Microsoft Word - 235-247 IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|235    Synthesis, Spectral and Bacterial Studies of Mixed Ligand Complexes of Schiff Base Derived from Methyldopa and Anthranilic Acid with Some Metal Ions  Lekaa K. abdul karem dr.likaakhalid@gmail.com, orcid.org/0000-0002-0735-128X Taghreed H. Al-Noor drtaghreed2@gmail.com, orcid.org/0000-0002-6761-7131 Dept. of Chemistry/College of Education for Pure Science (Ibn Al-Haitham) /University of Baghdad Abstract Bidentate Schiff base ligand 3-(3,4-Dihydroxy-phenyl)-2-[(4-dimethylamino- benzylidene)-amino]-2-methyl-propionic acid was prepared and characterized by spectroscopic techniques studies and elemental analysis. The Cd(II), Ni(II), Cu(II), Co(II), Cr(III) and Fe(III) of mixed-ligand complexes were structural explicate through  moler conductance, [FT-IR, UV-Vis & AAS], chloride contents, , and magnetic susceptibility measurements. Octahedral geometries have been suggested for all complexes. The Schiff base and its complexes were tested against various bacterial species, two of {gram(G+) and gram(G-)} were shown weak to good activity against all bacteria. Keywords:  Bidentate Schiff Base, Methyldopa, Spectroscopic techniques, and bacterial activities. IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|236    1. Introduction Coordination chemistry that related with the chelate or complexes got a large attention [1-2]. Through chemical bonding as the recent studies the formula which involve of central metal (Lewis acid) and ligands (Lewis base) gives us a strong bond and very stable compounds [3]. Schiff bases form stable complexes with some transition metal ions, and they play an important role in general life with industries such as chemistry and biological activities [4 -6]. Methyldopa, (M-dop) = (α-methyl-3,4-dihydroxyphenyl alanine) is one of the catecholic molecules which are liable to interact with Fe (II). It is a catecholamine used (anti-hypertensive drug) [7]. The stability constants (Ks) of (4 metals) with (Nitrilotriacetic &/ or Iminodiacetic) acids as primary ligands and (Methyldopa and/ or levodopa) as secondary ligands potentiometrically [8]. The spectrophotometric determination of dopamine. HCl and Methyldopa in pharmaceutical preparations using flow injection analysis (FIA). The method is based on oxidative coupling reaction of drug with 2-Furoic acid hydrazide (C5H6N2O2) in the presence of Sodium nitroprusside in (NaOH) medium to form soluble product. The results obtained were in good agreement with those obtained by British Pharmacopoeia method [9]. The stability constants of ternary complexes of M(II) ions with two amini acids (aspartic acid(ASP) &Glutamic (Glu) acid) as primary ligands and (levodopa & Methyldopa )as secondary ligands, also all complexes have been carried out (pH-metrically) [10]. 2. Experimental All chemicals used in this research were purchased from BDH, Fluka and Merck companies and used without moreover purification. The melting points were obtained using "Stuart Melting Point Apparatus". The metal contents of the complexes were obtained by atomic absorption technique using a "Shimadzu AA 620G ". The Chloride contents of complexes were obtained by testing all complexes (0.05 gm.) which were decomposed with conc. Nitric acid and diluted with water. The1H and 13C NMR spectra were performed on by "Brucker DRX system 500 (500 MHz)", University of Tehran. Elemental micro analysis CHNS was carried out by the Euro EA 3000, University of Baghdad. UV-Vis spectra were performed on a "Shimadzu UV- 160A". The FTIR- spectra were carried out by a "Shimadzu, FTIR- 8400S" (4000- 400) cm-1 with samples prepared as KBr discs. Magnetic measurements were recorded on a "Bruker BM6 instrument" at 298K following the Faraday’s method'. Ligand's Preparation (HL [11]) A solution of {4-DMBA} 1 mmole in methanol (10 ml) was added to a solution of {M- Dopa} 1 mmole in methanol (20 ml) and then 1mmol of KOH. The mixture was refluxed for 4~hours with stirring. The product was a deep orange solution. It was allowed to cool and dry at room temperature, then recrystallized with ethanol. The brown colored solid mass formed during refluxing was cooled at room temperature, filtered and washed completely with hot ethanol, and recrystallized from acetone to get a pure sample. It yields 90% . The synthetic pathway is as shown in Scheme -1. IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|237    O HO H3C OH OH N C H N H3C CH3 3-(3,4-Dihydroxy-phenyl)-2-[(4-dimethylamino-benzylidene)-amino]-2-methyl-propionic acid C O H N H3C CH3 + 4-Dimethylamino-benzaldehyde O HO H3C OH OH NH2 Methyl dopa HL ref luxed f or 4~hours Methanol Scheme (1): The preparation of the ligand (HL) Preparation of potassium anthranilate {C7H6NO2K}: potassium anthranilate ligand has been prepared depending on literature method [11]. A general method in preparation of complexes [11]: In methanol solution (2mmol of C7H6NO2K ) and a solution of (HL & KOH) each one is 1mmole were added to a stirred for (1 hour) solution of MClx.nH2O 1mmole. The mixture was (filtered & precipitation) then washed several times with a surplus of ethanol and dried during (24 hours) at room temperature The synthetic pathway is as shown in Scheme -2. IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|238    O HO OH OH N C H N H3C CH3 H2N O O H2N O O O O HO HO N CH N CH2HC M H3C O +K-O H2N 2 Potassium anthralniate + + MCl2.nH2O M= Co(II), Ni(II),Cu(II), and Cd(II) ref lux f or (1 hour) K and H2N O O H2N O O O O HO HO N CH N CH3H3C M H3C M=Cr(III),Fe(III) K HL Methanol Scheme (2): The preparation of complexes 3. Results and Discussion 1. Physical Properties  The physical properties for the starting materials and Schiff base (HL) ligand are given in Table (1a and 1b).  The complexes are soluble in (DMSO) & (DMF), while insoluble in water [12].  The melting points of ligands were lower than all complexes, Table -1c.  The conductivity measurement values in DMSO (10−3Molar) solution range in (31.4-38.1) Ω-1cm2mol-1 for Cd(II) ,Ni(II) ,Cu(II) , and Co(II), complexes. the complexes are electrolytes types 1:1 as the data indicate, but the complexes Cr(III)& Fe(III) were non- electrolytes [13].  Silver nitrate solution was (-) when we exanimated (Chloride ion)  The found and theory values of (M%) in each complex are in good agreement [14]. 2. 1H-NMR spectrum for the ligand (HL) The integral intensities ( δ ) in ppm of each signal in the 1H-NMR spectrum of HL Figure-1, was found to agree with the number of different types of protons present. The signal obtained in range δ (6.44 -7.68) ppm was appointed for doublet due one proton of aromatic ring of phenyl, the formation of Schiff base is supported by the presence of a singlet at (δ 8.46) ppm corresponding to the azomethine proton IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|239    (–N=CH). The signal obtained in range δ (7.10-7.70) ppm was appointed for doublet due one proton of aromatic ring. (m, arom. proton,). The signals observed at δ (1.31 & 1.23) ppm ascribed to methyl protons (-CH3) group4[15,16]. 3. 13C-NMR Spectrum for (HL) The spectrum of [HL] in (DMSO-d6 solvent) is shown in Figure-2. Chemical shift [δ ppm] azomethine H-C=N carbon (C1) at 195ppm. The carbon atoms of aromatic ring at range (δ=130.25-139.24) ppm, note methyl carbon (3CH3) in Schiff base at (δ=41.72 ,41.51 and 41.09) and at δ=40.68 ppm is ascribed to methyl carbon (1CH3) of DMSO [15,16]. 4. FTIR spectra: Methyl dopa spectrum: The bands at (1490) cm-1, (3105) cm-1, (2956, 2808) cm-1 and (1257) cm-1 were appointed to υ(C=C) aromatic, υ(C–H) aromatic, υ(C–H) aliphatic stretching vibration and υ(C–C) aliphatic respectively, Table-2a. The band at (1209) cm-1 which account for υ(C-N) cm-1 stretching vibration. The observed bands at [1618 and 1402 ]cm−1were due to υasym{COO−}carboxyl] and υsym{COO−}carboxyl groups,Δυ{COO-}asym-υ{COO-}sym =216 cm -1.The strong broad bands around (3481 , and 3421 ) cm-1 were ascribed to the stretching vibration of υ (O-H) .The band at (3223) cm-1 was appointed to the stretching vibration of υ (N-H2) [17,18]. Ligand (HL) spectrum: A very strong broad band around (3473) cm-1 ascribed to stretching vibration of (O-H) group, Table-2a and Figure-3. The spectrum shows a new band at (1620) cm-1 ascribed to υ(C=N) str. vibrations of the (HL) with disappearance of the stretching vibration bands for the amine (NH2) group [17]. The bands at (1446) cm -1, (3039) cm-1, (2966) cm-1 and (1273)cm-1 were appointed to υ(C=C) aromatic, υ(C–H) aromatic, υ(C–H) aliphatic and υ(C–C) aliphatic str. vibration, respectively. The observed bands at carboxyl groups] in (HL) respectively [19,20]. A sharp band at (1620) cm−1 was due to stretching vibration of the υ(HC=N-), it was shifted to lower frequency for every complex and its range appeared in (1604–1616) cm-1, indicating coordination of the azomethine N atom (HC=N:→ M ) with the metal ion [ 21] . Anthranilic acid spectrum : the region of all amino acids ( NH3+) appears at (3030- 3130) cm-1 [22], and, the band of AnthH appears at (3101) cm-1, but this band was disappeared in every complex with appearance of coordinated bands NH2 within the range (3062-3371)cm-1, Table-2b. the bands at (1662 & 1485) cm-1 respectively due to υ (COO- )asym and υ (COO -)sym , therefore Δυ = 177 cm -1 , in complexes were shifted to a lower frequency in range (1554-1593)cm-1 for υ (COO-)asym and (1327-1400) cm-1 for υ (COO- )sym, Table-2c . The Δυ = [υ (COO-)asym - υ (COO-)sym] appeared within the range (189- 227) cm-1 indicating that the carboxlate ion coordinates as a mono dentate donor with the metal ions [23]. IR spectra explain that the anthranilato ligand (Anth- ) is negatively charged can be coordinated to the metal atom [M(II) & M(III)] through the nitrogen atom in amin group (H2N→M), and oxygen carboxylate group (-COO _M), serve as a IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|240    bidentate .FT-IR spectral results provide strong evidences for the complexation of Schiff base (HL) with metal ions in bi dentate mode fashion (NO) occured through the [ (O) of carboxylato (-COO-) and (N) of the (HC=N-)] groups. New weak intensity bands were observed in the regions (532-586) cm-1 might be due to M-N and (412-486) cm-1 due to M- O vibrations, [24,25]. The experimental data suggest that the anthranilic acid acts as bidentate uni negative charge and adopt an octahedral geometry as proposed. 5. Electronic spectra and magnetic moment for the ligands and complexes: The UV-Vis spectrum of the ligand (HL), Figure-4, Table-3 shows two peaks at λmax (301 and 344)nm due to (π→ π*) & (n→ π*) transition respectively[26]. The UV- spectrum of (AnthH) showed two high intensity peaks at (242 and 332) nm appointed to (π→ π*) & (n → π*) respectively [22,24]. Cr(III) complex: The (UV- Vis) spectrum, shows high broad peak at 342 nm was indicated to the charge transfer and overlap with υ3 ( 4A2g→ 4T1g(P), while the weak broad peak at 798 nm , which indicated to (4A2g→ 4T2g(F) (d–d), transition in an octahedral geometry , and Magnetic moment value is 3.94 B. M. indicating three unpaired electrons close to spin only value, that agreement of the structure of Cr (III) to be an octahedral geometry Table-3, [26]. [Fe (L)(Anth)2] complex: The electronic spectrum, shows absorption peak in the UV region at 344nm which is ascribed to (CT) transitions while another absorption peak in the visible region at 790 nm which belongs to electronic transition 6A1g→ 4T1g(4P) , Table-3 [26], and μ eff = 5.09 B.M. is lower than the μ eff of the high spin octahedral complex , which is in agreement with an octahedral geometry [27]. [Co(L)(Anth)2] complex: The (UV- Vis) spectrum, shows more than one peak. The first high intense peak at 344nm which is ascribed to (C.T) transitions. The second peak is at 430 nm which is ascribed to 4T1g→ 4T1g(P) υ3 , and the third absorption peaks are of (d-d) transitions as shown in Table-3, at (734 nm) and 790 nm, which are considered as 4T1g→T2g(F) υ1 transitions[28] , and μ eff = 4.36 which suggest an octahedral geometry [24 ]. [Ni (L)(Anth)2] complex: The electronic spectrum shows two peaks at (344nm), which may be appointed to (CT) transitions & (υ3) 3A2g(F)→ 3T1g(P). The peak at 797 nm, which is due to 3A2g(F)→ 3T1g(F) (υ2) {d-d transitions}, respectively [28], and The μ eff = 2.83 B.M. which suggest an octahedral geometry [24]. [Cu (L)(Anth)2] complex: This complex , shows a high intense peak at 344 nm is ascribed to a strong charge transfer and peak at 696nm due to 2Eg →2T2g .These peaks are characteristic in position and width with those reported for octahedral Copper (II) complexes, [28], and μeff = 1.62 B.M. which agrees by several research worker's data[24 ]. [Cd (L)(Anth)2] complex: The diamagnetic properties showed as expected from their electronic configuration of Cd(II) d10 complex which did not display any peak in the visible region. The electronic spectrum of cadimum(II) complex shows the absorption peak at 342nm Table-3 which ascribed to the charge transfer, and which agrees with those complexes that have an octahedral structure [23], and the diamagnetic properties did not show any d-d transition,[24] . IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|241    6. Bacterial activities: Schiff base ligand, Anthranilic acid and the new complexes were tested against various bacterial were given in chart-1. The [Cr(L)(Anth)2] shows negative against E-coli and Bacillus. The [Fe(L)(Anth)2] shows negative result against E-coli and Pseudomonas. Complexes K [Co(L)(Anth2] & K [Ni(L)(Anth2] show good antibacterial activity against the 3-organisms except E-coli. The K[Cu(L)(Anth)2] and K[Cd(L)(Anth)2] show very good antibacterial activity against the four bacteria . Mostly the (ZI)mm of the prepared compounds was in the following order; Metal complexes > AnthH > HL > DMSO K[Cd(L)(Anth)2] > K[Cu(L)(Anth)2] > K [Ni(L)(Anth2] > K [Co(L)(Anth2] >>[Cr(L)(Anth)2] >[Fe(L)(Anth)2] It is obvious from the top datum that the (ZI) increased significantly on celates special the partial sharing of the (M+2 & M+3) positive charge and electronic spectra of d10 of the metal ion with {N and O} atoms as donor groups or increased because of concept of cell permeability the lipid membrane that surround the cell surplus the vocal of only lipid soluble materials pump to which liposolubility is a significant operator that controls antimicrobial activity [29,30]. Table (1a): The physical properties for The starting materials and ligand HL Table (1b): The solubility of the HL in various Solvents (+) soluble & insoluble (–) Compounds Compound formula Molecular weight M .pºC Colour Found (Calc.) C H N O S M-dop C10H13NO4 211.22 290 White 56.86 6.20 6.63 30.30 ------- 4-DMAB C9H11NO 149.19 72-75 White 72.46 7.43 9.39 10.72 ------- HL C19H22N2O4 342.39 160- 165 Brown 64.95 (66.65) 6.87 (6.48) 8.66 (8.18) 13.32 ------- Compound H 2 O D M F D M S O C H 3 O H C 2 H 5 O H C 3 H 6 O C 6 H 6 C C l 4 C H C l 3 Petroleume ether HL - + + + + + - - - - IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|242    Table (1c): Physical Properties of the Mixed [L- Metal-Anth] Complexes Metal% Λm Ω-1 cm2 mol- 1 M .p°c Yield % Colour M. wt Calc. Compound formula theory (exp) 7.81 (6.83) 13.8 250 Dec 80 Brown 665.48 [Cr(L)(Anth)2] C33H33CrN4O8 8.34 (8.70) 9.5 190 89 Brown 669.48 [Fe(L)(Anth)2] C33H33FeN4O8 8.28 (8.24) 31.4 220 67 Brown 711.67 K [Co(L)(Anth)2] C33H33CoK N4O8 8.25 (8.79) 36.2 225 72 Brown 711.43 K [Ni(L)(Anth)2] C33H33N4NiO8 8.87 (9.24) 38.1 240 Dec 78 Brown 716.28 K [Cu(L)(Anth)2] C33H33CuN4O8 14.69 (13.97) 37.9 260 Dec 91 Brown 765.15 K [Cd(L)(A.nth2] C33H33Cd N4O8 M.wt = {Molecular Weight},m={Molar Conductivity},Dec ={decomposition },M .p=melting point Table (2a): FTIR of the M-dop and HL υ(C-H) arom. alph. -CH3 υ (C- N) υ(C=C) arom. Alph. (COO) υ asy υ sym HL υ(C=N-) υ (N-H2) υ (OH) arom compounds 3015 2956,2808 1375 1209 1490 1257 1618 1402 -------- 3223s 3481 3421br M-dop 3039 2966 1315 1249 1449 1273 1593 1365 1620 -------- 3473 HL Table (2b): FT-IR of the L-Anthranilic acid Δ (-COO-)asmy- smy (-COO-)sym. (-COO -)asym. C=O Str (carbox.)  (N-H3 +) (NH2) asym,sym Str 177 1485s 1662s 1716 3101s 3321 s 3240 IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|243    Table (2c): FT-IR of the complexes Table (3): Electronic spectral of the mixed [L- Metal-Anth] Complexes Comp. λmax nm υ' cm-1 Є max Mol-1.L.cm-1 Assignments µeff B.M [Cr(L)(Anth)2] 342 798 29239 12531 2444 13 Charge transfer 4A2g→ 4T1g(P) ν3 3.94 [Fe(L)(Anth)2] 344 790 29069 12658 1797 41 Charge transfer 6A1g→ 4T1g(4P) υ3 5.09 K [Co( (Anth2] 344 430 734 790 29069 23255 13623 12658 1691 70 54 Charge transfer 4T1g→ 4T1g(p) υ3 4T1g→ 4T2g(F) υ1 4.36 K [Ni(L)(Anth2] 344 797 29069 12547 1700 16 C.T 3A2g(F) → 3T1g(p) υ3 2.83 K[Cu(L)(Anth)2] 344 696 29069 14367 1712 55 Charge transfer 2Eg →2T2g 1.62 K[Cd(L)(Anth)2] 342 29239 1874 C.T Diamagnetic υ (M-O) for L3&(Anth ) υ (M-N) for L3&(Anth ) Δ υ (- COO ) asym- sym (-COO) asy,sy m υ C=C arom υ(HC=N -) υ (C– H) +CH3 aliph. υ (NH) asy,sy m in Anth υ (OH) arom Comp. 459 414 568 540 212 1577 1365s 1523 1612 2943 2816 3371 3078 3444 [Cr(L)(Anth)2] 462 412 567 532 208 1581 1373 1523 1612 2981m 2816 3363 3062 3479v s [Fe(L)(Anth)2] 455 416 586 563 207 1593 1386 1535 1612 2939 2812 3305 3136 3433 K [Co( (Anth2] 466 412 567 532 202 1593 1381 1543 1604 2943 2804 3305 3217 3429 K [Ni(L)(Anth2] 462 424 563 536 227 1554 1327 1527 1604 2947 2808 3275 3236 3433 K[Cu(L)(Anth)2 ] 451 412 578 555 189 1589 1400 1535 s 1616 2939 2804 3290 3136 3433 K[Cd(L)(Anth)2 ] IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|244    Figure (1): 1H-NMR spectrum of the ligand (HL) Figure (2): 13C-NMR spectrum of the ligand (HL) Figure (3): FT-IR of (HL) IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|245    Figure (4): Electronic spectrum of the (HL) Figure (5): The (ZI) of mixed [ L-Metal -Anth] complexes References [1] S. Annapoorani and C. Krishnan ,Synthesis and spectroscopic studies of trinuclear N4 Schiff base complexes international, J. ChemTech Res., 5 (1): 180–185. 2013 [2] D.Chen and A.E Martell, Dioxygen affinities of synthetic cobalt Schiff base complexes. Inorganic Chemistry, 26, 1026-1987. 1987 [3] F.Tehmina ; F. Nasreen; Zafar Abbas Zaidi1, Tanveer Abbas , Mohib R. Kazimi; Investigation of Iron Complex Formation of Anti-Hypertensive Drug: Methyldopa, American Journal of Analytical Chemistry, 6(6): 551. 2015 [4] S. Kumar; S. M. Lim; K. Ramasamy,  Synthesis, molecular docking and biological evaluation of bis-pyrimidine Schif base derivatives, Kumar et al. Chemistry Central Journal 11:89. 2017 [5] Atmaram. K. Mapari1 and Kiran. V. Mangaonkar; Synthesis, Characterization and Antimicrobial Activity of Mixed Schiff Base Ligand Complexes of Transition Metal(II) ions,  International Journal of ChemTech Research, 3(1):477-482. 2013 [6 ] AB. Patil; Stability Constants of Ternery Complexes of Transition Metal (II) ions with Aspartic Acid and Glutamic Acid as Primary Ligands and Levodopa and Methyldopa  as Secondary Ligands , Oriental J. Chem., 28, (3): 1321-1324. 2012 0 5 10 15 20 25 30 35 40 45 E‐coli  Pseudomonas Staphylococcus aureus Bacillus    IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|246    [7] "Who Model List of Essential Medicines''. World Health Organized. October (2013) Retrieved 22 April 2014(2013) . [8] A. B.Patil and T. H. Mhaske. , "  Potentiometric Studies on Binary and Ternary Complexes of Transition Metal Ions with Some Pharmaceutical Compounds"Asian J. Chem., 13(4): 1544-1548 . 2001 [9] M. Q. Al-Abachi, Raghad Sinan and Hind Haddi .," Spectrophotometric determination of methyldopa and dopamine hydrochloride in pharmaceutical preparations using flow injection analysis" , National Journal of Chemistry, 36 : 597-604. 2009 [10]  L. K. Abdul Karem T. H. Al-Noor and F. M. Ali ; Schiff Base And Ligand Metal Complexes of Some Amino Acids and Drug, LAMBERT Academic Publishing Germany, March, 2016 . [11] T. H. Al-Noor ; Amer. J. Jarad and A. O. Hussein ;  Synthetic, Spectroscopic And Antibacterial Studies Of Fe(II),Co(II),Ni(II),Cu(II),Zn(II),Cd(II)and Hg (II),Mixed Ligand Complexes Of Saccharin And Amoxicillin(antibiotics), Chemistry and Materials Research, 6(3):20-30. 2014 [12] G. Omoruyi; Idemudia1, A.Peter; Ajibade1 and Anthony I. Okoh;  Synthesis, characterization and antibacterial screening of 2, 4-diaminopyrimidine pyrimethamine and trimethoprim silver complexes, African Journal of Biotechnology .,  11(39): 9323-9329. 2012 [13] W. J.Geary ; The Use of Conductivity Measurements in Organic Solvents for the Characterization of Coordination Compounds Coord, Chem. Rev., 7: 81-122. 1971 [14] V. AIA ; Text Book of Quantitative Inorganic Analysis , 2nd Ed (Longman, London),: 694. 1978 [15] WW. Simons ; The Sadtler Handbook of Proton NMR Spectra, Sadtler Re-search Laboratories , Philadelphia, Sadtlerk,1978. [16] Y. Sakakibara; S. Okutsu; T. Enokida; T. Tani; Red organic electroluminescence devices with a reduced porphyrin compound, etraphenylchlorin . Applied Physics Letters, 74(18)(199): 2587. [17] K. Nakamoto ,Infrared and Raman Spectra of Inorganic and Coordination Compounds, 3th Ed., John Wiely and Sons, New York. 1986. [18] R.M. Silverstein, and F.X. Webster; Spectrometric Identification of Organic Compounds, 6th Ed .New York , John Wiley and Sons ,Inc,:401-406. 1996 [19] T. H. Al-Noor , A. J. Jarad and A. O. Hussein ; Synthesis, Physico-Chemical and Antimicrobial Properties of Some Metal (II)-Mixed Ligand Complexes of Tridentate Schiff Base Derives From Β-Lactam antibiotic {(cephalexin mono hydrate)-4- chlorobenzophenone} and saccharin , International Journal of Chemical and Process Engineering Research, 1(11): 109-120. 2014 [20] A. L.Davis; J. Keeler; E. D. Laue, , & D. Moskau,; Experiments for recording pure- absorption heteronuclear correlation spectra using pulsed field gradients, Journal of Magnetic Resonance (1969), 98(1): 207-216. 1992 [21] K. Nakamoto, "Infrared Spectra Of Inorganic And Coordination Compounds "4 th ED ;John. Wiley and Sons, New York. 1996. [22] T.H. Al-Noor and L.K. Abdul Karem;  synthetic, spectroscopic and antibacterial studies of Co(II),Ni(II),Cu(II),Zn(II),Cd(II)and Hg (II),mixed ligand complexes of trimethoprime antibiotic and anthranilic acid ,TOFIQ Journal of Medical Sciences, 3 (2): 64-75. 2016 [23] T.H.AL-Noor and L.K. Abdul Karem ; Synthesis , Characterization and Antibacterial Activities of Co (II),Ni(II),Cu(II),Zn(II),Cd(II)and Hg(II) Mixed-Ligand Complexes of L- Proline and Trimethoprim antibiotic ,Chemistry and Materials Research, 7 (3), 32-39. 2015 IHSCICONF 2017 Special Issue Ibn Al-Haitham Journal for Pure and Applied science https://doi.org/ 10.30526/2017.IHSCICONF.1797 For more information about the Conference please visit the websites: http://www.ihsciconf.org/conf/   www.ihsciconf.org   Chemistry|247    [24] C. J. Brown; The Crystal Structure of Anthranilic Acid, Proc. Royal Society of London A, 302: 185-199. 1968 [25] S.H. Naji, L.K. Abdul Karem and F. H. Mousa; Synthesis, Spectroscopic and Biological Studies of a New Some Complexes with N-Pyridin-2-Ylmethyl-Benzene-1,2- Diamine, Ibn Al-Haitham Jour. for Pure & Appl. Sci.26(1):194-207. 2013 [26] Lever ABP Inorganic Electronic Spectroscopy (2nd ed.). Elsevier. in Amsterdam, New York. 1984. [27]Cosmetic Ingredient Review Expert Panel ;Final report of the safety assessment of niacinamide and niacin".Int. J. Toxicol,24 (5): 1–31. 2005 [28] T.H. Al-Noor and L.K. Abdul Karem ;  Synthesis, Physico-Chemical and Antimicrobial Activities Co(II),Ni (II) ,Cu(II), Zn(II),Cd(II) and Hg(II) Mixed Ligand Complexes of L- Alanine and Trimethoprim Antibiotic, Chemistry and Materials Research , 7 (5):82-90. 2015 [29] M.N. Patel; V.J.Patel;  Studies on Novel Coordination Polymers of a Tetradentate Ligand with Some Transition Metal Ions, Synth .React. Inorg. Met. Org. Chem.: 19: 137. 1989 [30] K. P. Srivastava; Sunil Kumar Singh and Bir Prakash Mishra; L-1β, IL-1Ra and IL- 18 gene variants in type 2 diabetes, Journal of Chemical and Pharmaceutical Research, 7(1):197-203. 2015