Synthesis and characterization of p-Toluic hydrazide and o-Hydroxy Acetophenone Schiff base and its metal complexes

 

G.N. Raja Reddy*, S. Kondaiah  and J. Sree Ramulu

Department of Chemistry, Srikrishnadevaraya University, Anantapur, Andhra Pradesh, India.

*Corresponding Author E-mail:  nagarajareddygodula@gmail.com

 

The chemistry of metal complexes with tailor made Schiff base ligands and their applications have aroused considerable interest because of preparative accessibility, diverse reactivity and structural variability. A novel Schiff base ligand OHAPPTH (p-Toulic Hydrazide and o-Hydroxy acetophenone Schiff base) and its Mn (II), Co (II), Ni (II) and Cu (II) metal complexes have been synthesized and characterized by various physio chemical methods viz. FT-IR, H¹-NMR, UV-Visible, ESR, VSM, Molar conductance, XRD and micro analytical data and found to be anti bacterial activity. The magnetic properties of these Mn (II), Co (II), Ni (II) and Cu (II)  complexes are 5.25 B.M. 4.80 B.M., 3.06 B.M and 1.68 B.M respectively. This result clearly indicates that the metal complexes of this ligand show octahedral geometry. The IR spectrums of these Schiff base metal complexes shows bands at 1603cm^-1, 1588cm^-1 1612cm^-1 and 1598cm^-1 respectively, which is assigned to (C=N) stretching vibrations, a fundamental feature of azomethine group. The structural assessment of these complexes has been carried out based on above physio-chemical and spectroscopic methods. These Schiff base and its metal complexes show a good activity against E. coli and Basillus subtiles. The anti bacterial results also indicate that the metal complexes are better antibacterial agents as compare to the Schiff base.

 

 

 

1. INTRODUCTION:

The preparation of a new ligands was a perhaps the most important step in the development of metal complexes which exhibit unique properties and novel reactivity. Schiff base were important class of ligands, such ligands and their complexes had a variety of applications including biological, clinical, analytical and industrial in addition to their important roles in catalysis and organic synthesis.¹ Schiff base ligands have an affinity for transition metals such as Cu, Mn, Co and Fe. Maihub et al.³ (2005) prepared and investigated some Schiff base complexes of Co (II), Ni (II) and Cu (II) ions. It is found that prepared complexes have square planar structures. The Ben Saber et al.² (2005) reported the synthesis and characterizations of Cr (III), Fe (II), Co (II) and Ni (II) complexes with a Schiff base derived from 4-dimethyl amino benzaldehyde and primary amines. The chemical analysis data showed the formation of (1:1) metal  ligand  ratio and a squre planar geometry was suggested for Co (II) and Ni(II) complex while an octahedral structure  for Cr(III) and Fe(III) complexes.^4-5

                  

 Here we are report the synthesis and characterization of p-Toluic hydrazide and o-Hydroxy Acetophenone Schiff base and its Mn (II), Co (II), Ni (II) and Cu (II) metal complexes by using physiochemical techniques.

 

2. MATERIALS AND METHODS:

2.1 Materials and Methods                   

All materials used in this investigation were purchased from AR Loba, AR (Qualigenes), sigma/Aldrich and SRL (sisco) and used as received. They include Sodium hydroxide, p-Toulic hydrazide, o-Hydroxy acetophenone, methanol and double distilled water was used during the experimental procedures. IR spectra were recorded with a Perkin-Elmer IR-598 spectrometer (4000-400 cm^-1) using KBr pellets. The ¹H NMR spectra of the ligands and their metal complexes are recorded on an AV-400 M-HZ NMR spectrometer in IICT, Hyderabad in DMSO-D₆ and CDCl₃ solvents at room temperature. The absorbances are measured on Elico SL UV-Visible spectrophotometer. The ESR spectra for all Cu (II) complexes were recorded at room temperature and at liquid nitrogen temperature (LNT) on a Bruker ESP 300E spectrometer in IIT Mumbai. The ESR spectrum obtained from the instrument is a plot of the first derivative of the absorption curve as a function of the magnetic field which was calibrated with an NMR gauss meter and the exact frequency was determined using DPPH radical as a field maker.

 

Magnetic susceptibility data was recorded on an EG and G-155 magneto meter.  Thermo gravimetric analyses of the metal complexes were carried out by using the Perken Elmar System in thermal analysis center:  STIC KOCHIN. The molar conductance measurements were carried out in DMF using conductivity meter model CM Elico-185.

 

2.2 Synthesis of p-Toluic hydrazide and o-Hydroxy Acetophenone Schiff base (OHAPPTH):

 

Mixture of p-Toluic hydrazide (1.50g) and o-Hydroxy Acetophenone (1.36 ml) were dissolved in 30 ml methanol and added a pinch of NaOH. The whole mixture was transferred in to 100 ml round bottom flask. The mixture was refluxed about 2 hours on water bath. When the reaction mixture was allowed to cool light brown needles were obtained. The compound was recrystalized from water. The %of yield was 83% and melting point of the compound was 188-190 ⁰C.

 

Scheme – 1 Synthesis of p-toluic hydrazide and o-Hydroxy acetophenone Schiff base

 

2.3 Synthesis of Mn (II), Co (II), Ni (II) and Cu (II) metal complexes of p-Toluic hydrazide and o-Hydroxy Acetophenone Schiff base (OHAPPTH):

These complexes were prepared by adding requiste (2g (0.0074moles)) amount of Schiff base in 50ml of 50% methanol to the Mn (II), Co (II), Ni (II) and Cu (II) metal ions (0.0074moles) in distilled water in the presence of Sodium acetate and stirred about 10hours. Yellow, Greenish black, dark brown and Green color precipitates of metal complexes were obtained with good yield. These products were washed several times with hot water cold methanol to remove unreacted ligand and metal slats respectively. Finally, all these complexes were dried in vacuum over calcium chloride desiccator.

 

3. RESULTS AND DISCUSSION:

3.1 IR Spectral Studies:

The Infrared spectrum of the OHAPPTH ligand is compared with the spectra of its Mn (II), Co (II), Ni (II) and Cu (II) complexes. The important and specific IR spectral frequencies along with their assignments are given in Table 1. The IR spectras are shown in Fig.1 (a-b).          A strong band exhibited at 1654 cm^-1 in the IR spectrum of the ligand has been assigned to the (C=N) Stretching vibration of the azomethine group. On complexation this band is shifted to 1603cm^-1, 1588cm^-1 , 1612cm^-1 and 1598 cm^-1 for Mn (II), Co (II), Ni (II) and Cu (II) complexes respectively.⁶ This shift to lower wave numbers supports the participation of the azomethine group of this ligand in binding to the metal ion. The coordination of azomethine nitrogen to the metal atom would be expected to reduce the electron density in the azomethine group and thus cause for a reduction in C=N stretching frequency. Bands appeared at 3192 and 1390 cm^-1 due to the stretching and bending vibrations of phenolic OH respectively.⁷ These bands are disappeared in spectra of complexes indicating the deprotanation of phenolic OH. This is further confirmed by the appearance of new bands in the region 440-509 cm^-1 and 570-661 cm^-1, which are assigned to the stretching frequencies of M-N and M-O of the metal ligand bands respectively for Mn (II), Co (II), Ni (II) and Cu (II) complexes. The IR spectrum of the ligand has shown a band in the region 1450-1550 cm^-1 due to the C=C stretching vibrations. A weak band observed around 2900 cm^-1 in both ligand and complexes could be assigned to the C-H stretching frequency. A broad band exhibited at 3320 cm^-1 in the IR spectrum of the ligand due to N-H stretching vibration. On complexation this band shifted to 3329, 3328, 3327 and 3326cm^-1 for Mn (II), Co (II), Ni (II) and Cu (II)   complexes respectively. The IR spectrum of the ligand has shown a sharp band at 1704 cm^-1 due to C=O stretching vibration. On complexation this band shifted to 1691, 1678, 1684 and 1687cm^-1 for Mn (II), Co (II), Ni (II) and Cu (II) complexes respectively⁸. These results indicate the formation of complex.

 

The IR spectra of Mn, Co, Ni and Cu complexes exhibited broad bands at 3410 cm^-1,  3390 cm^-1, 3402 cm^-1 and 3420  cm^-1  respectively which can be assigned to the OH stretching vibration of the coordinated water molecules. These results indicate that the ligand coordinate with the metal ion through the azomethine nitrogen and the oxygen of the deprotonated hydroxyl group.

 

Table 1. Important IR bands of OHAPPTH ligand and its metal complexes

Compound	OH Water	OH Phenolic	C=N	N-H	C=O	M-O	M-N
OHAPPTH	-	3192	1654	3320	1704	-	-
OHAPPTH-Mn	3410	-	1603	3329	1691	648	509
OHAPPTH-Co	3390	-	1588	3328	1678	661	440
OHAPPTH-Ni	3402	-	1612	3327	1684	570	441
OHAPPTH-Cu	3420	-	1598	3326	1687	593	482

 

 

Fig 1a: IR Spectrum of OHAPPTH Ligand

 

Fig 1b: IR Spectrum of OHAPPTH-Cu(II) metal complex

 

3.2. NMR Spectral Studies:

Fig.2 (a-b) shows the NMR spectra of the OHAPPTH ligand and its metal complexes. Table 2 contains the important chemical shift values along with their assignments. The ¹ H NMR spectrum of the OHAPPTH ligand showed a singlet at 2.57 ppm which can be assigned to the methyl protons attached to azomethine(C=N) group. The singlet appeared at 2.41ppm is attributed to the methyl protons of the phenyl ring. A multiplet is observed in the region 6.94-7.89 due to the aromatic protons of phenyl rings. A singlet appeared at 13.51 ppm is attributed to the hydroxyl proton attached to the phenyl ring in the ligand. The singlet appeared at 11.25 ppm due to N-H proton of ligand. In the  ¹H NMR spectrum of the OHAPPTH –Co complex, a signal appeared due to methyl protons attached to  azomethine group has been shifted to 2.92 ppm compared to 2.57  ppm in the case of ligand . This down field shift indicates the deshielding of azomethine proton on coordination through nitrogen atom of azomethine group⁹. The signal observed at 2.41 ppm due to the methyl protons in the ligand is shifted to 2.69 ppm for the Co complex. The singlet appeared at 13.51 ppm due to phenolic hydroxyl proton is absent in the NMR spectrum of Co complex indicating the deprotonation of hydroxyl group and the involvement of that oxygen in coordination. A new signal is observed as a singlet at 3.90 ppm in the case of Co (II) complex indicating the presence of water molecules coordinated to the metal atom. The multiplet observed in the region 6.94-7.89 ppm due to aromatic protons for the ligand showed a shift to 6.80-8.01 ppm for Co complex¹⁰ may be due to the drifting of ring of electrons towards the metal ion. A signal observed at 11.25 ppm due to the N-H proton in the ligand is shifted to 11.34 ppm for the Co complex. In the  ¹H NMR spectrum of the OHAPPTH –Cu complex, a signal appeared due to methyl protons attached to  azomethine group has been shifted to 2.98 ppm compared to 2.57  ppm in the case of ligand. This down field shift indicates the deshielding of azomethine proton on coordination through nitrogen atom of azomethine group. The signal observed at 2.41 ppm due to the methyl protons in the ligand is shifted to 2.58 ppm for the Cu complex. The singlet appeared at 13.51 ppm due to phenolic hydroxyl proton is absent in the NMR spectrum of Cu complex indicating the deprotonation of hydroxyl group and the involvement of that oxygen in coordination¹¹. A new signal is observed as a singlet at 3.85 ppm in the case of Cu (II) complex indicating the presence of water molecules coordinated to the metal atom. The multiplet observed in the region 6.94-7.89 ppm due to aromatic protons for the ligand showed a shift to 6.61-7.89 ppm for Cu complex may be due to the drifting of ring of electrons towards the metal ion. A signal observed at 11.25 ppm due to the N-H proton in the ligand is shifted to 11.42 ppm for the Cu complex.

 

 

Table: 2 ¹H NMR Spectral data of OHAPPTH ligand and its metal complexes

Compound	H3C-C=N	Ar-H	CH3	Ar-OH	N-H
OHAPPTH	2.57	6.94-7.89	2.41	13.51	11.25
OHAPPTH-Co	2.92	6.80-8.01	2.69	-	11.34
OHAPPTH-Cu	2.98	6.61-7.89	2.58	-	11.42

 

Fig 2a: H¹ NMR Spectrum of OHAPPTH Ligand

 

Fig 2b: H¹ NMR Spectrum of OHAPPTH-Cu(II) metal complex

 

3.3 UV-Spectral studies:

The electronic spectra of the aqueous solutions of Mn^+2, Co⁺², Ni⁺²  and Cu⁺² individual ions are compared with the corresponding ligand nature^12-13. The data is given in Table 3. The data indicates that the energy of the d-d transitions in the complexes is slightly less when compared to the corresponding aqua ions either because of slight covalent interaction of the 3d vacant orbitals with ligands, leading to some delocalization with consequent reduction in inter electronic repulsion or by increased nuclear shielding of the orbitals due to slight covalent ligand-metal electron drift.

The transition for the ligand occurred at 291 nm. But on complexation with the different metal ions like Manganese, Cobalt, Nickel and Copper new bands appeared at 380 nm, 389 nm, 375 nm and 395 nm respectively corresponding to the transitional charge transfer from the ligand to the different metal ions. Bands occurred in the region of 370-410 nm for all complexes are assigned to charge transfer transition (L→ M). Based on the results octahedral structure is proposed for Mn⁺² , Co⁺² , Ni⁺² and Cu⁺² complexes.

 

Table: 3 Electronic spectral data of OHAPPTH ligand and its metal complexes

Compound	λmax of compound
OHAPPTH	291
OHAPPTH-Mn	380
OHAPPTH-Co	389
OHAPPTH-Ni	375
OHAPPTH-Cu	395

 

3.4. ESR Spectral studies of OHAPPTH-Cu complex:

Only one broad signal is exhibited in the ESR spectra of the complexes in polycrystalline state, which is attributed to dipolar broadening and enhanced spin lattice relaxation. Anisotropic spectra obtained for all complexes in DMF at LNT and representative ESR spectra of OHAPPTH-Cu (II) ion complex is presented in Fig.3. In this low temperature spectrum, four peaks of small intensity have been identified which are considered to originate from g_ǁ component. The spin Hamiltonian, orbital reduction and bonding parameters of OHAPPTH-Cu complex are presented in Table.4

The g_ǁ and g_⊥ are computed from the spectrum using DPPH free radical as g marker. Kivelson and Neiman have reported that g_ǁ value is less than 0.08 for covalent character and is greater than 2.3 for ionic character of the metal-ligand bond in complexes. Applying this criterion, the covalent bond character can be predicted to exist between the metal and the ligand complexes^14-15. The trend g_ǁ > g_ave> g_⊥>2.0023 observed for the complex suggests that the unpaired electron is localized in d_x2_-y2 or d_z2 orbital of the Cu (II) ions for the complexes. The G values for Copper complex are given in Table.4. It is observed that the G value of present complex is greater than four and suggest that there are no interactions between Copper-Copper centers in DMF medium.

 

The ESR parameters g_ǁ , g_{⊥ ,} A_ǁ^* and A_⊥^*  of the complexes and the energies of d-d transitions are used  to evaluate the orbital  reduction parameters ( K_ǁ ,K_⊥ ), the bonding parameters ( α²), the dipolar interaction (P) . The observed K_ǁ < K_⊥ indicates the presence of out of plane bonding. The α² value for the present chelate is 0.531. It indicates that the complex have covalent character. This shows an appreciable covalency in the inplane σ bonding.  Girdano and Bereman suggested the identification of bonding groups from the values of dipolar term P. The reduction of P values from the free ion value (0.036cm^-1) might be attributable to the strong covalent bonding. The value of P obtained for the present complex is 0.0156 cm^-1 and remain consistent with bonding of Copper ions to oxygen and nitrogen donor atoms respectively. The shape of ESR lines, ESR data together with the electronic spectral data suggest¹⁶ an octahedral geometry for OHAPPTH-Cu complex.

 

Fig 3 ESR Spectrum of OHAPPTH-Cu (II) Metal Complex

Table: 4 ESR Spectral data of OHAPPTH-Cu complex

Parameters	OHAPPTH-Cu
g║	2.25749
g⊥	2.06142
gave	2.12677
G	4.19228
A║*	0.01931
A⊥*	0.00523
Aave*	0.00992
d-d	16154
K║	0.618
K⊥	0.761
P*	0.0156
α 2	0.531

 

 

Table :5 Thermal Analytical Data of the OHAPPTH    metal complexes

Complex X=H2O	Molecular Weight in grams	Weight of the complex taken in mgs	Stage	Temperature range in oC	Probable assignment	Mass loss (%)	Total mass loss (%)
Mn L2 2X L=C16 H16 O2N2	625.57	8.00	1 2 3	131.91  to 221.13 280.15 to 553.69 Above 667.55	Loss of 2H2O molecules Loss of 2L molecules Corresponds to MnO	5.754 79.17 15.07	84.924
Co L2 2X L=C16 H16 O2N2	629.56	7.50	1 2 3	140.24 to 252.17 281.44 to 562.96 Above 612.45	Loss of 2H2O molecules Loss of 2L molecules Corresponds to CoO	5.718 84.80 9.48	90.518
Ni L2 2X L=C16 H16 O2N2	629.269	8.00	1 2 3	115.14 to 264.49 294.61 to 613.80 Above 650.94	Loss of 2H2O molecules Loss of 2L molecules Corresponds to NiO	5.720 81.56 11.61	87.28
Cu L2 2X L=C16 H16 O2N2	634.086	8.00	1 2 3	110.82 to 238.05 290.69 to 522.60 Above 550.00	Loss of 2H2O molecules Loss of 2L molecules Corresponds to CuO	5.677 82.542 11.670	88.219

 

 

3.5. Magnetic susceptibility measurements of OHAPPTH complexes:

The magnetic moments of the present OHAPPTH Mn (II), Co (II), Ni (II) and Cu (II) complexes are 5.25, 4.80, 3.06 and 1.68 BM.  The magnetic moments of this ranges are suggest octahedral geometry for Mn (II), Co (II), Ni (II) and Cu (II) complexes¹⁷. 

 

3.6. Thermal behavior of Mn (II), Co (II), Ni (II) and Cu (II) Metal complexes of OHAPPTH

The Thermo gravimetric studies of all the complexes were carried out in air at a heating rate of 10⁰C per minute. The thermo analytical data is summarized in Table.5. The thermal decomposition of the complexes proceeds in three stages. The Mn (II), Co (II), Ni (II) and Cu (II) complexes are thermally stable up to 131, 140, 115 and 110^oc respectively. The first stage of decomposition corresponding to endothermic dehydration of complexes by the loss of two water molecules occurs in the temperature range 131-221^oc, 140-252^oc, 115-264⁰C and 110-238^oC respectively^18-19. The intermediates formed are stable up to 280, 281, 294 and 290⁰C . The second decomposition with exothermic peak by the loss of ligand moiety occur in the temperature range 280-552^oc, 281-562^oc, 294-612^oc and 290-522^oC. The solid residues above 667, 612, 650 and 550⁰C were identified as Mn (II), Co (II), Ni (II) and Cu (II) metal oxides respectively. In all the complexes, the final products are metal oxides.

 

3.7. Conductivity Measurements of OHAPPTH metal complexes:

The molar conductance data of complexes in DMF at10^-3 are presented in Table 6. The molar conductance values are 6.24, 5.70, 8.10 and 5.44 ohm^-1 cm²mol^-1 respectively for OVPTH-Mn (II), OVPTH-Co (II), OVPTH-Ni (II) and OVPTH-Cu (II). The complexes are found to be non electrolyte in DMF solution.

 

Table: 6 Molar conductivity of Vanadium, Manganese, Cobalt, Nickel and Copper complexes   

Metal complexes	Molar conductance(ohm-1 cm2mol-1)
OHAPPTH-Mn	6.24
OHAPPTH-Co	5.70
OHAPPTH-Ni	8.10
OHAPPTH-Cu	5.44

 

3.8. Powder XRD study of OVPTH-Cu Complex

The powder X-ray diffraction data obtained for OHAPPTH-Cu complexes with difractograms using DROL-2 powder diffractometer. Radiation filled by metal foil. The diffractogram (22 diffractions) reflects Fig 4 between 3-80 (2θ) values for Cu complex. Where θ is Brages angle all the main peaks are indicted and calculated values of Miller indices (h k l) along with observed d-specified and reveled intensities are specified in the Fig: 4. All the peaks have been indexed 2θ values compared in graph. Comparison values revels that there is good agreement between values of 2θ and d-values. The powder x-ray diffraction data showed identical features with very poor crystalinity. The patterns are qualitative and dispersive in intensity for Cu (II) complex²⁰. The XRD patterns are used to explain qualitatively the degree of crystalinity. X-ray Diffraction data of OHAPPTH-Cu complex are presented in   Table 7.

 

Fig 4: XRD Spectrum of OHAPPTH-Cu(II) Metal Complex

 

3.9 Anti bacterial activity

The biological activity of the OHAPPTH ligand and their complexes were tested against bacteria because bacteria can achieve resistance to anti biotic through bio chemical and morphological modifications. In this study, all the synthesized compounds were evaluated for their in vitro antibacterial activity against two bacterias namely E.coli and B. subtiles. A comparison of antibacterial activity of the synthesized compounds with that of standard drugs was effectively presented in Table 8. Streptomycin was used as a reference drug. The antibacterial activity results^21-22 indicate that most of the metal chelates exhibited good to moderate antibacterial activity when compared to streptomycin. Among the synthesized metal complexes OHAPPTH-Cu showed high activity.

 

 

 

Table.7. X-ray Diffraction data of OHAPPTH-Cu complex:

S.No.	d expt	d Calc	2θ expt	2θ Calc	h k l
1	12.1110	12.1052	7.2931	7.2657	3 3 1
2	7.0351	7.0329	12.5718	12.5613	4 3 2
3	6.5995	6.5862	13.4045	13.4026	5 3 0
4	5.9659	5.8963	14.8369	14.7929	4 4 3
5	5.4657	5.4243	16.2033	16.2012	5 4 2
6	4.5611	4.4926	19.4442	19.4318	7 4 0
7	4.1907	4.1623	21.1823	21.0942	7 5 3
8	3.6532	3.6219	24.3431	24.2987	8 5 4
9	3.2941	3.2693	27.0452	27.0186	8 8 1
10	3.1093	3.1067	28.6852	28.6639	9 6 5
11	2.5919	2.5630	34.5766	34.4762	11 8 5
12	2.3539	2.2986	38.2014	38.1986	12 10 3
13	1.9778	1.9634	45.8418	45.7930	14 13 1
14	1.6209	1.5873	56.7460	56.7370	16 14 6

 

Table 8.  Antibacterial activities of ligands and their transitions metal complexes (Zone of inhibition in mm)

Compound	E. Coli	B. Subtiles
OHAPPTH ligand	6	6
OHAPPTH-Mn (II)	-	8
OHAPPTH-Co (II)	12	8
OHAPPTH-Ni (II)	9	7
OHAPPTH-Cu (II)	14	10
Streptomycin	22	24

 

Table 9 Analytical data of the OHAPPTH ligand and its metal complexes

Molecular Formula X=H2O	Molecular Weight	Colour	Yield in %	Melting Point in 0C	Elemental analysis
					Carbon %		Hydrogen %		Nitrogen %		Metal %
					Calc	Found	Calc.	Found	Calc.	Found	Calc.	Found
L=C16 H16O2N2	268.315	Light brown	85	188-190	71.55	71.21	5.96	5.42	10.43	10.02	-	-
[Mn.2.2X]	625.57	Thick green	81	302-315	61.38	61.02	5.43	5.25	8.95	8.46	8.78	7.81
[Co.L2.2X]	629.56	Dark brown	79	290-305	60.99	60.45	5.40	5.22	8.89	8.29	9.36	8.52
[Ni. L2.2X]	629.269	Dark brown	75	282-298	61.02	60.82	5.40	5.09	8.90	8.53	9.32	8.67
[Cu.L2.2X]	634.086	Green	82	280-310	60.56	59.98	5.36	5.11	8.83	8.37	10.00	9.13

 

4. CONCLUSION:

In the present research studies, our efforts are synthesized of some newly compounds. These synthesized compounds characterized by various physio- chemical and spectral analyses. On the basis of spectral data, 1:2 stoichiometry was found for the metal: ligand. Non-electrolytic nature of the studied complexes showing the anions is coordinating to the central metal ion. By using above all spectral studies it is concluded that they behave as bidentates during complexation. The IR, ESR, and Electronic spectral studies support an octahedral geometry for all complexes.  OHAPPTH Schiff base are coordinate to the metal ion in bidentate manner with ON donor sites of azomethaine nitrogen and phenolic oxygen. Based on the spectral data proposed geometry for all the complexes are depicted in Fig.4.The results of in –vitro biocidal activities of the ligand and its metal complexes clearly show antibacterial activity against the tested organisms. On the basis of chelation theory, metal complexes have more biological activity than free ligands.

              

Fig.4. OHAPPTH Metal Complex M=Cu⁺², Co⁺², Ni⁺², Mn⁺²

 

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Received on 07.01.2012         Modified on 25.01.2012

Accepted on 12.02.2012         © AJRC All right reserved