Conseguences of soil crude oil pollution on some wood properties of olive trees Chemistry |58 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 Microwave Preparation, Spectral Studies and Antimicrobial Activities Evaluation of Mn (II) ,Ni (II) , Hg (II) ,Co (II) and Cu (II) Complexes with Schiff Base Ligand Rehab Kadem Rahem Al-Shemary Dept. of Chemistry/College of Education for Pure Science)Ibn Al- Haitham(University of Baghdad Email:drrehabalshemary@gmail.com Received in:19/June/2016,Accepted in:12/December/2016 Abstract New Schiff base and their Mn(II),Co(II),Ni(II), Cu(II) and Hg(II) complexes formed by the condensation of O-phathaldehyde and ethylene diamine (2:1) to give ligand (L 1 ) in the first step ,then the ligand (L 1 ) with 2- aminophenol (1:2) to give ligand (L 2 ) were prepared by classic addition through microwave method . These compounds (Ligands and complexes) have been diagnosed electronic spectra, FT-IR, 1 H-& 13 C-NMR (only ligand), magnetic susceptibility, elemental microanalysis and molar conductance measurements. Analytical values displayed that all the complexes appeared (metal: ligand) (1:1) ratio with the six chelation. All the compounds appear a high activity versus four types of bacteria such as; (Escherichia coli), (Staphylococcus aureus),(Bacillus btilis), (Staphylococcus aureus) and (Pseudomonas aeruginosin). Keywords: Microwave Preparation, Complexes for Schiff base, O- Paraldehyde, and Antimicrobial activities. Chemistry |59 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 Introduction In every day of life, the improved pharmaceuticals in coordination chemistry have a large interdisciplinary relation for transition metal ion that are used to control the harmful effects of fungi and bacteria [1-8]. The studies about behavior ligands in the chelation with transition metal ions by using the microwave as assisted were considered as one of the important properties in green chemistry [9]. The application of microwave- supported preparation continues to develop in organometallic [10], coordination [11] and organic chemistry pace [12]. The reactions in Microwave-irradiated show using shorter reaction times, less amount of solvent or solvent-free conditions present low cost, good yield, minimum pollution, simplicity in handling and processing[13].By microwave approaches, there is little literature on the preparation of metal complexes [14,15] Materials: All the used chemicals O-phathaldehyde, ethylene diamine, 2-amino phenol, glacial acetic acid, HBr ,CaCl2 and reagents and solvents such as ethanol, methanol in addition to various metal chlorides were obtained from Sigma-Aldrich. Instrumentation Electronic spectra were recorded using UV-Vis. spectrophotometer type CECIL, England, by using quartz cell has path length (1cm) in range (200-1000)nm in DMSO at room temperature. Melting point was measured by "Gallenkamp Melting point Apparatus". Elemental microanalysis C.H.N. was carried out using Euro Vector EA 3000 A Elemental Analysis (Italy). FT-IR measurements were calculated on Shimadzu- 8300, Spectrophotometer in the range of (4000-400cm -1 ) as KBr disc. In DMSO by using a Bruker 300 MHZ (Switzerland) were obtained on ( 1 H and 13 C-) NMR spectra, Chemical shift was obtained in δ(ppm) unit downfield internal reference (TMS), Conductivity measurements were obtained from WTW conductivity meter by using ethanol as a solvent of 10 -3 M concentration at room temperature. Magnetic susceptibility measurements were obtained at room temperature on the solid state applying Faraday's Method using Bruker BM6 instrument. Metal analyses of complexes were determined by using a Shimadzu PR- 5.GRAPHIC PRINTER atomic absorption spectrophotometer. Conventional technique for the preparation of the ligand [5] (L 1 ) was synthesized by the condensation of (1:2) molar ratio of ethylenediamine (0.060g, 0.001mmole) and O-paraldehyde (0.268g, 0.002 moles) with 3droup glacial acetic acid dissolved in(15mL) ethanol. The product mixture was refluxed for 4 h on a water bath and then left to cool overnight. The colored solid result of the ligand was filtered, washed with hot ethanol many times and dried at room temperature in air and finally desiccated under low pressure in desiccators. m.p. 171°C. Yield: 67 %. H2N NH2 + O O N O O N ref lux 4hrs. ethanol/GAA 1 2 Synthesis of [L2]: (L2) was synthesized by the condensation of (1:2) molar ratio of ( L1) (0.0292 g,0.001 mmole) with 2-aminophenol (0.218 g,0.001 mmole) dissolved in (15mL) ethanol. The product reaction mixture was refluxed for 3 h on a water bath and then left to cool overnight. The colored result of the ligand was filtered, washed with hot ethanol several Chemistry |60 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 times and dried in air at room temperature and finally stored under low pressure in desiccators. m.p. 183 °C; Yield: 70 % scheme(2) N O O N + H2N N N N N 2 HOOH OH ref lux4hrs Ethanol/HCl1 Microwave technique for the synthesis of the Schiff bases Synthesis of [L1] :(2:1) molar ratio of O-paraldehyde (0.268g) with ethylenediamine (0.06 g) was mixed in a grinder completely. The mixture in the microwave oven was then irradiated by taking 3-4 mL of absolute ethanol as a solvent. The reaction was finished in a distilled time (4–5 min) with more yields than were got in the conventional procedure. Then the results were recrystallized from ethanol and finally dried in desiccators over anhydrous CaCl2under low pressure. (yield: 80 %). Synthesis of [L2]: The [L2] has prepared according to the method synthesis of [L1] scheme(2) by(2:1)( 2-aminophenol :L 1 :) molar ratio (0.380g) was mixed in a grinder completely. The mixture in the microwave oven was then irradiated by taking (3–4 mL) of absolute ethanol as a solvent. The reaction was finished in a shortened time (4–5 min) with more yields than were got in the conventional procedure. Then the results were recrystallized from ethanol and lastly dried in desiccators over anhydrous CaCl2under low pressure. Conventional technique for the synthesis of metal complexes All the complexes were synthesized by blending 10 mL of a methanolic solution of (10 mM) salt {(1.98 g MnCl2.4H2O , 2.38 g CoCl2.6H2O, 2.37 g NiCl2.6H2O, 1.72g CuCl2.2H2O, and 2.71 g HgCl2)} with 10 mL a methanolic solution of (10 mM) the Schiff base (L 2 ) in{ (metal: ligand) (1:1) }ratio, then refluxed mixture for 1 h on a water bath. The precipitated complexes were filtered, washed several times with ethanol and dried under low pressure in a desiccator over CaCl2. Also by using an electric oven they were further dried the results were at 55–70 °C. Microwave technique for the synthesis of metal complexes The metal salts and the ligand and were mixed in a grinder in a {(metal: ligand) (1:1)} ratio. In the irradiated oven, the mixture was irradiated by taking 3–4 mL ethanol solvent. The mixing was finished in a shortened time (2-3 min) with more yields than were get in the classic method. Then the results were recrystallized from 2ml of {ethanol, methanol, and distilled water} and finally dried in desiccators over anhydrous CaCl2under low pressure. Chemistry |61 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 N N N N O O M M=CoII, NiII,CuII,MnII&HgII Antimicrobial activity The antimicrobial activity(in vitro)of the realized ligand and their metal chelates were examined against the four types of bacteria as (Escherichia coli and Staphylococcus aureus, Pseudomonas aeruginosin) by the disc diffusion method using nutrient agar as the medium using a micropipette in ethanol and the plate was incubated at 37 °C 24 h. After incubation, we measured the samples that considered as the inhibitory power of the specified test bacterial [4]. Results and Discussion As an outcome of the irradiated -supported preparation, the time of reaction showed that it was diminished from more hours to little minutes also got good yields of the results were received looked at those fulfilled by the customary preparation method. In the microwave method, rotation of mixture platform tray makes reaction mixture more homogeneity. The repetition of the preparation process to make sure the results [3] . All the metal complexes are characterized by the following data. Based on the elemental analysis the composition of metal complexes and percentage of various elements help to formulate the complexes. They were solid, colored and disintegrated on warming at rising of the temperatures and were less or more solvent in basic organic solvents. The data of a comparison of the two preparation techniques showed that reactions which were completed 5.2–6.8 min by the microwave methods but were demanded 4.6–7.20 h by the conventional method and the yields were got better 61.8–75.8 % to 76.2–85.4 %. . Molar conductivity All the complexes had stoichiometry for (ligand: metal) was (1:1). The watched molar conductance of metal chelates at room temperature in ethanol, were shown in Table 5. They were consistent with the non-electrolytic nature of all the complexes [2,3]. NMR spectra 1 HNMR spectrum: All signals in the integral intensities of the 1HNMR spectrum of ligand Figure (3) were found to agree with the number of the following signals: DMSO at δH 2.479, CH2 at δH 5.38; C6H5 as multiple at δH7.31~8.28; HCO carbonyl group at δH10.38 .The peaks observed at δH 8.78 and δH 8.85 are attributable to the HC=N amine group present in the ligand [5]. 13 C NMR spectrum: in DMSO-d6 solution shows the following signals Figure (4): DMSO at 40.8;CH2 at 56.70, 61.84; =C-N at 101.41, C6H5 as multiple at 128.50~141.13. The peaks observed at 160.05 and 192.87are attributable to the C=N imine group, and C=O carbonyl group C=N imine group, respectively [6].The characteristics frequencies of the free and mixed ligand complexes of the metals are given in Table (4). Chemistry |62 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 The IR data support these assignments IR spectrum of the ligand displayed the generality characteristic frequencies due to(C=N) azomethine and (C–O) groups and showed in the formed ligand, NH2, and C=O bonds were disappeared. The free ligand spectrum, Figure (1) displayed band at (3441) cm –1 is attributed to the deformation and stretching of the phenolic OH. These bands were disappeared in the spectra of the complexes [7]. The two bands at (1678, 1620) cm –1 attributed to the two azomethine groups of the ligand, after complexation, these bands were shifted to lower frequencies in the region (1668-1661) cm –1 and (1617-1614) cm –1 , elucidating the bonding of nitrogen atoms of (C=N) imine groups to the metal ions. This can be illustrated by the granting of electrons from nitrogen to the vacuous d-orbital of the metal atom[8]. The phenolic C–O stretching vibration that showed at (1211) cm –1 in the ligand, this band was shifted towards higher frequencies about (22–16) cm –1 in the complexes, Figure (2). This suggests deprotonation of the phenolic OH group after its coordination with the metal ion[9]. This shift confirms the participation of oxygen in the C–O–M bond. In the low-frequency region, the band of weak intensity observed for the complexes in the region (567-555) cm –1 is attributed to M–O and in the region (474- 438) cm –1 is attributed to M–N. The IR data of both the Schiff base and their metal complexes showed that the Schiff base was the type of hexadentate ligand through chelated to the metal ion [10]. Electronic spectra and magnetic moment The U.V- Vis spectra values of the metal complexes in ethanol solution are observed in Table 6. The (U.V- Vis) spectrum for the ligand, exhibits a high intense absorption band at {(275) nm}{ (36363) cm -1 } and a small peak at (385) nm (25974) cm -1 , which assigned to (π→π*), and (n→π*) transitions, respectively [11]. The electronic spectrum [Co(L 2 )], displays five peaks, the peaks at 1={(910) nm}{(10989)cm -1 },2={(657)nm}{(15220)cm -1 }and{3=(486)nm} (20576)cm -1 }due to{ 4 T1g(F)→ 4 T2g(F))},{ 4 T1g(F)→ 4 A2g(F)}and{ 4 T1g(F)→ 4 T1g(P)} transitions, and the high absorptions at {(292) nm}{(34246) cm -1 }and {(397)nm}{ (25188)cm -1 }are assigned to the (L.F) and (C.T) transitions, which suggest the octahedral geometry for Co(II) complex [12]. The room temperature magnetic moment (µeff = 4.58B.M) corresponded to a high spin octahedral symmetry. The (U.V- Vis) spectrum [Ni(L 2 )], exhibits four bands, the peaks at {1= (668) nm} {(14970)cm -1 }due to{ 3 A2g(F)→ 3 T1g(F)},{2=(543)nm}{(18416)cm -1 },{ 3 A2g(F)→ 3 T1g(P) } transitions and the high peaks at {(280) nm}{(35714)cm -1 }and {(392)nm}{ (25510) cm -1 } for the (L.F) and (C.T) transitions[13] . Ni (II) complex showed an amount of µeff = 2.98 B.M, which suggests an octahedral geometry around the central metal ion. The (U.V- Vis) spectrum [Cu(L 2 )] displays three peaks, the band at{ 1= (530)nm}{(18867)cm -1 } due to{ 4 Eg → 4 T2g} transitions and the high peaks at {(280)nm}{ (35714) cm -1 } and {(392)nm}{(25510) cm -1 and {(269) nm}{(37174)cm -1 } due to (L.F) and (C.T) transitions, on an octahedral geometry [14]. Cu (II) complex exhibited a value of µeff =1.83 μB. The (U.V- Vis) spectrum of [Mn(L 2 )] showed three peaks, the peak at{ 1= (553)nm}due to {(18083)cm -1 }{ 6 A1g(s)→ 4 T1g(G)},and the high peaks at {(279)nm} {(35842)cm -1 }and {(394)nm}{(25380)cm -1 }are assigned to the (L.F) and (C.T) transitions in an octahedral geometry[15] . Mn(II) complex exhibited a value of µeff =5.51μB. The (U.V- Vis) spectrum [Hg(L 2 )], exhibits two high peaks at{(310) nm}{(32258) cm -1 } and {(412)nm}{ (24271)cm -1 } are due (L.F) and (C.T) transitions .The Hg (II), complex did not Chemistry |63 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 show any peak in the vis. The region, no ligand field absorptions band were appeared, therefore the absorptions observed in the spectrum of the complex could be assigned to transition from type charge transfer. In fact this produced a good convention with past study of octahedral geometry[16].Hg(II)complex measured magnetic susceptibility and showed diamagnetic as a perspective from their electronic arrangement (d 10 ) . Antimicrobial activities The antimicrobial activities in vitro of the prepared ligand and their corresponding metal complexes against bacteria such as Escherichia coli and Staphylococcus aureus , Pseudomonas aeruginosin were established in Table(5). All compounds are checked and displayed better antimicrobial activity versus the microorganism [17]. On comparing it was shown that the activity of the complexes had moderate as compared to the standard but all the complexes were more active than their single ligand. The greater inhibition zone of the complexes than the free ligand can be expounded based on the chelation theory and the Overtone concept. The interfere of the partial sharing of the positive charge of the metal ion and the ligand orbital with donor groups are due to reduce the polarity of the metal ion in upon chelation. Furthermore, this enhances the blocking of the metal binding sites and the penetration of the complexes into lipid membranes in the enzymes of microorganisms that the delocalization of the π-electrons increases up to the full coordination ring[18]. Conclusion One of a green chemical path is the microwave technique. The prepared compounds were diagnosed by spectral analyses and different chemical-physic. In route of the microwave helped syntheses, it was spotted that the time of reaction was decreased from many hours to few minutes and the results were obtained in good yield as a comparison to those of the conventional method. The metal ions bound with the diagnosed hexadentate ligand type N4O2 in six donor sites are present four N- azomethine and two O- phenylic. References 1. Rehder, D.; Santoni, G.; Licini, G. M. and Schulzke, Meier, C. B.; (2003), Vanadium- Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles, Coord . Chem. Rev. 237, 53. 2. Sharma, R.; (2013),Synthesis, Characterization and antimicrobial activity of bis(γ- amino bu tyro hydroxamate) oxovanadium(IV) , Asian J. of Adv. Basic Sci.: 1(1), 45-50. 3. Neven, S.;Boris-Marko,K.and Zora, P.,(2012),Preparation,spectroscopic, structural, and thermal characterization of vanadium complexes with 2 -quinaldic acid, Adv. Mat. Lett. 143, 11, 1471-1477 4. Jain, R.K., and Anand P.M.; (2012), Microwave synthesis and spectral, thermal and antimicrobial activities of some novel transition metal complexes with tridentate Schiff base ligands , J. Serb. Chem. Soc.,77 (8) 1013–1029 5. Jin, Y.H.; Pyo Lee, M.; and Lah, M. S.; (2014) A linear trinuclear mixed valence vanadium (V/IV/V) complex: Synthesis, Characterization And Solution Behavior, Ulsan National Institute of Science & Technology , 7:04:29.7. 6. Arijit, H.; Barik, A.K.; Sachindranath, P.; Samik, G.; Somnath, R.; Ray, J. B.; Shie-Ming, P.; Lee, G.H. and Susan, K. Kar; (2007)Synthesis and structural studies on di-oxovanadium(V) complexes of N(4)-substituted pyrazole based thiosemicarbazones, Polyhedron, 26 773–781. http://link.springer.com/journal/706/143/11/page/1 Chemistry |64 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 7. Meena, R. and Fahmi, N.; (2013), New nematicidal active compounds: Design and eco- friendly, synthesis and characterization of oxovanadium (V) complexes with Schiff base ligands, Inter. J.Biotech. Bioeng. Rese., 4, 5, 437-444. 8. Mishra, R.; Jain, R.and Gupta, S.; (2012), Synthesis of New VO(II), Co(II), Ni(II) and Cu(II) Complexes with Isatin-3-Chloro-4-Floroaniline and 2-Pyridine carboxyl indene- 4- Aminoantipyrine and their Antimicrobial Studies, Microbiology; 40(1): 20–26. 9. Chaudhary, N.K.and Mishra, P.;(2015),Spectral Investigation and In Vitro Antibacterial Evaluation of Ni II and Cu II Complexes of Schiff Base Derived from Amoxicillin and α-Formyl thiophene (αft), J. of Chemistry, 12,176-181 . 10. Mishra, A.P.; Tiwari, A. and Rajendra, K.; (2012), Microwave-induced synthesis and Characterization of Semiconducting 2- thiophene carboxaldehyde Metal Complexes , Adv. Mat. Lett. 3(3), 213-219 11. Saad, F. A. and Khedr, A. M.; (2015), Azo-azomethine Ligands with N2O2 Donor Atom Sets and their Binuclear UO2(II) Complexes: Synthesis, characterization and biological activity Bulgarian Chemical Communications, 47, 2 654-663, 12. Rajendra, K. and Mishra, A. P.; (2012) ,Microwave synthesis, spectral, thermal, and antimicrobial activities of some transition metal complexes involving 5- bromosalicylaldehyde moiety, Current Chemistry Letters 1, 163–174 13. Khedr, A. M. and Saad, F.A.;(2015), Synthesis, structural characterization and antimicrobial efficiency of sulfadiazine azo-azomethine dyes and their bi-homonuclear uranyl complexes for chemotherapeutic use, Turk J Chem , 39: 267-280 14. Revankar, D. S., Ajani, J. C., Revanasiddappa, M.; Swamy M. V.and Shankar S.; (2014),Synthesis, Characterization, and Biological Studies on Riluzole Schiff base Metal Complexes ,J. Appl. Chem., 3 (4):1447-1459 15. Jain,R. and Mishra, A. P.; (2012),Microwave assisted synthesis, spectroscopic, Thermal and Antimicrobial Studies of Some Transition Metal Complexes of Schiff base ligands containing thiazole moiety , Jordan J.of Chem.,7,1, 9-21 16. Jignesh, P. H.; Jadeja, R. N. and Ganatra , K. J. ;(2014),Spectral characterization and biological evaluation of Schiff bases and their mixed ligand metal complexes derived from 4,6-diacetylresorcinol, J. Saudi Chem.Soc., 18, 3, 190–199, 17. Nalawade, A.M.; Nalawade , R.A.; Patange, S.M. and Tase, D.R.; (2013), Thiazole Containing Schiff bases and their transition metal complexes, Inter. J. of Engin. Sci. The invention, 2 (7), 01-04. 18. 17. Mishra, A. P.; Mishra, R.; Jain, R.and Gupta, S.; (2012) Synthesis of new VO(II), Co(II), Ni(II) and Cu(II) complexes with isatin-3-chloro-4-floroaniline and 2-pyridine carboxylidene-4-aminoantipyrine and their antimicrobial studies, Microbiology , 40(1): 20– 26, 19. Meena R. and Fahmi, N.; (2013), New nematicidal active compounds: Design and ecofriendly, synthesis and characterization of oxovanadium (V) complexes with Schiff base ligands, Inter. J.Biotech. Bioeng. Rese., 4, 5, 437-444 , http://www.ncbi.nlm.nih.gov/pubmed/?term=Mishra%20R%5Bauth%5D http://www.ncbi.nlm.nih.gov/pubmed/?term=Jain%20R%5Bauth%5D http://www.ncbi.nlm.nih.gov/pubmed/?term=Gupta%20S%5Bauth%5D http://www.hindawi.com/19353179/ http://www.hindawi.com/51271648/ http://www.sciencedirect.com/science/article/pii/S1319610311001293 http://www.sciencedirect.com/science/article/pii/S1319610311001293 http://www.sciencedirect.com/science/article/pii/S1319610311001293 http://www.sciencedirect.com/science/journal/13196103/18/3 http://www.ncbi.nlm.nih.gov/pubmed/?term=Mishra%20AP%5Bauth%5D http://www.ncbi.nlm.nih.gov/pubmed/?term=Mishra%20R%5Bauth%5D http://www.ncbi.nlm.nih.gov/pubmed/?term=Jain%20R%5Bauth%5D http://www.ncbi.nlm.nih.gov/pubmed/?term=Gupta%20S%5Bauth%5D Chemistry |65 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 Table (1): The physical and analytical data of ligand(L 2 ) and metal complexes[M(L 2 )] compounds Formula Molecular Weight Colour Yeild% Conventional M.P. %Elemental Analysis Found % (Calculated) Microwave C H N M L 2 C30H26N4O2 474.55 Light brown 70.5 201-203 75.93 (75.23) 5.52 (5.31) 11.81 (10.85) - 82 [Co(L 2 )] C30H24CoN4O2 531.47 Brown 74 229-231 67.80 (59.50) 4.55 (4.84) 10.54 (8.67) 11.09 (9.12) 80.3 [Ni(L 2 ) ] C30H24N4NiO2 531.23 Brown 65.8 220-222 67.83 (59.52) 4.55 (4.84) 10.55 (8.68) 11.05 (9.09) 76.2 [Cu(L 2 ) ] C30H24CuN4O2 536.08 Deep brown 61.8 235-237 67.21 (59.07) 4.58 (4.80) 8.34 (8.61) 9.45 (9.77) 78 [Mn(L 2 ) ] C30H24MnN4O2 642.0 Brown 72 226-228 59.08 (59.87) 4.26 (4.87) 8.33 (8.73) 7.89 (8.56) 85.4 [Hg(L 2 ) ] C30H24HgN4O2 788.17 Off-White 75.8 222- 224 48.00 (48.80) 3.64 (3.97) 8.89 (8.32) 25.45 (25.47) 79.7 Table (2) 1 H-NMR chemical shifts for ligand (L 2 ) (ppm in DMSO) Table (3): 13 C-NMR chemical shifts for ligand (L) (ppm in DMSO) DMSO 2HC 5H6C =NC =OC 40.82 56.70 61.84 128.50-141.13 160.05 192.87 Table (4): The important IR bands of the Ligand(L 2 ) and it's metal complexes[M(L 2 )] Compound υ(OH) υ(CH)aroma. υ(CH)alph a υ(C=N) υ(C=C) υ (C-O) υ (M–N) υ(M–O) L 2 3441 3032 2916 1678 1620 1598 1211 - - [Co(L2)] - 3012 2920 1670 1617 1590 1227 567 468 [Ni(L2)] - 3006 2931 1666 1616 1595 1233 558 474 [Cu(L2)] - 3024 2947 1662 1614 1592 1229 561 438 [Mn(L2)] - 3003 2918 1664 1615 1597 1228 565 459 [Hg(L2)] - 3005 2927 1663 1613 1589 1230 555 461 Table (5): Zone of inhibition of growth in 100 millimeters after 24 hours of incubation pseudomonas Bacillus Staphylococcus aureus Escherichia. Coli Comp. 1 - - 2 L 2 11 12 10 6 [Co(L 2 )] 9 10 11 8 [Ni(L 2 )] 7 11 9 10 [Mn(L 2 )] 6 8 7 7 [Cu(L 2 )] 8 7 6 9 [Hg(L 2 )] DMSO 2HC 5H6C HC=N COH 2.47 5.38 7.31-8.28 8.78 8.85 10.38 Chemistry |66 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 Table (6):Electronic spin resonance parameters of the complexes Compound µeff ᴧm S.Cm 2 molar -1 λnm υ–wave number cm –1 Assignments L 2 - - 275 36363 π→π* 385 25974 n→π* [Co(L2)] 3.98 17.8 292 34246 L.F 397 25188 C.T 486 20576 4 T1g(F)→ 4 T1g(P) 657 15220 4 T1g(F)→ 4 A2g(F) 910 10989 4 T1g(F)→ 4 T2g(F) [Ni(L2)] 3.57 14.5 280 35714 L.F 392 25510 C.T 543 18416 3 A2g(F)→ 3 T1g(P) 668 14970 3 A2g(F)→ 3 T1g(F) [Cu(L2)] 1.83 12.6 286 34965 L.F 390 25641 C.T 530 18867 4 Eg → 4 T2g [Mn(L2)] 5.51 12.7 279 35842 L.F 394 25380 C.T 553 18083 6A1g(s)→ 4 T2g(G) [Hg(L2)] Dia 16.9 310 32258 L.F 412 24271 C.T Figure (1): The IR spectrum of (L 2 ) Figure (2): The IR spectrum of the [Co(L 2 )] complex Chemistry |67 https://doi.org/10.30526/30.3.1602 7302(عام 0العدد ) 03مجلة إبن الهيثم للعلوم الصرفة والتطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (3) 2017 Figure (3): The 1 H-NMR spectrum of (L 2 ) Figure (4): The 13 C-NMR spectrum of (L 2 ) Figure (5): Variance between the antimicrobial activity of (L 2 ) and their complexes 0 5 10 15 L2[Co(L2)][Ni(L2)][Mn(L2)][Cu(L2)][Hg(L2)] Escherichia. Coli Staphylococcus aurous Bacillus pseudomonas