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SJPM-122Chelation Trends and Antibacterial Activity of Some Mixed Ligand Chelates9- ب35
SJPM-122Chelation Trends and Antibacterial Activity of Some Mixed Ligand Chelates9- ب35
Abstract: Synthesis and investigation of new Co(II), Ni(II), Cu(II), Zn(II) and Cr(III)chelates of mixed ligands including
aSchiff base [(E)-2-(4-(dimethylamino)benzylideneamino)phenol] (C15H16N2O) derived from the condensation of 4dimethylaminobenzaldehyde with 2-aminophenol as main ligand (L1) and an amino acid; L-Histidine as co-ligand (L2)
were studied. The obtained Schiff base and the mixed ligand chelates were subjected to several physiochemical
techniques, in terms of CHN elemental analyses, molar conductivity, magnetic moment measurements, infrared,
electronic and mass spectroscopies. The CHN analytical data showed the formation of the Schiff base compound and the
mixed ligand chelates in 1:1:1[M:L1:L2] ratio. All the prepared mixed ligand chelates were non-electrolyte in nature.
The infrared spectral data exhibited that the used ligands behaving as bidentate ligands towards the metal ions. The
1HNMR spectra of the ligands and their Zn(II) mixed ligand chelate exhibited the effect of the activated groups of the
ligands by the metal ion. The electronic spectral results showed the existence of * (phenyl ring) and n*(HC=N)
and suggested the geometrical structures of the chelates. Meanwhile, the mass spectral data revealed the fragmentations
of the Schiff base, Histidine and their Cu(II) mixed ligand chelate. The studies made on these chelates proposed a six
coordinated octahedral geometry for all these chelates. The antibacterial activities of the Schiff base, Histidine, metal
salts and mixed ligand chelates were screened. It is found that the mixed ligand chelates have the most biological activity
in comparison to the free ligands and salts.
Keywords: Schiff base; 4-dimethylaminobenzaldehyde; 2-aminophenol; Histidine; mixed ligand chelates;
Physiochemical techniques; Antibacterial activity.
INTRODUCTION
The complexes of Schiff base derived from
the reaction of substituted aldehydes with aliphatic and
aromatic amines represent a series of compounds
containing nitrogen, oxygen and sulphur ligand donor
atoms that has been widely reported [1]. Bioactive
donor site of N, O and S atoms in organic ligand
moieties were widely used in the development of
different area such as metal based drugs, medicinal,
industrial, analytical, agricultural, biological and
clinical. The poly functional donor sites containing
Schiff base moieties were extensively used in the field
of analytical, biocidal, agrochemical, enzyme models,
catalysis, food, chemical and dye industries [2]. The
preparation and characterization of mixed ligand
complexes
derived
from
2,6pyridinedicarboxaldehydebis (o-hydroxyphenylimine)
or 2, 6-pyridinedicarbox- aldehydebis (p-hydroxy
phenylimine) and 2-aminopyridne have been studied
[3]. The mixed ligand chelates of Mn(II), Fe(III),
Co(II) and Cu(II) ions derived from catechol and 2aminobenzothiazole have been prepared and
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H2N
O
N
4-dimethylaminobenzaldehyde
ethanol
HO
CH
2-aminophenol
HO
(E)-2-(4-(dimethylamino)benzylideneamino)phenol
In case of M= Zn2+, Ni2+, Co2+ and Cu2+, X, Y= H2O , when M= Cr3+, X= H2O , Y= OH
n = 2 in case of Ni and Cu chelates, 6 in case of Co, 8 in Zn chelate and 4 in Cr chelate.
Chemical equation-1: Reaction between the ligands and metal ions
Scheme (2 ): The Synthesis Route of mixed ligand chelates
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Table 1: CHN elemental analyses , magnetic moments and conductivity of the mixed ligand chelates
Ligand/Chelates
M.
Wt
colour
Yield
(%)
C%
Calc.
C%
Exp.
%H
Calc.
%H
Exp.
%N
Calc.
%N
Exp.
BM
240.
Yellow
92.98
75.00
75.76
6.60
4.84
11.67
12.77
560
487
528
602
517
Olive gray
Lamp black
Burnt umber
yellow
pale Yellow
77.78
53.33
86.60
68.73
72.09
45.00
51.74
47.72
41.86
48.74
44.65
50.77
46.57
41.02
48.00
4.10
4.72
4.35
3.82
4.44
3.45
3.45
3.02
3.65
4.20
12.50
14.37
13.25
11.63
13.53
11.16
13.39
14.39
13.07
11.54
3.22
4.66
2.43
0.00
4.53
4.20
1.53
7.88
0.20
2.81
Schiff base ( L )
C15H16N2O
[CoL1L2(H2O)2].6H2O
[NiL1L2(H2O)2].2H2O
[CuL1L2(H2O)2].2H2O
[ZnL1L2(H2O)2].8H2O
[CrL1L2(OH)(H2O)].4H2O
Table 2: Infrared and electronic spectral data of Schiff base, Histidine and their mixed ligand chelates
CO
Ligand / Chelate
OH
NH2 C=N-H
M-O
M-N
nm (cm-1)
O
Schiff Base (L1)
3337
1588
375(26666)
Histidine (L2)
3017
3400
435(22988)
[Co(L1L2)(H2O)2].6H2O
3424
1602
615
470
310(32258), 380 (26316)
290(34482), 355(28169),
[Ni(L1L2)(H2O)2].2H2O
3409
1601
614
470
425(23529)
[CuL1L2(H2O)2].2H2O
3410
1595
415
465
425(23529), 490(20408)
344(42553), 385(25974),
[Zn(L1L2)(H2O)2].8H2O
3410
1608
615
460
460(21739)
[Cr(L1L2)(OH)(H2O)].4H2O
3409
1607
615
470
480(20833)
Proton nuclear magnetic resonance spectra(1HNMR)
In the present investigation, 1HNMR spectra
of the ligands and their Zn(II) chelate Figure-1 exhibit
signals at 7.50 and 8.70 ppm attributed to -OH and
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Table 3: Mass spectral fragmentation of Schiff base, Histidine and their Cu(II) mixed ligand chelate
m/e+
Compound
Fragmented ions
values
C15H16N2O
240
C15H14N2O+
238
C15H16N2O (L1)
C13H9NO+
195
C12H7O+
167
C5H4+
64
C6H9N3O2
155
C6H8NO+
110
C6H9N3O2 (L2)
C5H8N+
82
C3H4N+
54
CH2N+
28
[Cu(C15H16NO)(C6H9NO2)(H2O)]2H2O
528
[Cu(C19H16N4O2)]+
395
[Cu(C9H6N2O2)]+
237
[CuL1L2(H2O)2].2H2O
[Cu(C6H4NO2)]+
185
[Cu(C4H3NO)]+
144
C3H3O
55
Fig-2: Mass spectra of Schiff base, Histidine and Cu( II) mixed ligand chelate
32
Fig-3: Electronic spectra of Schiff base , Histidine and their mixed ligand
Antibacterial activity
The Schiff base (L1), Histidine (L2) and the
mixed ligand chelates were screened for their
antibacterial activity Table-3, figure 4. No effect was
observed for both Schiff base and Histidine on the five
types of tested bacteria. Whereas, the effect of all mixed
ligand chelates was observed. Most mixed ligand
chelates were resisted by Enterococcus faecalis and
Escherichia coli except [NiL1L2(H2O)2]2H2O mixed
ligand chelate had moderately effective, although the
effectiveness of copper chelate of the formula
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No.
1
2
3
4
5
6
7
8
9
10
11
12
S. aureus
0
0
25
28
15
20
21
14
22
12
15
9
2.
3.
4.
5.
REFERENCES
1. Neelakantan, M. A., Marriappan, S. S.,
Dharmaraja, J., Jeyakumar, T., & Muthukumaran,
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7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
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