bonds inside the molecule by successive degradation is responsible for the various molecular ion peaks that appear in the mass spectra of complexes. This formation of various radicals leads to the formation of many more significant peaks 40. Molecular ion peaks in complex spectra are consistent with the structure inferred from elemental analysis, spectroscopic, and magnetic investigations.
FIG. 4: MASS SPECTRA OF A) SCHIFF BASE AND B) NI(II) COMPLEX
TGA/DTA: The findings of the differential thermal analysis and thermogravimetric analysis of [Pt(C28 H20 Cl2N4O4). 2H2O] are presented as below. Because of the exothermic and endothermic processes, complexes lose weight. These compounds break down in several stages and are thermally stable at room temperature. The Pt(II) Complex breaks down into four stages. In the first stage, one water molecule and a portion of the chelate are lost at temperatures between 30-135 ºC. The organic moiety and another water molecule an intermediate species are lost at temperatures between 135-295 degrees Celsius. The mass loss corresponds to the formation of intermediate species through the decomposition of some part of the complex's organic moiety in between 300-425 ºC and finally the complex decomposition is caused and formed by the metal oxides at higher temperatures, specifically in the 430-775 ºC temperature range. This process continues until a constant weight is reached, at which point a mixture of manganese oxide residue is produced. The above complex's decomposition is illustrated in as below;
FIG. 5: TGA DTA OF PT (II) COMPLEX
Microbial Activity: The Schiff base Ligand(L-1) shows less activity against all the micro-organisms while its Cu(II), Pd(II) and Pt(II) complexes show higher activities compared to Mn(II) and Ni(II) complexes. The Mn(II) complex shows moderate activities against all bacteria.
TABLE 3: MICROBIAL ACTIVITY
Ligand/ Complexes | Gram-Positive Bacteria | Gram-Negative Bacteria | ||
S. aureus | B. subtilis | E. coli | S. typhi | |
(C14 H11 ClN2O2) | 14 | 17 | 15 | 17 |
Mn(II) Complex | 17 | 19 | 18 | 20 |
Ni(II) Complex | 18 | 20 | 19 | 21 |
Cu(II) Complex | 22 | 24 | 23 | 26 |
Pd(II) Complex | 21 | 23 | 22 | 24 |
Pt(II) Complex | 23 | 27 | 24 | 26 |
FIG. 6: COMPLEX STRUCTURE
CONCLUSION: Using a condensation reaction, 3-{(Z)-[(2-aminophenyl) methylidene] amino}-4-chlorobenzoic acid was converted into Schiff base with their metal ion complexes created. The link between the nitrogen of the imino, amino groups and the oxygen of the carboxylic group was shown bonding with metal ions in the IR spectra of the complexes. The complexes are covalent. The central metal ions have eight coordination numbers and the ligand behaves as bidentate. The study also shows that the coordination sphere contains two coordinated water molecules. Cu(II), Co(II), and Ni(II) complexes of the Schiff base and its electronic absorption spectra were recorded and showed covalent bonding. The parameters like the Nephelauxetic effect, covalence parameter b1/2, and co-valence (δ%) are calculated. Cu(II) & Ni(II) complexes had an octahedral geometry with weak covalent bonding. The different ESR spectrum parameters are computed. The complexes' mass spectra match the ligand and complexes' theoretical masses.
ACKNOWLEDGMENTS: The authors would like to thank the Management of PTVA, HOD, Chemistry, and the Principal for providing the necessary research facilities. SEM, TEM, and EDX were recorded at the ICON laboratory, Mumbai TGA/DTA facilities from CMET Pune.
CONFLICT OF INTEREST: No conflicts of interest regarding this investigation.
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How to cite this article:
Kapade MG, Batawale PP, Dalvi UM and Lokhande MV: Synthesis and characterization of noval schiff base complexes of MN(II), CO(II), NI(II), CU(II), ZN(II), PD(II), PT(II) metal ions for microbial activities and their nanoparticles. Int J Pharm Sci & Res 2024; 15(11): 3297-06. doi: 10.13040/IJPSR.0975-8232.15(11).3297-06.
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Article Information
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3297-3306
1008 KB
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English
IJPSR
Manisha G. Kapade, Pooja P. Batawale, Uttara M. Dalvi and Manohar V. Lokhande *
Department of Chemistry, Sathaye College (Autonomous), Vile Parle East, Mumbai, Maharashtra, India.
manohar2210@gmail.com
11 June 2024
26 June 2024
17 July 2024
10.13040/IJPSR.0975-8232.15(11).3297-06
01 November 2024