Synthesis and application of antioxidant and antimicrobial properties of azomethine and its complexes

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SYNTHESIS AND APPLICATION OF ANTIOXIDANT AND ANTIMICROBIAL PROPERTIES OF AZOMETHINE AND ITS COMPLEXES

Rahimova Aysel R.

Department of Chemistry, Baku State University,

Baku, Azerbaijan

Abstract. A three compounds, p-aminobenzylden-a-naftylamine and its metal complexes have been successfully prepared. The complexes obtained are characterized by using IR, NMR, EPR spectroscopy. It has been established that they have shown a high antioxidant properties and are inhibitors of complex action. Studies have shown that the investigated metal complexes are effective inhibitors of the oxidation of complex action: Terminated chain oxidation reaction with peroxide radicals and hydroperoxide are catalytically decomposed Azomethine derivatives have been found to be more effective standarts oxidants as the process dominantly affects the overall antioxidant behavior of. The investigation of antimicrobial properties show that these compounds behaive like high antimicrobial agents.

Keywords: Azomethine, antioxidant properties, metal complexes.

Introduction.

Schiff bases derived from an amino and carbonyl compound are an important class of ligands that coordinate to metal ions via azomethine nitrogen and have been studied extensively. In azomethine derivatives, the C=N linkage is essential for biological activity.The literature survey reveals that the metal complexes and derivatives have nucleus enhanced pharmaceutical, agricultural and industrial values so, the medicines containing azomethine nucleus are now used extensively in medical, biomedical and biotechnological facililties [1]. It has been shown to posses industrial, fungicidial, insecdicidial, medicinal values. The synthetic applications of azomethine derivatives have been investigated and shown to have enough potential in the synthesis of nitrogen and sulfur containing heterocyclic compounds [2].Some derivatives of azomethine posses antituberculoses, anticancer, antitumor, antipyretic activities. These drugs have been shown to posses a diverse range of physiological activities, plant growth, promoting activity, antitumor, antibacterial, antidiabetic values[3,4]. Some azomethines were also found to be active against S. aureus, E. coli, and C.albicans[5]. In the literature it is known that a number thiocarbamides and their various derivatives are widely used in industry as a monomers, copolimers, corrosion inhibitor, herbicides and fungicides in agriculture .

antioxidant effect synthesized metal

Experimental Part.

IR spectra were investigated by use of UR-20 spectrometr.

P-aminobenzylidenen-a-naftylamine

The ligand was synthesized by the condensation of p-aminobenzaldehyde and a-naftylamine in 1:1 molar ratio using absolute alcohol as the reaction medium. The mixture was refluxed on water bath for 1 and a half an hour and then allowed to stand overnight at room temperature. The product was crystallized from the same solvent.

Melting point- 112 ⁰C, yield-68 %.

IR spectra (v, sm^-1): 1650 (C=N), 1610 (C=C), 1470, 1180 (C-N (CHs)2. NMR spectra (8, ppm): 8.146 (C=N), 3.641-3.028 (CHs^N, 2.050 (4H), 1.205-1.131 (CH2).

The IR spectra of the complexes C=N zone is observed at 1650 sm^-1. In comparison with its position in the spectrum of the ligand (1637 sm^-1) it is shifted to low-frequency zone. Such a change proves presence of coordination of metal with N atom C=N bond (635-620 sm^-1, M=N). On the base of above-mentioned we can conclude that complexes should have such a structure: M(L)2X2, where X-anion.

The complex of Cu(II) (II).

They were prepared by reacting ethanolic solution of the ligand with ethanolic solution of metal acetate in 1:2 molar ratio. The precipitated solid coloured complexes were filtered, washed with ethanol, dried in oven. Melting point-155 ⁰C, yield- 62 %.

The complexes of Ni (II) (II)

They were prepared by reacting ethanolic solution of metal acetate in 1:2 molar ratio. The settled down solid coloured complexes were filtered, washed with ethanol, dried in oven. Melting point- 148 ⁰C, yield-60 % ..

Antimicrobial properties

Antimcrobial activity of the compounds of tested against using Pseudomonas Aeruginosa, Mycobacterium lacticolium, Aspergillus niger, Cladasporium resinale, Penicillium Chrosegenum, Chastomium gloloodium Trichoderma viride. The sterilized (autoclaved 121⁰ C for 15 min) medium (40-50⁰) was poured into the Petri dishes to give a depth of 3-4 mm and allowed to solidly. The suspension of the microorganism the steaked on plates.The paper discs impregnated with the test compounds was placed on the solidified medium.The plates were pre-incubated forth at room temperature and incubated at 37⁰ C for 24 hour.

Table 1

(I-III) RESEARCHING OF FUNCTIONAL PROPERTIES OF COMPOUNDS

Synthesized compounds show high antimicrobial properties in a low concentration. If we compare antimicrobial properties ligand and metal complexes, metal complexes show higher , than ligand. However the structure of metal complexes get difficult, properties increases.

Antioxidant properties

Antioxidant effect of synthesized metal complexes studied in model reactions. As a model reaction initated by a-a'-azobisizobutylnitrole (AlBN) used oxidation reaction in a solution of chlorobenzene at 60⁰C. Inhibitory properties of the compounds studied the kinetics of the reaction with radicals cumylperoxde and cumylperoxide cumyl. Chlorobenzene, cumyl and cumyl hydroperoxide was purified by the standart procedure.

Reaction with radicals cumylperoxide studied initiates (AIBN) cumyl oxidation in the presence of these compounds. Initiator was injected at a concentration of 2xl0^-2 mol/l inhibitor concentration was 5x10^-5 mol/l. Reaction cumyl hydroperoxide with metal complexes was performed in a glass reactor thermostated at chlorobenzene solution while bubbling nitrogen. Samples periodically analyzed for cumylhidroperoxide iodometric. On the spending of ROOH measured reaction rate of interaction with hydroperoxides metal complexes. As can be seen from Figurel, with the study initiated by AIBN cumyl oxidation at 110 ⁰C in the presence of the synthesized compounds inhibited the oxidation of studied inhibitors react with radicals cumylperoxide. Studies have shown that all compound shaving as a part of metal complexes fragment inhibit initated oxidation.

It has been shown the antioxidant measurements in the table. Largest induction period (t) calculated stoichiometric factor y, equal to the number of oxidation chains terminating in one molecule of the inhibitor and its transformation products. To calculate the rate constants for the interaction of inhibitors with peroxide radicals-k7 kinetic curves of oxygen uptake of the transformed coordinates into [O2]^-1t to [O^-]^-1 t.

Table 1

ANTIOXIDAN PROPERTIES OF AZOMETHINES AND ITS METAL COMPLEXES

Figure 1 has shown cumene oxidation in the presence of the initiator kinetic curves metal complexes listed derivatives. We can see from the picture, the curves of compounds with cumolhidroperoxide. In addition to the compounds studied has not been going at a steady pace and induction period of oxidation of cumene is not observed. However, in response to a concentrated environment metal complexes into derivatives when the absorption rate of 5 10-4 moll reduced.

Figure.1 Cumene oxidation kinetic curves in the presence of synthesized compounds (I, IIIII) with initiator T = 60 0 C: 11 [InH] = 0; [AIBN] = 2 10-2 mol/1, O₂-absorbing oxygen volume (ml); T-induction period

Figure 2 under the influence of the synthesized compounds were cumene autooxidation kinetic curves. As shown in the picture cumene induced cycle inhibitor for 40 minutes. In comparison with the first picture we can see that the decomposition of cumene without initiator the period of induction equal 20 minutes. As can be seen, the highest result determined nikkel derivatives.

Figure 2. The kinetic curves of cumene autooxidation with prescence of synthesized compounds (I, II and III) T = 110 0 C: 11, [In H] = 0: [lnH} = 5 10-5 mol / l:VO2-absorbed oxygen volume (ml); T-induction period.

As a result of studies have found that all the tested compounds (1-5) actively decomposed HPC figure 3. Kinetic curve of HPC decomposition under the action of the compound consists of two parts. At the beginning of the reaction revealed some induction period during which there is very little decay HPC and then goes fast catalytic decomposition of HPC.

Figure 3. Kinetic curves of cumyl hidroperoxide division with synthesis compounds

This suggest that the reaction of the compound (1) of HPC is complex. First antioxidant reacts with cumyl hidroperixide turning into active products which are then catalytic decomposition of HPC.

The catalytic decomposition of hydroperoxide in the presence of metal complexes flows under the influence is not the source of the antioxidant and its conversion products.

The results showed that one molecule of the compound capable of decomposing to a few tens of thousands of molecules HPC. The value of the kinetic parameters of the catalytic decomposition of HPC by the action of the compounds are shown in Table 2.

Results and discussion.

In model reactions, we studied the reactions of different metal complexes with cumylperoxide and cumylperoxide radicals established that they have exhibit high antioxidant activity. Continuing studies on the synthesis of various derivatives metal complexes and studied the relationship between structure and antioxidant properties in this paper the synthesis metal complexes based on the reaction of benzaldehyde with p-aminophenol

Analysis of the kinetic parameters of the HPC cleavage is seen that the catalyst factor is observed for the compound which in the molecule, together with a azomethine moity also contains a primary amine fragment. From the table we can easily see that high antioxidant properties, along with its inherent high catalyst factor also has a high value of the reaction rate constant. For example, the value for the compounds (1) is 9 and for compounds (2-4) 2,2-5,22 l/mols.

Thus studies have shown that the investigated metal complexes are effective inhibitors of the oxidation of complex action: Terminated chain oxidation reaction with peroxide radicals and hydroperoxides are catalytically decomposed.

Conclusion

From the result of antioxidant effect we can conclude that all compounds exhibited strong to moderate activity. Metal complexes derivatives have been found to be more effective standarts oxidants as the process dominantly affects the overall antioxidant behavior of.

Acknowledgements

This work was carried out at Baku State University (BSU) (Azerbaijan), Department of Chemistry, sub-department of General and Inorganic Chemistry

References

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