IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 Synthesis and antibacterial study of the ligand type Schiff base derived from amino acid [L- Phenylalanine] and its complexes with Co (II), Ni (II), Cu (II) and Zn (II) ions M. R. Aziz Department of Chemistry, College of Education, Ibn-Al-Haitham, University of Baghdad Abstract L-Phenylalanine amino acid was condensed with 2-hydroxybezaldehyde to give the Schiff base sodium 2-(2-hydroxybenzylideneamino)-3-phenylpropanoate, which was used as a precursor [NaHL]. The precursor was reacted with 1,2-dichloroethane to give the Schiff base sodium 2,2'-(2,2'-(ethane-1,2diylbis(oxy))bis(2,1-phenylene))bis(methan-1-yl-1-ylidene)bis(azan- 1-yl-1-ylidene)bis(3-phenyl propanoate), which was used as a ligand [Na2L], in complexation with some metal (II) chloride MCl2, where [M= Co(II), Ni(II), Cu(II) and Zn(II)], to give [M(L)] complexes. The [Na2L] ligand and All complexes were characterized by spectroscopic methods, [FTIR, UV-Vis, atomic absorption], melting point, chloride content, conductivity and magnetic susceptibility measurements, as well as the Na2L ligand characterized by 1 H NMR. The data, of these studies and measurements were important to suggest an octahedral geometry around Co(II), Ni(II), Cu(II) and Zn(II) ions. The synthesized ligand, along with its metal complexes, was screened for in vitro antibacterial activity against gram-positive bacteria like Staphylococcus aureus, and Acinetobacter baumannii. This study showed an effective inhibition of gram- positive bacteria. Introduction Schiff bases have been used as chelating ligands in the field of coordination chemistry and their metal complexes are of great interest for many years [1]. Chemists have reported on the chemical, structural and biological properties of Schiff bases, Schiff bases are characterized by the -N=CH- (imine) group which is important in elucidating the mechanism of transamination and rasemination reaction in biological system [2, 3]. Schiff base metal complexes have been widely studied because they have industrial, antifungal, antibacterial, anticancer and herbicidal applications [4, 5]. They serve as models for b iologically important species and find applications in bio mimetic catalytic reactions, Schiff bases are active against a wide range of organisms, for example; Candida Albicans, Escherichia coli Staphylococcus aureus, Bacillus polymxa, the Trychophyton gypseum. Antibacterial activity has been studied more than antifungal activity , because bacterium can achieve resistance to antibiotics through biochemical and morphological modifications [6, 7]. Chelating ligands containing N, S and O donor atoms showed a broad biological activity and are of special interest because of the variety of ways in which they are bonded to metal ions. It is known that the existence of metal ions bonded to biologically active compounds may enhance their activities [8-10]. The aim of the present study is to synthesis, IHJPAS IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 characterize and evaluate the metal complexes as antibacterial agent as p romising addition of new class of complexes as metal based drugs. Experimental The used chemicals were of analytical grades; metals were used as chloride salts. The complexes were identified by atomic absorption technique, using Schimadzu (A.A) 680 G atomic absorption spectrophotometer. I.R data were recorded as (KBr) disc using Schimadzu 4800S FTIR spectrophotometer in the range (4000-400) cm -1. 1H NMR spectra were recorded in DM SO- d6 using Brucker 300 MHz spectrometer. (UV-Vis.) spectra were obtained in (MeOH) on a CECIL, CE 2700 spectrophotometer in the range (200-900) nm using quartz cell. The Magnetic measurements were carried out on solid compounds using 6 Bruker B.M instrumental. Melting points were recorded on an electro thermal Stuart apparatus and are uncorrected. Electrical conductivity measurements of the complexes were recorded at 25C˚ for 10 -3M solutions in (MeOH) as a solvent using a Wissenchaftilich tecchnich werksttaten, D1820 bweilheimI.F 42 conductivity meter. Chloride contents for complexes were determined potentiometerically by using (686-titro processor-665), Dosinat-metrom Swiss. Antibacterial screening was used agar diffusion technique [11,12]. Preparation of the ligand [Na2L] The ligand was prepared by two steps Step (1): L-phenylalanine (1 g, 6.0 mmol), was added to (10 ml), (0.24g, 6.0 mmol) sodium hydroxide-methanol solution, the mixture was stirred until a clear solution was obtained. A solution of (0.74 g, 6.0 mmol) of 2-hydroxy bezaldehyde in (10ml) methanol was added to reaction mixture, which was catalyzed with (5drops) of glacial acetic acid and stirred for (3 hours). Yellow precipitate was formed, filtered, washed with ethanol, and re-crystallized from hot methanol to give yellow crystals of the precursor [NaHL], Yield (67%), mp (225-232˚C). Step (2): A solution of the precursor [NaHL] (2.35g, 8.08mmole) in (10 ml) methanol was added to (10ml), (0.45g, 8.08mmol) potassium hydroxide-methanol solution, then a solution of (0.4g, 4.04mmole) of 1,2-dichloroethane in (10ml) methanol was added to reaction mixture was refluxed with stirring for (3 hours). Orange precipitate was formed, filtered, washed with ethanol, and re-crystallized from hot methanol to give orange crystals of the ligand [Na2L], Yield (72%), mp (260-266˚C). Preparation of [Na2L] complexes with metal ions A solution of (0.08g, 0.33mmole) of [Na2L] ligand in methanol (5ml) was added to stirred clear solution of a solution of (0.2g, 0.33mmole) of CoCl2.6H2O in (5ml) methanol. Reaction mixture was refluxed for (4 hours); dark-brown precipitate was formed, filtered and washed by water and re-crystallized with ethanol. The complexes [Ni(L)], [Cu(L)] and[Zn(L)], were obtained in a similar method to that mentioned in the preparation of [Co(L)] complex described above. Physical properties of the prepared complexes were given in (Table 1). Results and Discussion Synthesis of the ligand The ligand [Na2L] was prepared according to the general method shown in (scheme 1). The I.R spectral analysis of the precursor [NaHL], (Table 2), showed phenolic (–OH) band at (3433) cm-1, and υ(C=N) bands at (1638) cm-1, also the spectrum showed bands at (1519) cm-1, and (1404) cm-1 which assigned to υas(COO - ) and υs(COO - ) respectively and showed band at (1149) cm -1 which can be attributed to υ(C-O)phenolic group [13-17], by comparing with the I.R spectral IHJPAS IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 analysis of the ligand [Na2L], Fig(1), (Table 2), showed bands at (1635) cm-1 which assigned to υ(C=N) and band at (1219) cm-1 which assigned to ether group (C-O-C), also the spectrum showed bands at (1539) cm -1, (1404) cm-1 which assigned to υas(COO-), and υs(COO-) respectively [13-17]. Electronic spectral analysis of the precursor [NaHL], (Table 3), showed four absorption peaks at (231.5) nm εmax (2426) molar -1 cm -1 , (248.5) nm εmax (2503) molar -1 cm -1 , (316.1) nm εmax (1149) molar-1cm-1 and (404.3) nm εmax (777) molar-1cm-1, which assigned to (π→π* ), (π→π * ), (n→π * ) and (n→π * ) transition respectively [18,19]. by comparing with electronic spectral analysis the ligand [Na2L], Fig(2), (Table 3), showed four absorption peaks at (236.0) nm εmax (2395) molar-1cm-1, (259.0) nm εmax (2501) molar-1cm-1, (319.2) nm εmax (1129) molar -1 cm -1 , and (407.5) nm εmax (697) molar -1 cm -1 , which assigned to (π→π * ), (π→π * ), (n→π * ) and (n→π *) transition respectively [18,19]. 1H NMR spectral analysis of the ligand [Na2L], Fig(3), showed chemical shifts δ (ppm) of Schiff base proton (-CH=N-) at (7.9) as a singlet peak. A multiple signals at rings (6-7 and 7-7.5)ppm for phenylalanine proton and phenyl-ether proton. (-CH) proton of (-C=N-CH-) group at [3.7, 1H, t], (-CH-) methelene group at [3.4, 2H, d], and triplet peak at (4.4)ppm, which assigned to (-CH2-) in (Ph-O-CH2-) group. A singlet high peak at (4.9)ppm for the trace MeOH solvent [14,15,20,21] . Synthesis of the complexes Complexation of ligand [Na2L] with Co(II), Ni(II), Cu(II) and Zn(II) were carried out in MeOH. These complexes are stable in solution. The analytical and physical data (Table 1), and spectral data (Table 2, and 3), are compatible with the suggested structure (Scheme 1). The I.R spectra of the complexes [Co(L)](1), Fig(4), [Ni(L)](2), ([Cu(L)](3)) and [Zn(L)](4), (Table 2), exhibited the band at (1635) cm -1 in the free ligand spectrum which assigned to υ(C=N) imine group Shifted to lower frequency and appeared at (1619) cm -1, (1614) cm-1, (1617) cm-1 and (1614) cm-1 for the complexes (1),(2),(3), and (4) respectively [15-18]. These bands were assigned the υ(C=N) stretches of reduced bond order, this can be attributed to the delocalization of metal-electron density into the ligand π-system (HOMO→LUMO) [22, 23], (HOMO=Highest occupied molecular orbital, LUMO= Lowest unoccupied molecular orbital). The ether (C-O-C) stretching vibration appeared at (1219) cm -1 in the free ligand was Shifted to higher frequency and appeared at (1311) cm-1 , (1300) cm -1 , (1300) cm -1 and (1292) cm -1 for the complexes (1),(2),(3), and (4) respectively, all that indicated a linkage between oxygen of ether group and the metal [14, 22], also the spectrum showed bands at (1539) cm -1, (1404) cm-1 which assigned to υas(COO - ), and υs(COO - ) respectively in the free ligand spectrum, was shifted to lower frequency and appeared at [(1496), (1350)], [(1486), (1377)], [(1450), (1369)] and [(1480), (1373)] cm -1 for the complexes (1),(2),(3), and (4) respectively, all that indicated a linkage between oxygen of carboxylate group and the metal [24,25]. The spectra showed the appearance of bands at (460) cm-1, (482) cm-1, (478) cm-1 and (474) cm-1 refer to υ(M-N) for complexes (1),(2),(3), and (4), these bands confirm the coordination of the nitrogen atom to the metal center, while the bands at (576) cm -1, (563) cm-1, (574) cm-1 and (568) cm-1 assigned to υ(M-O) of complexes (1), (2), (3) and (4) respectively, bands confirm the coordination of the oxygen atom of carboxylate group of the ligand to metal center, and the bands at (547) cm-1, (532) cm-1, (543) cm-1 and (536) cm-1 assigned to υ(M -O) of complexes (1),(2),(3), and (4) respectively, theses bands indicating that the etheric oxygen in the ligand is involved the coordination with metal ions in complexes [22-23, 26,27]. Electronic spectral analysis of the complexes, (Table 3): Complex[Co(L)]: showed two high intense peaks at (245.5) nm εmax (2642) molar-1cm-1 and (268.6) nm εmax (2532) molar-1cm-1 were assigned to the ligand field, while a medium peak at (382.0) nm εmax (943) molar -1 cm -1 was assigned to (C.T), a weak broad peaks at (491.2) nm εmax (62) molar -1cm-1,(531) nm εmax (56) molar-1cm-1, and (622.0) nm εmax (16) molar-1cm-1, were IHJPAS IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 assigned to (d-d) electronic transition ( 4T1g(F)→ 4T2g(F)), (4A2(g)→ 4T1g), and (4T1(g)→ 4T1g(p)) respectively, suggesting octahedral geometry [19]. Complex [Ni(L)]: showed one high intense absorption at (245.5) nm εmax (2613) molar-1cm-1 are due to the ligand field, another high intense peak at (364.5) nm εmax (1825) molar-1cm-1 was assigned to (C.T), while a weak broad peaks at (450.6) nm εmax (49) molar -1 cm -1 , (510.4) nm εmax (22) molar -1cm-1, and (642.5) nm εmax (17) molar-1cm- were assigned to (d-d) electronic transition (3 A2g→ 3 T2g), ( 3 A2g→ 3 T1g), and ( 3 A2g→ 3 T1g(p)) respectively, suggesting octahedral geometry [19]. Complex [Cu(L)]: Fig(5), showed two high intense absorption peaks at (243.0) nm εmax (2624) molar-1cm-1, and (272.1) nm εmax (2543) molar-1cm-1 are due to the ligand field, a high intense absorption peak at (369.0) nm εmax (1831) molar -1 cm -1 was assigned to (C.T), while a weak broad peak at (660.5) nm εmax (41) molar-1cm-1 was assigned to (d-d) electronic transition (2E→2T2) suggesting octahedral geometry [19]. Complex [Zn(L)]: showed two peaks at (242.0) nm εmax (2537) molar-1cm-1 and (272.0) nm εmax (2315) molar-1cm-1 are due to the ligand field. While a high intense peak at (361.0) nm εmax (1763) molar -1 cm -1 was assigned to (C.T), the d 10 configuration of Zn II ion along with the data obtained confirms a octahedral structure around the ion [19]. The molar conductance of the complexes in methanol lie in the range (5.1-12.9 Ohm -1 cm - 2mol-1), (Table 3), indicting their non-electrolyte having mole ratio of metal:ligand as 1 :1 [28]. At the room temperature magnetic moments of the all complexes showed normal magnetic moment in (Table 3), the magnetic moment data were ca. (4.13), (3.25) and (1.65) B.M for Co(II) in [Co(L)], Ni(II) in [Ni(L)], Cu(II) in [Cu(L)], respectively and (0.00) B.M to Zn(II) in [Zn(L)]. The magnetic moment studies showed that these complexes were octahedral geometry [29]. Biological activity The antibacterial activity of the synthesized ligand [Na2L] and its complexes [Co(L)](1) , [Ni(L)](2), [Cu(L)](3), and [Zn(L)](4) (Table 4 and 5 ), were tested utilizing the agar diffusion technique [30]. The organism tested was staphylococcus aureus, and Acinetobacter baumannii. The agar media were inoculated with test organisms and a solution of the tested compound (100μg/ml) was placed separately in cups (6 mm diameter) in the agar medium. The inhibition zones were measured after 24 hours incubation. Separate studies were carried out with the solution alone of DM SO and the showed no activity against any bacterial strains [31]. The results of these studies revealed that the ligand and metals complexes showed an effective in the inhibition of Acinetobacter baumannii and Staphylococcus aureus. Biological activity of the previous compounds in inhibition of bacterial growth could be attributed to one of the following mechanisms, the first mechanism is by the inhibition of the bacterial cell wall synthesis by bounding to the precursor of the cell wall, and second mechanism revealed that some antibodies have similar stereo structure to substrate (D-alanyl D-alanine). So it will act competitive inhibitions for the enzymes (transpeptidase and /or carboxpeptidase) which are the main enzymes catalyzed the end step in the biosynthesis of peptidoglycans of the bacterial cell wall, other mechanisms could contributed to the results found in the study which include the inhibition of biosynthesis of bacterial proteins by linking to the ribosome by doing so, the ribosome will not be in contact with tRNA (transfer ribonucleic acid) , so the bacteria will not survive, an other mechanisms were postulated that some antibodies inhibit the denovo synthesis of bacterial DNA by sp litting DNA in DNA-enzyme complexes by inhibition DNA ligase [32-34]. References 1- Lotf ,A. Saghatforoush 1, Ali Aminkhani , Sohrab Ershad , Ghasem Karimnezhad , Shahriar Ghammamy and Roya Kabiri, (2008), “Preparation of Zinc (II) and Cadmium (II) Complexes IHJPAS IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 of the Tetradentate Schiff Base Ligand 2-((E)-(2-(2-(pyridine-2-yl)- ethy lthio)ethylimino)methyl)-4-bromophenol (PytBrsalH)”, Molecules, 13: 804-811. 2- Lau, K. Y.; Mayr, A.; Cheung, K. K., (1999), "Synhesis of transition metal isocyanide complexes containing hydrogen bonding sites in peripheral locations", Inorg. Chim. Acta, 285: 223-232. 3- Shawali, A. S.; Harb, N.M .S.and Badahdah, K. O., (1985), "A study of tautomerism in diazonium coupling products of 4- hyroxycoumrin", J. Heterocylylic Chem., 22: 1397-1403. 4- Cozzi, P.G. Metal–Salen Schiff base complexes in catalysis: Practical aspects. (2004), Chem. Soc. Rev. 33: 410-421. 5- Chandra, S.; Sangeetika, J., (2004), EPR and electronic spectral studies on copper (II) complexes of some N-O donor ligands J. Indian Chem. 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Acta 286: 134-141. 9- Canpolat, E.; Kaya, M., (2004), Studies on mononuclear chelates derived from substituted Schiff-base ligands (part 2): “synthesis and characterization of a new 5-bromosalicyliden- paminoacetophenone oxime and its complexes with Co(II), Ni(II), Cu(II) and Zn(II)” J. Coord. Chem., 57: 1217-1223. 10- Yildiz, M.; Dulger, B.; Koyuncu, S.Y.; Yapici, B.M., (2004), “Synthesis and antimicrobial activity of bis(imido) Schiff bases derived from thiosemicarbazide with some 2- hydroxyaldehydes and metal complexes”, J. Indian Chem. Soc 81,:7-12. 11 – Cruickshan, K. J.P.; Duguld, P.; Marmion, R.H.and Swain HA, ,(1975), Tests for sensitivity to antimicrobial agents. In: Medical Microbiology, 12 th edition, Churchill, living stone, Edinburgh, 190-204. 12- Clinical and laboratory standards institute (CLSI), (2005). performance standards antimicrobial susceptibility testing. Fifteenth informational supplement, CLSI document M100- S15, Wayne, USA, 13- A. 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C. and Radhakrishan, P. K. (2003), "complexes of copper with 2,3-dimethyl-4- formyl(benzhydrazide)-1- phenyl-3-pyrazolin-5-one" synthesis and reactivity in inorganic and metal – organic chemistry, 33 : (8 ) ,1307-1318. 27 - Greenwood ,N. N. and Earnshow ,A., (1998), "Chemistry of the elements," J. Wiely and sons Inc. New York. 28- Geary, W. J. (1971), “The use of conductivity measurements in organic solvents for the characterization of coordination compounds”, Coord. Chem. Rev. 7:81-115. 29- Huheey,J. E., (1994), "Inorganic Chemistry: Principles of Stracture and Reactivity" Harper International Edition, Harper and Row publishers, New York. 30- Ali, M.M, Ismail M.M.F., Al-Gaby M.S.A., Zahram M.A., and Ammar Y.A. 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VOL.23 (2) 2010 Table (1): The microanalysis results and some physical properties for the ligand [Na2L] and its complexes dec. = decompose Table (2): Infrared spectral data for the ligand [Na2L] and its metal complexes cm -1 Compounds Formula Colour M.p (˚ C) Yield% Chloride content Metal M . wt Na2L C34H30N2Na2O6 Orange 260-266 72 Nil ----- 608.59 [Co(L)](1) C34H30 N2O6Co Dark brown 285 dec. 81 Nil 8.83 (9.48) 621.54 [Ni(L)](2) C34H30 N2O6Ni Light green 279 dec. 79 Nil 8.80 (9.45) 621.31 [Cu(L)](3) C34H30 N2O6Cu Dark green 291 dec. 84 Nil 9.45 (10.15) 626.16 [Zn(L)](4) C34H30 N2O6Zn Yellowish Brown 274 dec. 68 Nil 9.70 (10.42) 628.02 Compound υ(C=N) υ(O– H) υ as(COO) υ a(COO) υ(C=C) Aromatic υ(C–H) Aromatic υ(C–H) Aliphatic υ(C– O–C) etheric υ(M– O) etheric υ(M-O) Carboxylate ion υ(M– N) NaHL 1638 3433 1519 1404 1585 3028 2939 ----- ---- ---- ---- Na2L 1635 ----- 1539 1404 1589 3028 2947 1219 ---- ----- ---- [Co(L)](1) 1619 ----- 1496 1350 1590 3028 2924 1311 547 576 460 [Ni(L)](2) 1614 ----- 1486 1377 1587 3028 2931 1300 532 563 482 [Cu(L)](3) 1617 ----- 1450 1369 1587 3028 2924 1300 543 574 478 [Zn(L)](4) 1614 ----- 1480 1373 1590 3024 2924 1292 536 568 474 IHJPAS IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 Table (3): Electronic spectral data for the ligand [Na2L] and its metal complexes Compound λ nm εmax molar-1 cm-1 Assignment Ratio Molar conductivity S.cm2.mol-1 Magnetic susceptibility B .M coordination NaHL 231 .5 248 .5 316.1 404 .3 2426 2503 1149 777 π→π* π→π* n→π* n→π* ----- ------- ------ ------ Na2L 236 .0 259 .0 319 .0 407 .5 2395 2501 1129 697 π→π* π→π* n→π* n→π* ----- ------- ------ ------ [Co(L)](1) 245 .5 268 .6 382 .0 491 .2 531 .0 622 .3 2642 2532 943 62 56 16 Ligand field Ligand field C.T 4T1g(→ 4T2g 4A2g→ 4T1g 4T1g→ 4T1g (p) neutral 8.7 3.87 (4.13) Octahedral [Ni(L)](2) 245.5 364 .5 450 .4 510 .4 642 .5 2613 1825 49 22 17 Ligand field C.T 3A2g→ 3T2g 3A2g→ 3T1g 3A2g→ 3T1g(p) neutral 5.1 2.83 (3.25) Octahedral [Cu(L)](3) 243.0 272 .1 369 .0 660 .5 2624 2543 1831 41 Ligand field Ligand field C.T 2E→2T2 neutral 5.6 1.7 (1.65) Octahedral [Zn(L)](4) 242.0 272 .0 361 .0 2537 2315 1763 Ligand field Ligand field C.T neutral 12.9 Diamagnetic Octahedral IHJPAS IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 Table (4): Biological activity of the ligand [Na2L] and its metal complexes against Acinetobacter baumannii bacteria A= Acinetobacter baumannii bacteria Table (5): Biological activity of the ligand [Na2L] and its metal complexes against Staphylococcus aureus bacteria S= Staphylococcus aureus bacteria Compound Bacteria (zone of inhibition (diameter mm)) A1 A2 A3 A4 A5 A6 A7 A8 A9 A10 Na2L 13 10 14 15 14 15 13 14 14 14 [Co(L)](1) 13 9 8 16 16 16 13 13 11 15 [Ni(L)](2) 15 9 14 16 16 17 13 Nil 13 17 [Cu(L)](3) Nil 9 14 14 13 14 12 Nil Nil 15 [Zn(L)](4) 10 10 12 13 13 17 Nil Nil 12 12 Compound Bacteria (zone of inhibition (diameter mm)) S1 S2 S3 S4 S5 S6 S7 S8 S9 S10 Na2L Nil 9 Nil Nil Nil Nil Nil Nil Nil Nil [Co(L)](1) Nil Nil Nil Nil Nil Nil 12 Nil Nil 11 [Ni(L)](2) Nil Nil Nil Nil Nil Nil Nil Nil Nil Nil [Cu(L)](3) Nil Nil 14 Nil Nil Nil Nil 8 Nil Nil [Zn(L)](4) Nil Nil 15 16 Nil Nil Nil Nil Nil Nil IHJPAS IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 Scheme (1): Preparation of the ligand [Na2L] and its metal complexes C H O H N H C H 2 C C O O N a 2 - [ (2 - h y d r o x y b e n z yl id e n e) a m in o ] - 3 -p he n y lp r o p a n o ic a ci d C H 2 CH O O C N H 2 + C H O O H H + 2 -A m i no - 3 - ph e n yl - pr o p i o ni c ac i d 2 - H y d r ox y - be n z al de h y de S o d i um h yd ro x id e M et ha n o l , m ag n et ica ll y s ti rr i n g 3 h ou rs C H 3 C O O H (5 d r op s ) + M C l 2 M e t h a n o l R e f l u x 4 H o u rs M = C o( I I ) ,N i ( I I ) , C u ( I I ) , a n d Z n( I I ) N a O H C H O H N H C H 2 C C O O N a 2 + C l C H 2 C H 2 C l d ic h lo r oe t h an e C H N H C H 2 C O C H O N C H H 2 C H 2 C H 2C C O O N a C O O N a s o d i u m 2 , 2 '- (2 ,2 ' -( e t h a n e - 1 , 2- d i y l b i s (o xy )) b i s (2 , 1- p he n y l e n e ) )b i s (m e t h a n- 1- yl - 1 -y l i d e n e ) b i s(a z a n -1 -y l - 1- y l i de ne )b i s (3 - ph e n yl p ro pa n oa t e ) C H N H C H 2 C O C H O N C H H 2 C H 2 C H 2C C O O N a C O O N a R e f l u x 3 H o u rs M e th an M eth a n o l K O H C H N C H O C H O N C H H 2 C H 2 C M H 2 C C O - O C H 2 C O O - IHJPAS IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 Fig (1): Infrared spectrum of the ligand ( Na2L ) Fig. (2): Electronic spectrum of the precursor (Na2L) Fig. (3) 1H NMR spectrum of the ligand (Na2L) IHJPAS Fig .(4): Infrared spectrum of the complex [Co(L)] IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.23 (2) 2010 Fig.(5): Electronic spectrum of the complex [Cu(L)] IHJPAS 2010) 2( 23المجلد مجلة ابن الهیثم للعلوم الصرفة والتطبیقیة المشتقة من نوع قاعدة شیفلیة البایولوجیة للیكاند من عاالفودراسة تخلیق مع األیونات ومعقداته )فنیل األنین-ل( حامض أمیني Co(II), Ni(II), Cu(II) and Zn(II) منهل ریمون عزیز جامعة بغداد ، كلیة التربیة أبن الهیثم ، قسم الكیمیاء خالصةال ل على قاعدة شیفللحصو زالدیهایدهیدروكسي بن-2 مع فنیل األنین -ل الحامض األمیني مفاعلة تضمن البحث Sodium2-(2-hydroxybenzylideneamino)-3-phenylpropanoate التي أستعملت مـادة وسـطیة [NaHL] فتفاعل قاعدة شیأذ أعطى ال داي كلورو أیثان-1,2مع ثم مفاعلتها Sodium2,2'-(2,2'-(ethane-1,2'diylbis(oxy))bis(2,1-phenylene))bis(methan-1-yl-1- ylidene)bis(azan-1-yl-1-ylidene)bis (3-phenyl propanoate) .والتي أستعملت كلیكاند [Na2L] ثم مفاعلة ,M= Co(II), Ni(II) ، [M(L)]تكونـت معقـدات ذوات الصـیغة اذ، بعـض العناصـر الفلزیـة أیونـات یكانـد مـعالل Cu(II), and Zn(II). الكمـي الـدقیق التحلیـلو المرئیـة –االشعة تحت الحمراء واالشعة فوق البنفسـجیة ،ق الطیفیة ائلمركبات بالطر شخصت جمیع ا خص و كـذلك شــ التوصــیلیة الموالریـة الكهربائیــة ومحتـوى الكلــور ودرجـة االنصــهار والحساسـیة المغناطیســیة ، و للعناصـر طة اسااللیكاند بو 1H NMR . السطوح ثماني ي المقترح للمعقدات المحضرةمن نتائج البحث كان الشكل الفراغفأن . Staphylococcusال بكتریا موجبة لصبغة كرام درست الفعالیة البایولوجیة خارج الخلیة الحیة للیكاند ومعقداته ضد aureus وAcinetobacter baumannii ،ر مانع للبكتریا الموجبة لصبغة كرامتأثی أظهرت وجود و. IHJPAS