ꢁꢀꢀꢀ
N. Beynek et al.: New Schiff base lead (II) complexꢂ
ꢂ149
Bashall, A.; McPartlin, M.; Murphy, B. P.; Powell, H. R.; Waikar, S.
Interaction of environmentally important metal-ions with
nitrogen sulfur-donor macrocycles – the crystal-structures
of 7-co-ordinate lead(II) and mercury(II) complexes of an
18-membered N4S2 macrocycle. J. Chem. Soc. Dalton Trans.
1994, 1383–1390.
Beynek, N.; McPartlin, M.; Murphy, B. P.; Scowen, I. J. Ligand control
of molecular helicity in the coordination of toxic heavy metal
ions: crystal structure of a monohelical cadmium complex(II)
complex. Polyhedron 1998, 17, 2137–2140.
Beynek, N.; Uluçam, G.; Benkli, K.; Koparal, A. T. Synthesis and
characterization of new binaphthyl-linked phenanthroline-,
bipyridine-, or pyridine-derived ligands, and the study of their
cytotoxic activity. Helv. Chim. Acta 2008, 91, 2089–2096.
Cannon, R. D.; Chiswell, B.; Venanzi, L. M. Some complexes of
cobalt(2) nickel(2) and palladium(2) with multidendate ligands
and ligand field strength of co-ordinated ethers and sulphides.
J. Chem. Soc. A- Inorg. Phys. Theo. 1967, 1277–1281.
Davidovich, R. L.; Stavila, V.; Marinin, D. V.; Voit, E. I.; Whitmire, K.
H. Stereochemistry of lead(II) complexes with oxygen donor
ligands. Coord. Chem. Rev. 2009, 253, 1316–1352.
Dietrich, B.; Viout, P.; Lehn, J.-M. Macrocyclic Chemistry, Aspects of
Organic and Inorganic Supramolecular Chemistry; Wiley-VCH:
Weinheim, 1995; Vol. 1 and 2.
Macrocyclic Schiff base complex [PbL](ClO4)2·2H2O:ꢁ2,2′-Bipyridine-
6,6′-dicarboxaldehyde (7) (0.221 g, 1.0 mmol) was dissolved in MeOH
(20 mL) containing Pb(ClO4)2·H2O (0.424 g, 1.0 mmol). The solution was
stirred vigorously and heated while a methanolic solution of 6-methyl-
6′-(2-aminophenoxymethyl)-2,2′-bipyridine (6) (0.60 g, 2.0 mmol) was
added slowly. The resultant solution was refluxed for 4–5 h and filtered
hot. The solvent of the reaction mixture was reduced to half its original
volume, and then the mixture was placed in a refrigerator to induce
precipitation. The yellow powder product was filtered and dried. Yield
0.65 g, 55%. νmax/cm-1; 3535 br (OH), 1618 m (Cꢀ=ꢀN), 1585 m, 1487 m,
1439 m, 1370 w, 1291 w, 1260 m, 1232 w, 1180 w, 1154 w, 1085 vs. (ClO4-),
1035 m, 999 m, 907 w, 784 s, 761 m, 669 w, 620 vs. (ClO4-), 592w. H
1
NMR (300 MHz; acetone-d6): δ 2.83 (6H, s, CH3), 5.80 (4H, s, CH2),
6.93 (2H, d, J 7.9 Hz), 7.16 (2H, t, J 7.1 Hz), 7.28–7.49 (10H, m), 7.68
(2H, t, J 7.8 Hz), 7.81 (2H, d, J 7.9 Hz), 7.87 (2H, d, J 7.5 Hz), 8.36 (2H,
d, J 7.6 Hz), 8.68 (2H, t, J 7.9 Hz), 8.93 (2H, d, J 8.3 Hz), 9.40 (2H, s,
-1
HCꢀ=ꢀN). ΛM (Ω mol-1 cm2) (acetone, 10-3 m) 26.0°C: 155 (2:1). μeff (BM),
24°C: 1.03. Electronic spectrum (DMSO). λmax: 348 nm π→π* (Cꢀ=ꢀN)
, 293 nm π→π* (aromatic ring). MALDI-TOF (m/z): found: 1064.68,
calc.: 1064.24 for [Pb-208(L-H)(ClO4)]; found: 964.890 calc: 965.281
+
+
for [Pb-208(L-H)] ; found: 782.815, calc: 782.302 for [L+Na] ; found:
756.880, calc: 757.304 for [L-H]- (Table 1). Anal. calc. for C48H42N8O12
Cl2Pb; C 48.00; H 3.52; N 9.33; found: C 48.22; H 3.72; N 9.24.
Fenton, D. E.; Murphy, B. P.; Leong, A. J.; Lindoy, L.F.; Bashall, A.;
Mc-Partlin, M. Studies of metal-ion recognition – the interaction
of Co-II, Ni-II, and Cu-II with new oxygen-nitrogen donor macro-
cycles – x-ray structures of complexes of Cu-II and Ni-II with a
15-membered O2N3 derivative. J. Chem. Soc. Dalton Trans. 1987,
2543–2553.
Geary, W. J. The use of conductivity measurements in organic
solvents for the characterisation of coordination compounds.
Coord. Chem. Rev. 1971, 7, 81–122.
Gerbeleu, N. V.; Arion, V. B.; Burgess, J. Template Synthesis of Mac-
rocyclic Compounds; Wiley-VCH: New York, 1999; Vol. 1 and 3.
Gill, N. S.; Nutall, R. H.; Scaife, D. E. The infra-red spectra of pyridine
complexes and pyridinium salts. J. Inorg. Nucl. Chem. 1961, 18,
79–87.
Gomez, D. E.; Perez, T. E.; Martinez, R. F.; Iglesias, M. M.; Iglesias, C.
P.; de Blas, A.; Blas, T. R. Lead(II) complexes of lateral macrobi-
cyclic receptors that incorporate a crown moiety and a pyridine
head unit. Eur. J. Inorg. Chem. 2010, 31, 5027–5034.
Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Homocoupling
of aryl halides using nickel(II) complex and zinc in the presence
of Et4NI. An efficient method for the synthesis of biaryls and
bipyridines. Bull. Chem. Soc. Jpn. 1990, 63, 80–87.
Izatt, R. M.; Christensen, J. J. (Eds.). Synthesis of Selective Agents;
Progress in Macrocyclic Chemistry; Wiley: New York, 1987;
Vol. 3.
Antibacterial and antifungal assays:ꢁThe microdilution broth method
was used in antimicrobial activity studies according to CLSI (Clinical
Laboratory Standards Institute) standards (National Committee for
Clinical Laboratory Standards, 1997, 2002). Bacterial strains used in
this study were E. coli ATCC 25922, L. monocytogenes ATCCF19115, and
S. thphimurium ATCC 14028 as Gram-negative; S. aureus ATCC 25923
and B. cereus ATCC 11778 as Gram-positive bacteria; and standard
yeast strain was C. albicans ATCC 10231. Different concentrations of
the complex [PbL](ClO4)2·2H2O (0.5; 1.0; 2.0; 4.0; 8.0; 16.0; 32.0; 64.0;
128.0 μg mL-1) in DMSO (1%) solution of culture medium were prepared
in 96-well flat-bottomed microculture plates by the double dilution
method. Afer micro-plates were prepared and inoculated, they were
incubated for bacteria at 37°C for 24 h. The inoculum density of each
bacterial and fungus isolate was standardized with 0.5 McFarland tur-
bidity standards. The suspension had a final inoculum of 5ꢀ×ꢀ107 cfu mL-1.
The MIC were defined as the lowest concentration of the compound
giving complete inhibition of visible growth. Antimicrobial effects of
[PbL](ClO4)2·2H2O were investigated against test microorganisms. The
solvent, DMSO (1%), used for the preparation of compounds did not
show inhibition against the tested organisms. The serial dilutions of an
antibacterial agent without microorganism was used as negative con-
trol, whereas media with ampicillin (standard antibiotic) and ampho-
tericin B (standard antifungal drug) were used as the positive controls
and media with microorganism was used as growth control.
Lindoy, L. F. The Chemistry of Macrocyclic Ligand Complexes;
Cambridge University Press: Cambridge, 1989; pp 21–90,
185–191.
Martinez, P. E.; Martinez, B. N.; Rodriguez, N. P.; Reyes, L. H.;
Del Rio, I. Polyaza macroligands as potential agents for heavy
metal removal from wastewater. J. Serb. Chem. Soc. 2013, 78,
591–602.
Mewis, R. E.; Archibald, S. J. Biomedical applications of macrocyclic
ligand complexes. Coord. Chem. Rev. 2010, 254, 1686–1712.
Nakamoto, K. Infrared and Raman Spectra of Inorganic and
Coordination Compounds, 5th ed.; Wiley: New York, 1997;
pp 252–256.
Acknowledgments: The authors thank the Trakya Uni-
versity for financial support under the research grant no.
TUBAP-2013/29.
References
Adatia, T.; Beynek, N.; Murphy, B. P. Helical group 12 co-ordination.
The x-ray crystal structure of a five-co-ordinate zinc(II) complex.
Polyhedron 1995, 14, 335–338.
Brought to you by | Monash University Library
Authenticated
Download Date | 12/12/15 1:39 AM