Research Journal of Recent Sciences _________________________________________________ ISSN 2277-2502 Vol. 1(11), 9-15, November (2012) Res.J.Recent Sci. International Science Congress Association 9 Synthesize, Characterization and Thermal behavior of some New Mercury and Cadmium halides Coordination compounds of Recently synthesized Schiff base Montazerozohori Morteza1*, Musavi Sayed Ali Reza and Joohari ShivaDepartment of chemistry, Yasouj University, Yasouj 7591874831 IRAN Department of Basic Science, Yasouj Branch, Islamic Azad University, Yasouj, IRANAvailable online at: www.isca.in Received 14th May 2012, revised 27th May 2012, accepted 30th May 2012Abstract Some new cadmium (II) and mercury (II) halides complexes of the bidentate Schiff base ligand N,N-bis [(E)-3-(2-nitrophenyl)allylidene)]benzene-1,2-diamine (L) were synthesized, and characterized by physical and spectral study such as elemental analysis, molar conductance, UV–visible spectra, FT-IR spectra, H NMR and 13C NMR spectra. All complexes were stable in DMF solvent and the low molar conductivity confirms their stabilization and the non-electrolytic nature of them. The changes in the location and shape of the peaks in UV-visible, FT-IR, and the H and 13C NMR spectra of complexes rather than free ligand are the other evidence to form Schiff base complexes. The suggested structure of the complexes is pseudo-tetrahedral. Thermal behaviors of complexes were also investigated. Keywords:Schiff base, complex, diamine, spectra, thermal. Introduction Schiff bases are characterized by the HC=N- (imine) group which is important in illustrating the mechanism of the reactions in biological systems1-3 A wide range of Schiff bases have been synthesized due to the great flexibility and diverse structural aspects. Schiff base and its complex derivatives, especially heterocyclic amine family, have been an important field in drug research and development due to their broad bioactivities such as antitumor, antibacterial, and antiviral activities4,5. These complexes have also applications in clinical, analytical and industrial in addition to their important roles in reversibly bind oxygen in epoxidation reactions, biological properties7-9catalytic role in hydrogenation of olefins10,11, photochromic properties12, analytical determination13-15 and organic synthesis16. In these years, attention to group XII metal complexes with a stable d10 electronic configuration have been increased in the field of inorganic chemistry, biochemistry and environmental chemistry17,18. In continuation of our research19-21, the aim of this work is to prepare and investigate the some complexes of Cd(II) and Hg(II) with recently synthesized bidentate Schiff base ligand of N,N-bis [(E)-3-(2-nitrophenyl) allylidene)] benzene-1,2-diamine (L) with nitrogen atoms as donor sites21. The general formula of these complexes are MLX in which M= Cd(II) and Hg(II), L= Schiff base ligand and X= chloride, bromide, iodide. The ligand and complexes were characterized by physical and spectral data including microanalysis, FT-IR, UV-visible, H and 13C NMR and conductivity measurements. Material and MethodsGeneral: 2-Nitrocinnamaldehyde, 1,2-phenylendiamine, cadmium(II) and mercury(II) halides and other chemicals were purchased from either Aldrich, Merck or BDH Chemicals. All the chemicals used were of analytical grade. Solvents were purified and dried before use according to the standard method. FT-IR spectra in KBr pellets were recorded on a JASCO FT/IR-680 spectrometer in the 4000–400 cm-1 range. Electronic spectra were recorded in DMF solutions on a JASCO-V570 model spectrometer with quartz cells of 0.5cm path length. H and 13C NMR spectra were obtained using a Brucker DPX FT-NMR spectrometer at 500MHz with the samples dissolved in DMSO- mixture using TMS as internal standard. MS (m/z) of the ligand was recorded on Shimadzu model GC–MS QP5050. Carbon, hydrogen and nitrogen of dried samples were performed using an elemental analyzer. The melting points (C) of the complexes were recorded on BUCHI melting point B-545 instrument. Conductivity measurements of the ligand and their complexes were made on freshly prepared 10-3M solutions in DMF at room temperature with a Metrohm 712 conductometer with a dip-type conductivity cell made of platinum black. Preparation of N,N-bis [(E)-3-(2-nitrophenyl) allylidene)] benzene-1,2-diamine (L): The ligand was prepared as in our previous report21. The structure of the Schiff-base is presented in figure-1. Synthesis of complexes: The Schiff base ligand (1 mmol) in 20 mL methanol was added gradually to a same amount of metal salt (1 mmol) (MX, where M= Cd(II) and Hg(II); X= chloride, Research Journal of Recent Sciences ______________________________________________________________ ISSN 2277-2502Vol. 1(11), 9-15, November (2012) Res. J. Recent Sci. International Science Congress Association 10 bromide and iodide) in methanol or ethanol and then the mixture was vigorously stirred at room temperature for 4–6 h. When the solid product formed, the precipitate as complex was collected by filtration and then washed several times with warm methanol. The product was dried in air and stored in a desiccator over anhydrous CaCl under vacuum. All the metal complexes were stable to air and moisture.CdLCl FT-IR(KBr), cm-1: 3420(m), 3064(m), 2927(w), 2852(w), 1625(s), 1607(s), 1577(s), 1523(vs), 1440(m), 1343(vs), 1167(s), 986(m), 957(m), 787(m), 743(s), 677(m), 458(w). UV-visible(DMF), (nm) (,M-1cm-1): 284(47983) and 364(19422). 1HNMR spectra (in DMSO-d): 8.51(bs, 2H), 8.06(t, 4Hf,g', J= 9.16 Hz and J= 9.38 Hz), 7.79(m, 2Hf'), 7.69(d, 2H, J= 14.36 Hz), 7.66(t, 2H, J= 6.85 Hz and J= 7.80 Hz), 7.56(bs, 2H), 7.33(bs, 2H), 7.21(bs, 2H). 13CNMR spectra (in DMSO-d): 163.32(C), 149.08(C), 143.82(C), 139.04(C), 134.54(C11), 133.38(C10), 131.44(C12), 130.82(C), 129.37(C), 127.77(C), 125.57(C), 120.77(C). CdLBr FT-IR(KBr), cm-1: 3443(m), 3063(m), 2912(w), 2854(w), 1624(s), 1607(s), 1576(s), 1523(vs), 1441(m), 1343(vs), 1166(s), 984(m), 955(m), 786(m), 742(s), 678(m), 458(w). UV-visible(DMF), (nm) (,M-1cm-1): 284(48436) and 366(19586). 1HNMR spectra (in DMSO-d): 8.49(bs, 2H), 8.06(t, 4Hf,g', J= 7.31 Hz and J= 6.52 Hz), 7.80(t, 2Hf', J= 7.03 Hz and J= 7.24 Hz), 7.69(d, 2H, J= 13.84 Hz), 7.66(t, 2H, J= 6.87 Hz), 7.48(bs, 2H), 7.33(bs, 2H), 7.22(bs, 2H). CdLI FT-IR(KBr), cm-1: 3442(m), 3063(m), 2924(w), 2852(w), 1623(s), 1606(s), 1573(s), 1518(vs), 1443(m), 1344(vs), 1267(w), 1171(s), 990(m), 950(m), 786(m), 744(s), 680(m), 466(w). UV-visible(DMF), (nm) (,M-1cm-1): 284(45912) and 366(18863). 1HNMR spectra (in DMSO-d): 8.56(d, 2H, J= 7.06 Hz), 8.07(d, 2H, J= 8.24 Hz), 8.05(d, 2Hg', J= 8.15 Hz), 7.82(t, 2Hf', J= 7.51 Hz and J= 7.60 Hz), 7.69(d, 2H, J= 15.59 Hz), 7.67(t, 2H, J= 7.78 Hz and J= 7.73 Hz), 7.57(bs, 2H), 7.36(bs, 2H), 7.29(bs, 2H). 13CNMR spectra (in DMSO-d): 163.08(C), 149.09(C), 143.82(C), 139.09(C), 134.56(C11), 133.17(C10), 131.52(C12), 130.72(C), 129.29(C), 127.77(C), 125.62(C), 120.90(C). HgLCl FT-IR(KBr), cm-1: 3442(m), 3066(m), 2922(w), 2851(w), 1620(s), 1606(s), 1574(s), 1518(vs), 1439(m), 1343(vs), 1264(w), 1167(s), 984(s), 951(m), 789(m), 743(s), 678(m), 464(w). UV-visible(DMF), (nm) (,M-1cm):262(29106) and 318(19744). HNMR spectra (in DMSO-d): 8.68(bs, 2H), 8.07(d, 2H, J= 8.50 Hz), 8.01(d, 2Hg', J= 10.50 Hz), 7.80(m, 4Hf',c), 7.68(m, 6Hg,b,d), 7.34(m, 2H). 13CNMR spectra (in DMSO-d): 164.01(C), 149.07(C), 142.62(C), 139.10(C), 134.80(C11), 133.02(C10), 131.64(C12), 130.68(C), 129.11(C), 128.92(C), 125.62(C), 121.01(C). HgLBr FT-IR(KBr), cm-1: 3466(m), 3065(m), 2919(w), 2854(w), 1620(vs), 1607(s), 1573(vs) 1520(vs), 1440(m), 1343(vs), 1262(w), 1166(s), 984(s), 951(m), 788(m), 742(s), 678(m), 461(w). UV-visible(DMF), (nm) (,M-1cm-1): 264(36556) and 316(17292). HNMR spectra (in DMSO-d): 8.71(d, 2H, J= 8.50 Hz), 8.07(m, 4Hf,g'), 7.83(m, 2Hf'), 7.70(m, 6Hc,g,b), 7.43(m, 2H), 7.39(m, 2H). HgLI FT-IR(KBr), cm-1: 3466(m), 3062(m), 2919(w), 2854(w), 1623(s), 1605(s), 1574(s), 1517(vs), 1443(m), 1344(vs), 1169(s), 986(m), 951(m), 786(m), 759(m), 745(s), 679(m), 457(w). UV-visible(DMF), (nm) (,M-1cm-1): 262(45476) and 310(28862). HNMR spectra (in DMSO-d): 8.08(m, 4Ha,f), 7.83(m, 2Hg'), 7.73(m, 6Hf',c,g), 7.41(m, 2H), 7.38(m, 4He,d). N N 1 101211 N+OO- , e ,d,b,c,f,f',g,g',a X Figure-1 Suggested structure for the ligand and complexes (M=Cd(II), Hg(II) and X=Cl, Br, I) Results and DiscussionSynthesis: N,N-bis-[(E)-3-(2-nitrophenyl)allylidene)]benzene-1,2-diamine(L) as a Schiff base ligand was synthesized by the condensation reaction between 2-nitrocinnamaldehyde and 1,2-phenylendiamin as reported in previous report20,21. This ligand was used as chelate ligand to prepare complexes of Cd(II) and Hg(II) with general formula MLX in which X= Cl, Br, I. All complexes are insoluble in common solvent such as dichloromethane, chloroform, acetone and alcohols but they are soluble in dimethylsulfoxide and dimethylformamide. According to the information recorded by elemental analyses, the stoichiometry of ligand and its complexes was confirmed. The analytical and physical data of the Schiff base ligand and its complexes are given in table-1. The analytical data show that the 1:1 ratio (metal: ligand) is correct for all complexes. The molar conductivity was measured in DMF (10-3 M) at room temperature and low range of the obtained values 19.43-32.44 cm-1mol-1 indicates that the nature of all complexes is non-electrolyte22-24. IR spectra:The most characteristic absorptions of the bidentate Schiff base ligand and its complexes are summarized in table-2. In the IR spectrum of ligand, the absorption peak assigned to azomethine (-CH=N-) as a functional group, is appeared at 1609 cm-1. This stretching frequency shifted to higher frequency in all mercury and cadmium complexes. The shifting to the higher Research Journal of Recent Sciences ______________________________________________________________ ISSN 2277-2502Vol. 1(11), 9-15, November (2012) Res. J. Recent Sci. International Science Congress Association 11 frequency 1620-1625 cm-1 indicated this group was affected by complexation 24, 25. In the IR spectrum of ligand, the absorption band of CHaromatic and CHaliphatic appeare at 3057 and 2916 cm-1respectively that after complexation shifted to higher frequency. The peak at 2856 cm-1 assigned to iminic CH shifted smoothly to lower frequency after complexation. Two very sharp peaks assigned to asymmetric (asym) and symmetric (sym) streching band of nitro-group exist at 1519 and 1347 cm-1 that smoothly change in the IR spectra of complexes. The very strong out-of-plane bending of the aromatic C-H and C-C at 734 and 698 cm-1are shifted to higher or lower frequencies after coordination. The important absorption band in the spectra of complexes attributed to stretching frequency of M-N bound are appeared in the region of 457-466 cm-1 26. This peak confirmed that the nitrogen of ligand is successfully coordinated to the metal ion. Electronic Spectral Studies: Electronic spectra of the ligand and its complexes were recorded in DMF solvent at room temperature and the spectral data including the maximum wavelength are summarized in table-2. In the spectrum of ligand two absorption bands were appeared. An absorption band at 278 nm assigned to  transition of the aromatic ring moieties that shifted to the higher wavelength in the spectra of cadmium complexes while in mercury complexes this band has a shift to the lower wavelength. The other band at 374 nm attributed to  transition of imine groups which is mainly localized within the iminic chromophore. In the electronic spectra of all complexes, shifting to the lower wavelength (310-366 nm) suggest the coordination of the iminic nitrogen to the metal ions. The electronic spectra of d10 elements generally consists ligand to metal charge transfer (MLCT) that in our complexes were not separately observed (probably overlapped with internal transition of the ligand)27. The suggested structure of d10-four coordinated complexes based our evidences and with considering our previous report on this type of ligands 28-30 is pseudo-tetrahedral as drawn in figure-1. The FT-IR spectra of CdLCl and HgLCl are illustrated in figure-2. H and 13C NMR spectra: The H and 13C NMR spectra of complexes were recorded in DMSO-d at 300 MHz and were assigned based on figure-1. Detailed assignment of NMR spectra has been brought in experimental section. The H NMR spectrum of the ligand as in our previously report 21 showed the signal of iminic proton resonance as a functional group for Schiff base compound at 8.33 ppm as a doublet due to coupling with H. This signal has a red shift at all of complexes spectra and also in the H NMR of CdLCl, CdLBr and HgLCl is appeared as broad singlet. At HgLI spectra, this peak was overlapped with the signal of H and was exhibited as a multiplet signal. The change in the location and shape of iminic proton resonance signals confirm the coordination of imine nitrogen to metal. In the spectrum of ligand, the resonances of and Hg' were shown at 8.03 and 8.01 ppm as a doublet signals that after complexation smoothly shifted to the weaker fields except for HgLI that in which, the signal of Hg' shifted to 7.83 ppm as a multiplet signal. In the spectrum of ligand, H is observed at 7.24 ppm as a doublet of doublet due to coupling with H and H respectively. The signal of H is seen at 7.61 ppm as a doublet due to coupling with H. The signal of H and in the spectra of complexes have a smoothly shift to the down fields with respect to free ligand. The doublet of doublet signals at 7.23 and 7.10 ppm attributed to H and H of ligand are shifted to weaker fields in spectra of complexes as broad singlet and multiplet signals in Cd(II) and Hg(II) complexes respectively. In the spectrum of the ligand, Hf' is observed at 7.75 ppm as triplet due to coupling with the H and Hg'. H is appeared similar to Hf' at 7.59 ppm as triplet due to its couplings with H and Hf'. After coordination ligand to metals, these signals have smoothly shifted to the weaker fields. The 13C NMR spectrum of the ligand shows the iminic carbon (C) resonances as functional group signal at 144.36 ppm. This peak is shifted to 142.62-143.82 ppm in the complexes, suggesting well coordination of the iminic nitrogens to metal ions. The other peaks of aromatic and ethylenic carbons resonance are observed at 162.74(C), 148.109(C), 137.62(C), 133.57(C11), 132.80(C10), 130.10(C12), 129.94(C), 128.56(C), 126.58(C), 124.53(C), 120.21(C) that shifted to the down field after formation of Schiff base complexes. The good 13CNMR spectra were not recorded for some complexes as seen their absence in experimental section.Table-1 Synthetic, analytical and conductivity data for the mercury and cadmium complexes. Compound Color M.p.( o C) Yield(%) Found (Calcd.) (%) M (cm-1-1) C N H CdLCl Yellowish White 294(dec.) 71 47.18 (47.28) 9.22 (9.19) 2.82 (2.98) 19.43 CdLBr 2 Yellowish White 247(dec.) 77 - - - 20.06 CdLI 2 Yellowish White 258(dec.) 73 - - - 30.51 HgLCl Yellowish White 184(dec.) 71 40.84 (41.30) 8.32 (8.03) 2.55 (2.60) 28.10 HgLBr 2 Cream 178(dec.) 85 - - - 32.44 HgLI 2 Yellow 198(dec.) 78 - - - 31.68 Research Journal of Recent Sciences ______________________________________________________________ ISSN 2277-2502Vol. 1(11), 9-15, November (2012) Res. J. Recent Sci. International Science Congress Association 12 Table-2 FT-IR (cm-1) and UV–visible (nm) spectral data of the Schiff-base ligand21 and its mercury and cadmium complexes Compounds CH (arom.) CH (aliph.) CH (imin.) C=N C=C (–NO) CH arom(oop) C-C arom(oop) M–N max Ligand 3057 2916 2856 1609 1583 1519, 1347 734 698 - 278, 374 CdLCl 3064 2927 2852 1625 1607 1523, 1343 743 677 458 284, 364 CdLBr 3063 2912 2854 1624 1607 1523, 1343 742 678 458 284, 366 CdLI 3063 2924 2852 1623 1606 1518, 1344 744 680 466 284, 366 HgLCl 3066 2922 2851 1620 1606 1518, 1343 743 678 464 262, 318 HgLBr 3065 2919 2854 1620 1607 1520, 1343 742 678 461 264, 316 HgLI 3062 2919 2854 1623 1605 1517, 1344 745 679 457 262, 310 a B c d Figure-2 FT-IR of CdLCl(a), HgLCl(b) and UV-visible of CdLCl(c), HgLCl(d) in compared to ligand Research Journal of Recent Sciences ______ _ Vol. 1(11), 9-15, November (2012) International Science Congress Association a c 1 H NMR of CdLCl Thermal behavior of the complexes: Thermal decomposition of the titled complexes was runned from room temperature to 700C at the heating rates of 10 ( C/minute) under oxygen atmosphere. For instance, TGA plot of HgLCl figure-4. The lack of weight loss under 200 C water molecules in their structures. Complexes lose 78.4 _ ________________________________ ______________ International Science Congress Association b d Figure-3 H NMR of CdLCl (a), HgLCl(b) and 13 C NMR of CdLCl(c), HgLCl (d) Figure-4TGA plot of HgLCl complex Thermal decomposition of the titled complexes was runned from room temperature to C/minute) under oxygen atmosphere. For instance, TGA plot of HgLCl is shown in C states absence of water molecules in their structures. Complexes lose 78.4 -96.7% of their weight via two temperature steps at the applied temperature range. It is suggested that mercury(II) and cadmium(II) oxide are main metal residue. The weight loss% of complexes at various temperature steps are summarized in table 3. ______________ _________ ISSN 2277-2502 Res. J. Recent Sci. 13 (d) of their weight via two temperature steps at the applied temperature range. It is suggested that mercury(II) and cadmium(II) oxide are main metal residue. The weight loss% of complexes at various temperature steps are summarized in table - Research Journal of Recent Sciences ______________________________________________________________ ISSN 2277-2502Vol. 1(11), 9-15, November (2012) Res. J. Recent Sci. International Science Congress Association 14 ConclusionIn this paper we reported synthesis and identified a bidentate ligand and its mercury and cadmium complexes. The compounds were characterized by physical, spectral data and conductivity measurement. It was found that the complexes are non-electrolyte in DMF solution. Thermal investigation of the complexes showed that they are decomposed via two temperature steps in the range of room to 700°C. 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