Synthesis and Characterization of New Metal Complexes of -Amminonitriles Derived from P- Methoxybenzaldehyde with Aromatic 2002( 22مجلة ابن الهيثم للعلوم الصرفة والتطبيقية المجلد ) تحضير وتشخيص معقدات فلزية جديدة أللفا أمينونتريل مشتقة من بارا ميثوكسي بنزالديهايد مع األمينات األروماتية رواء عباس مجيد جامعة بغداد ،كلية الزراعة ،شعبة العلوم األساسية الخالصة مررر [Cu(II), Ni(II),Co(II), Fe(III)]عقررر ف ية جرررة ل جررر و ارررلعن صج ارررق فاعاق ررر ف ا ققاجرررة مضررر ح مجث كارف صاجةجار – )لرق ف HLIIلرق ف مجث كارف ياجر فارج ا ج -مثجر فاجةجار -= )لرق ف HLIفاةجكقا جن فامحضر جن ارقلقق ار جن –مجث كارف لا فا جاقجر مر لرق ف - جقة ار جك لماقلةرة لرق فلق ف مجث كاف ياج فاج ا ج . حض فاةجكقا فن لط– صااررج جن لةررت فا رر فاف. را رر فكجرر فامعقرر ف فااة جررة فال جرر و ل اررقطة ف م ررقن فارر فاةالررف يضرر لررن - لررق ف ا جةجة فاكا لقئجرة فام ئجة. ح فجضق فاا قئن فامغاقطجاجة ف -صطجقف فألرعة ح فاحم فء فألرعة ي ق فالااالجة اةمعق ف فااة جة، كقن اة ك فاةجكقا ف ثاقئجة فاان ج لطقن لقألج اق فااة جة لن ط جق ف فاا لجن DMFيف م ج Ni(II)فحرق فاارن لق لقطرر مر صجرر ن قاررة ك HLIIاررةك فاةجكقار C6لر ف فامعقر فمجارر ملم لرة فاا جرر -املم لرة فاارق ا ج يقط .لن ط جق ملم لة فا IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 Synthesis and Characterization of New Metal Complexes of -Aminonitriles Derived from P- Methoxybenzaldehyde with Aromatic Amines R. A. Majeed Divison of Basic Sciences College of Agriculture, University of Baghdad . Abstract New metal complexes of some transition metal ions [Fe(III) , Co(II) , Ni(II) and Cu(II)] of two previously prepared ligands HLI=(P-methyl anilino)- P-methoxy phenyl acetonitrile and HLII =(P-methoxy anilino)-P- methoxy phenyl acetonitrile were synthesized. The two ligands were prepared by Strecker's procedure which included the reaction of P- methoxybenzaldehyde with p-toluidine and P-anisidine respectively. The structures of the new metal complexes were characterized by atomic absorption , i.r and U.V.-visible spectra . Magnetic susceptibilities and conductivity measurements in DMF of metal complexes were also studied. These ligands coordinate as abidentate molecules through nitrogen atoms of - amino group and nitrile group except the complex C6 of the ligand HLII coordinates as monodentate with Ni(II) ion through nitrile group only. Introduction The chemistry of nitrile and -aminonitrile compounds and their derivatives has received special attention because of their application as potential ligands for a large number of metal ions (1-5). Strecker was the first to prepare -amino nitriles for treating aldehydes or ketones by their treatment of alkaline cyanide and salts of amines (6). The ligands (HLI and HLII) previously prepared were synthesized by a modified Strecker's procedure (7). Nitriles and -aminonitrile derivatives had a biological activities (8,9) as herbicides (10) , pharmacological agents (11) and biological synthesis of chemical compounds by it’s microbial metabolism in some organisms (12). Complexes containing more than ametal centre represent the synthetic models of ferromagnetic interaction between the metal centers which can explain oxidation- reduction processes in biological systems in addition to their catalytic and biological activities (13-16). Beside that, some aminonitriles were used to prepare racemic compounds (17) . In this work the synthesis and the characterization of new metal complexes of some transition metal ions [Fe(III), Co(II), Ni(II) and Cu(II)] of HLI(P-methyl anilino)- P-methoxy phenyl aceto nitrile and HLII (P-methoxy anilino) –p- methoxy phenyl aceto nitrile are studied . Coordination behaviour of ligands with metal ions were investigated The structural formula of two ligands are illustrated in scheme(1). R= CH3 in HLI with M=Ni(II), Co(II) and Fe(III); = OCH3 in HLII with M=Cu(II), Fe(III) and Ni(II). Scheme(1):-aminonitriles derived from P- methoxy benzaldehyde with aromatic amines. R NH CH C N OCH3 IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 Experimental Apparatus Melting points (uncorrected) were obtained by using Gallenkamp MF-600-010F melting point apparatus. Infrared spectra of metal complexes were recorded as CsI discs on Perkin- Elmer 1310R. Spectrophotometer. Electronic spectra of two ligands and their complexes in DMF were recorded on U.V.-visible spectrophotometer Shimadzu U.V.-160A. Electrical conductivities of metal complexes, in DMF (10 -3 M) were measured at room temperature by using Hunts Capacitors Trade Mark (British) . Magnetic susceptibility (μeff B.M) of metal complexes were measured at room temperature by Faraday method using Balance, magnetic susceptibility, model MSB-Mk-1. Determination of metal content (%) of complexes were carried out by using Varian-AA775, Atomic Absorption spectrophotometer and Perkin-Elmer 5000 Atomic absorption spectrophotometer. Materials and Methods Metal salts Fe (NO3)3. 9H2O 99.9%, Co(NO3)2. 6H2O 99% (Fluka); Ni(NO3)2. 6H2O 99.9%, Cu(NO3)2.3H2O 99% (Merck) ethanol absolute 99% (Fluka) were used as received from the suppliers. Dimethyl formamide (DMF) was dried and distilled prior to use (18) . Preparation of -aminonitriles (HLI and HLII) : The aldehyde p-methoxy benzaldehyde 0.05 mole was dissolved in 50 ml of glacial acetic acid , (p-toludine , p-anisidine) sulfonic acid was added in small portions to bring the pH to 2 , followed by the additions of 0.05 mole of the amine. The pH was adjusted to 3-4 by adding concentrated H2SO4 drop wise . KSCN 0.05 mole was added to the mixture which was kept stirring . The end of the reaction was checked by the disappearance of the starting material (the amine) and development of a higher spot on T.L.C . The reaction mixture was poured on ice and made slightly alkaline with ammonia . The solid product was filtered , washed with water and dried . Preparation of metal complexes of HLI (C1 of Ni(II) , C2 of Co(II) and C3 of Fe(III)) and HLII (C4 of Cu(II) , C5 of Fe(III) and C6 of Ni(II)): A solution of a metal salt of Fe(III), Co(II), Ni(II) and Cu(II) in absolute ethanol was added to ethanolic solution of the ligand with a continuous stirring. The molar ratio of the reactants was 1:2 in C1 , C2 and C6 , 1:1 in C3 and 2:2 in C4 and C5. Precipitation of C4 and C5 took place immediately, while precipitation of other complexes required heating under reflux for 30-60min. The products were filtered off , washed several times with ethanol and dried under vacuum. Results and Discussions a) Physical data and atomic absorption : Table (1) describes the physical properties of metal complexes of HLI and HLII. The suggested molecular formula were further supported by spectral studies. Atomic absorption of few complexes showed less agreeable results because of technical errors in the instrument. All the complexes were insoluble in water , methanol and ethanol .The complexes are however , soluble in DMF and chloroform. b) Infrared spectra: Important characteristic stretching frequencies of the ligands and their metal complexes are described in Table (2) and their spectra are shown in figure(1). The i.r spectrum of complexes C2, C3 and C5 showed shifts in position of C≡N band (19,20) this band is increased in complex C3 and C5 from free ligand. This refers to C≡N coordination to metal ion via-σ donation of the lone pair of electrons of nitrile nitrogen atom (19). The spectra of complex C2 showed decreases of C≡ N , the decreases were attributed to metal d to ligand P * back- bonding (1,2,20). In complexes C1, C4 and C6 showed the bands of C≡ N splitting which refers to coordination of metal ion to nitrogen atom (2,20). The FTIR spectra of complexes C1 and IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 C2 exhibited the N-H and N-H (1500-1516)cm -1 shifted to lower frequencies from free ligand while those of compared with the C3, C4 and C5 showed the disappearance of the N-H and N-H . These changes which refer to coordination of α-amino nitrogen to the metal ion (15,20). The complex C6 exhibited achange of N-H to ahigher frequency. This is attributed to the absence of both hydrogen bonding and coordination with Ni(II) ion (21). The bands appeared at (3321-2970) and (2960-2843) cm -1 were assigned to aromatic and aliphatic C-H respectively (22). The bands related to aromatic C=C vibration appeared at (1603-1612) cm -1 (23) . The bands related to C-O, CH3, and C-C vibrations appeared at (1078-1015) , (1306-1466), (1182-1173) and (966-934)cm -1 respectively (22,23,24). Nitrate ions exhibited vibration modes related to ionic behaviours in complexes C1,C2, C3,C4 and C6 , while bidentate bonding in C3 and C5 and monodentate in C5 (21,23) . Vibration modes of lattice and coordinated water were observed in spectra of C3, C4, C5 and C6 (21,25). New bands appeared at lower frequencies were assigned to M-N≡C, M-N and M-O stretching modes (21,23,26). From the above spectra, it is concluded that the ligands HLI and HLII act as bidentate ligand coordinating through the nitrogen atoms of the α-amino group and the nitrile group, This is in the case of C1, C2, C3, C4, and C5 complexes, but in the case of C6 complex the ligand would coordinate through the nitrogen atom of nitrile group with Ni (II) ion. C) Electronic spectra, Magnetic susceptibility and conductivity measurements: The electronic spectra of the prepared -aminonitrile showed main band observed in the u.v region and was assigned to →* transition of the aromatic rings and CN group and other conjugated system (24). The spectrum of HLII showed low intensity band observed at (27419)cm -1 was assigned to n→* transition may be masked by →* band .Table (3) describes bands of maximum absorption of ligands and their metal complexes in DMF with their assignments together with crystal field parameters (Dq/B`, B` , 10Dq and ) . The latters were determined by applying band ratios on Tanabe Saugano diagrams of specified metal ion (27-29). The absorption bands of ligands and their metal complexes are shown in figure (2). Complexcation with metal ion caused shifts of ligand bands to lower wave numbers and the appearance of new bands in the visible and near i.r. regions. These additional bands may be related to M-L charge transfer bands and ligand field (d-d) transitions (27-29). Ni (II) complexes C1 and C6: The complex C1 was found diamagnetic which refered to a square planar geometry (23,30). The spectrum of these complex in DMF showed two bands attributed to a square planar Ni(II) transitions (23,27,30,31). The spectrum of the complex C6 exhibited two bands were attributed to octahedral Ni(II) complexes (27,28) . The band appeared at (27274)cm -1 was due to (C.T) transition (27-29). By applying band energies and ratio υ2/υ1 (1.44) on Tanabe Saugana diagram, the energy of 10Dq and υ3 was calculated from diagram and the results are given in table (3) . The value of β indicated covalent character (28) . Magnetic moment of the complex C6 was 3.78 B.M came in an agreement with those of octahedral geometry (15,23,25,27) . Co (II) complex C2: Magnetic moments (eff =3.81B.M) of Co(II) complex referred to a tetrahedral geometry (32). The spectrum of this complex in DMF exhibited a single band at (10256)cm -1 was assigned to (2) and multiplet of three bands appeared at (15000, 17046 and 19231)cm -1 and the average value of muliplet (17092)cm -1 was assigned to (3). The position of the absent band (1) was calculated by applying band ratios and energies of absorptions band on Tanabe Saugano diagrams (27-29). The transitions of these bands are given in table (3) of tetrahedral Co(II) geometry (27-29) the value of β indicates a covalent character (27,28) . Band observed in complex was referred mainly to ligand →metal charge transfer (28). Fe (III) complexes C3 and C5: Magnetic moments of C3 and C5 were 5.57 and 3.89BM respectively. Magnetic moment of C5 is lower expected due to the presence of antiferromagnetic interaction of the dimeric IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 octahedral Fe(III) complexes (16,25,28). Low intensity bands were observed in the spectra of the two complexes were attributed to the forbidden transition which was the characteristic of d 5 octahedral complexes (27-29). The band at (23077) cm -1 in C3 was assigned to LM(C.T) transition (27-29). Cu (II) complex C4: Magnetic moments of the complex C4 (eff =1.89 B.M) suggests that the unpaired spins of two copper atoms are coupled through conjugated ligand bridge. The spectra of the complex showed that three bands were attributed to spin allowed the transitions of Jahn Teller tetragonally distorted octahedral Cu(II) complexes (15,26-28) . Conductivity measurements of complexes C1, C2, C3,C4, and C6 in DMF (10 -3 M) showed that they were electrolytes with ionic ratio of 1:2 in C1 C2, C4 and C6 and 1:1 in C3 while C5 was found to be non electrolytic (33). References 1.Nlbertin , G.A.; Antoniutti, S.; Lanfrnchi, M.; Pelizzi, G. and Bordignon, E. (1986) Inorg. Chem, 25,950-957. 2.Clarke , R.E. and Ford , P.C. (1970) . Inorganic chemistry 9,2, 227-233. 3.Bancroft ,G.M.; Mays, M.J.; Prater , B.E. and Stefanini, F.P. (1970), J. Chem. Soc. (A), 2146-2149. 4.Tranchier , J.P.; Chavignon , R.; Prim , D.; Auffrant , A.; Plyta , Z.; Rose Munch F. and Rose ,E. (2000) , Tetrahedron Letters , 41 , Issue 19 , 3607-3610 . 5.Enders D.; and Shilvock, J.P. (2000) , Chem. Soc Rev, 29, 359-373. 6.a) Harusawa,S.; Hamada ‘Y. and Saioiri,T. (1979) Tetrahedron Letters, 48,4663-4666.; b) ogata ,Y. and Kawasaki, A. (1971) , J.Chem. Soc. (B), 4, 325-329. 7. Kh. A. Al-Timeemey, M.Sc. thesis, Baghdad University, 2000, and References cited therein. 8.Weeb ,L.J. and Boxer, S. G.; (2008) , Biochemistry, 47,1588-1598. 9.a) Liu,G.; (2003), Nuclear Medicine and Biology, 29, lssue1, 107-113; b) Cameron, L.M.; Lafrance, R.J.; Hemens ,C.M. and Rajaraman, K.; (1985) , Anti-cancer Drug 1,1, 27-36 (Eng). C.F. C.A. 104 (1986) 102055e. 10.Helga, S.; woldemer,W.; Juergen, H.; Kramer and wilfried, (1985) , Ger. (East). DD 223,624 (Cl.101N57/20), 19 Jun (1985) appl, 256,649, 14 Nov (1983); 8pp.C.F. C.A. 104 (1986) P16541d. 11.kalir,A.; Ederey, H.; Pelah,Z.; Baldormon D. and Porath,G.; (1969), med., J. Chem., 12,474-478. 12.Wyatt J.M and Linton, E.A.; (2007), " Cyanide Compounds. In Biology" . John wiely, Inter science online Book. 13.a) Meyer , F.; H-kryspin , I.; Kaifer , E. and Kircher , P.; (2000) , European Journal of Inorganic Chemistry ,Issue 4 , 771-781 . b) Incarvito , C.; AL. Rheingold , AL. Gavrilova , Qin ,C. and and Bosnich ,B. (2001) , Inorg. Chem. , 40 , 17 , 4101-8 . 14.patel, K.V.; Bhattacharya, P.K.; (1986), Polyhedron, 5,3,731-734. 15.M. Shakir , A. Mohamed , S.P. Varleey and O.S. Nasman , (1996) , Indian Journal of Chemistry , 35A,935-939 . 16.Saha , M.K.; Dey , D.K.; Choudhury , C.R.; Dey ,S.K.; Mitra , S. and Lehmann , C.W.; (2003) , Chemistry Letters , 32 , 12 , 1136 . 17.Beaufort – Droal ,V.; Pereira , E.; Thery V. and Aitken , D.J.; (2006) , Tetrahedron , 62 , Issue 51 , 11498-11954. 18.Vogel, A. (1972) , " Text Book of Practical organic chemistry" 3 rd . Edn Logman 167-69. 19.Getahun, Z.; Huang,C-Y.; Wang, T.; Deleon, B.; DeGrado ,W.F. and Gai, F.; (2003), J.Am.chem. Soc, 125, 405-411. 20.Refat , M.S. and Sadeek , S.A .; (2006) , Canadian Journal of Analytical Sciences and Spectroscopy , 51 , 6 , 312-322 . IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 21.Nakamoto K., (1997)., " Infrared and Raman Spectra of Inorganic and coordination compounds " 5 th Edu. John wiely and Sons, Inc. New York. 22.Dyer,R.; (1965), " Applications of Absorption Spectroscopy of organic compounds" , Prentic-Hall , Inc., Englewood cliffs, N.J. London. 23.Campbell, M.J.; Card D.W. and Grzeskowiak, R. ; (1970) , J. Chem.. Soc. (A), 672-675. 24.Silverstein R.M.; Bassler, C.G.; Morril, T.C., (1974) , " Spectrometric Identification of Organic Compounds " , 3rd. Edn., John wiely and Sons Inc. New York . 25.Burger, K.; (1967) " Coordination Chemistry: Experimental Methods" , London, Butter worth. 26.Lever , A.B.P. and Ramawamy , B.S.; (1973) , Can. J. Chem. , 51 , 514-519 . 27.Lever, A.B. P.; (1984) , " Inorganic Electronic Spectroscopy" , Elsevier publishing company, Amsterdam, London, New York. 28Figgis, B.N.; (1966) , " Introduction to Ligand Fields " Interscience Division of John wiely and sons New York. 29.Sutton, D.; (1968) , " Electronic Spectra of Transition Metal Complexes " 1st Edn Mc Graw-Hill. Publishing Company LTD., London. New York. 30.H.Reeddy, K.; Reddy , M.R. and Lingappa, Y., (1996) , Indian Journal of Chemistry, 35A , 775-778. 31.El-Halabi , N.M. and Awadallah , A.M.; (2005) , Journal of the Islamic University of Gaza , 13 , 2 , 85-90 . 32.Jenkins , D.M.; Di Bilio , A.J.; Allen , M.J.; Betly , T.A. and Peters , J.C. ; (2002) , J.Am.Chem.Soc. , 124 , 51 , 15336-15350 . 33.Gearg ,W.J ; (1971) , Coordination Chem. , Revie , 7 , 81 . According to these observations and data obtaind from atomic absorption and i.r spectra the structures of complexes were suggested as illustrated . C2: [Co(HLI)2].(NO3)2 C1: [Ni(HLI)2].(NO3)2 IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 C4: [Cu2(LII)2(H2O)8].(NO3 )2 IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 Table (1): Molecular formula physical properties and atomic absorption of metal complexes for HLI and HLII and their names Symbol Molecular formula (colour) Names m.p˚C Yield% M% Found (calc.) HLI C16H16N2O (Yellow) (p-methyl anilino)-p-methoxy phenyl acetonitrile 95-96 70 - C1 [Ni(HLI)2](NO3)2 (greenish yellow) [bis{(p-methyl anilino)-p-methoxy phenyl acetonitrile} nickel (II)] nitrate 250-252 55 9.11 (8.55) C2 [Co(HLI)2](NO3)2 Yellow [bis{(p-methyl anilino)-p-methoxy phenyl acetonitrile} cobalt (II)] nitrate 248 Decomp. 50 8.11 (8.58) C3 [FeLINO3(H2O)2].NO3.2.2 H2o (dark brown) [Nitrato-diaqua{(p-methyl anilino)-p- methoxy phenyl aceto nitrile} ferric (III)] nitrate. (2.2) Hydrate 230 Decomp. 45 11.04 (11.02) HLII C16H16N2O2 (brown) (p-methoxy anilino)-p-methoxy phenyl acetonitrile 103-104 60 - C4 [Cu2(LII)2(H2O)8](NO3)2 (dark brown) [Octaaqua-di--{(p-methoxy anilino)- p-methoxy phenyl acetonitrile} dicopper(II)] nitrate < 270 42 13.42 (13.67) C5 [Fe2(LII)2(NO3)4(H2O)2]. 5H2O (dark brown) [Tetra -nitrato-diaqua-di--{(p- methoxy anilino)-p-methoxy phenyl acetonitrile} diferric(III)] (5) Hydrate < 270 33 10.42 (10.93) C6 [Ni (HLII)2 (H2O)4](NO3)2.0.2 H2O (greenish brown) [Tetraaquabis{(p-methoxy anilino)-p- methoxy phenyl acetonitrile} nickel (II)] nitrate. (0.2) Hydrate 240-242 59 10.73 (10.68) Table (2): Characterterstic Stretching vibrations  (cm -1 ) of i.r. spectra for ligands and their metal complexes Symbol N-H  C N H2O Lattice (coordinate)  M-NC M-N M-O NO3 -CH out of plane HL1 3360 2220 - - - - - 840 740 700 C1 Ni(II) 3230 2400 2164 - 446 (295) b - 1750 - e 1645 833 C2 Co(II) 3352 2172 - 412 (289) b - 1750- e 1660 870 785 750 C3 Fe(III) - 2430 3414 (694) 428 (356) a (316) c (298) d (1670) e 1415 g 1364 785 725 775 HLII 3320 2220 - - - - - 840 790 740 C4 Cu(II) - 2300 2137 (650) (600) 467 (353) a (320) c 1750 e 1650 839 745 700 C5 Fe(III) - 2370 3454 (704) 467 (357) a (312) c (285) d (1512) f 1366 g 1312 830 780 700 C6 Ni(II) 3422 2200 2168 3500 650 615 448 - 390 c 353 (1750) e 833 756 Where : a = M-N, b=M-NH , C = M-OH2 d=M-ONO2, e=Free ion NO - 3 , f = monodentate of NO - 3, g =bidentate of NO - 3 Table (3): Electronic spectral data, electrical conductivities (DMF 10 -3 M), Magnetic susceptibilities (effB.M) and suggested geometries for metal complexes of HLI and HLII symbol Maximum absorption υmax (cm -1 ) Band assignment Dq/B` B` cm - 1  10Dq υ2/υ1 Molar conductivity in DMF S. mol -1 cm 2 eff B.M Suggested structure HLI 31447   * - - - - - - - - C1 Ni(II) υ 1 14286 υ 2 18750 1 A1g  1 A2g 1 A1g  1 B1g - 165 Diamagnetic Square planar C2 Co(II) υ 1 6266 (cal.) υ 2 10256 υ 3 17092(avr) υ 4 27777 4 A2  4 T2(F) 4 A2  4 T1(F) 4 A2  4 T1(P) L  M (C.T) 1.1 570 0.587 6270 1.64 145 3.81 Tetrahedral C3 Fe(III) υ 1 15974 υ 2 18750 υ 3 23077 υ 4 26366 υ 5 28000 6 S(A1g)  4 G ( 4 T2g) 6 A1g  4 T1g L  M (C.T)   *   * - - - - - 57 5.57 Octahedral HLII υ 1 27419 υ 2 32075 n  *   * - - - - - - - - C4 Cu(II) υ 1 12376 υ 2 15385 υ 3 18181 2 B1g  2 A1g 2 B1g  2 B2g 2 B1g  2 Eg - - - - - 170 1.89 Octahedral C5 Fe(III) υ 1 10072 υ 2 18868 6 S( 6 A1g)  4 G ( 4 T2g) 6 A1g  4 T1g - - - - - 30 3.89 Octahedral C6 Ni(II) υ 1 10256 υ 2 14815 υ 3 23333 (cal.) υ4 27274 3 A2g  3 T2 g(F) 3 A2g  3 T1g (F) 3 A2g  3 T1g (P) L  M (C.T) 2.06 4.92 0.48 10135 1.44 174 3.78 Octahedral C.T intraligand IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 Fig. (1) : I.R spectra of HLI and HLII IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 Fig. (1) : continued FTIR Spectra of HLI complexes C1:Ni(II), C2:Co(II) and C3:Fe(III) C1 C2 C3 IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 FTIR Spectra of HLII complexes C4:Cu(II), C5:Fe(III) and C6:Ni(II). Fig. (2): Electronic Spectra of HLI and HLII and their metal complexes C1:Ni(II), C2:Co(II), C3:Fe(III), C4:Cu(II), C5:Fe(III) and C6:Ni(II), Fig. (1) : continued C6 C4 C5 IBN AL- HAITHAM J. FOR PURE & APPL. SCI VOL.22 (2) 2009 Fig. (2): Electronic Spectra of HLI and HLII and their metal complexes C1:Ni(II), C2:Co(II), C3:Fe(III), C4:Cu(II), C5:Fe(III) and C6:Ni(II), Fig. (2): Electronic Spectra of HLI and HLII and their metal complexes C1:Ni(II), C2:Co(II), C3:Fe(III), C4:Cu(II), C5:Fe(III) and C6:Ni(II), HLI HLII C5 C2 C6 C3 C1 C4