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Institute of Science & Technology for Advanced Studies & Research (ISTAR), Mota Bazar, Vallabh Vidyanagar, Anand, Gujarat, India
ISSN: 0976-3031
Research Article
SYNTHESIS AND CHARACTERIZATION OF SCHIFF BASE ANILINE WITH 5-BROMO -2-
HYDROXYL BENZALDEHYDE AND THEIR METAL COMPLEXES
Mohammad Muzammil Y. Kuddushi., Mohammed Abrar H. Malek., Vinod L. Patidar
Mihir S. Patel., Roma K. Patel and Rohit H. Dave*
Institute of Science & Technology for Advanced Studies & Research (ISTAR), Mota Bazar, Vallabh
Vidyanagar, Anand, Gujarat, India
DOI: http://dx.doi.org/10.24327/ijrsr.2018.0904.1977
ARTICLE INFO ABSTRACT
A series of transition metal complexes of Cu (II), Co (II), Mn (II), Fe (II), Ni (II) and V (II) were
prepared from bidentate schiff base. The Schiff base ligand synthesized from the condensation of 5-
Bromo 2-Hydroxy Benzaldehyde (NEELIMA, D, KULKARNI; P, K, BHATTACHARYA. Can. J.
Chem. 1987, 65, 348) and Aniline in an alcohol medium. These metal complexes were characterized
on the basis of their analytical data like IR, NMR. The ligand and their metal complexes were
screened antibacterial activity against various bacteria like Escherichia coli, B. subtilis. The result
indicated that the complexes exhibited good antibacterial activities.
INTRODUCTION
Schiff bases derived from an amino compound and carbonyl
compound that coordinate to metal ions via azomethine
nitrogen atom (1). Azomethine (C=N) has been reported to
possess remarkable antibacterial, biological activities (2-3) but
copper complex with ligand have wide applications in food
industry, dye industry, analytical chemistry, catalysis,
fungicidal, agrochemical, anti-inflammable activity, antiradical
activities and biological activities (4). The complexes of Schiff
bases with metal ions are very important in the development of
coordination chemistry field. These complexes are also known
to have anticorrosion properties and biological activities such
as antimicrobial (5-21). Importance of Schiff bases and their
metal complexes are important as biochemical (22),
electrochemical (23), biological antibacterial activities (24-28),
redox catalysts (29, 30). The role of chlorophyll, hemoglobin,
carbonic anhydrase, vitamin B12, xanthine oxides and
haemocyanin, illustrates the intimate linkage between inorganic
chemistry and biology (31-37). The coordinate chemistry field,
a lot of Schiff bases operates as ligands (38-40). Some of the
Schiff bases complexes combinations with a metal ion are used
as insecticides, fungicides, herbicides (41).
MATERIALS AND METHODS
Synthesis of Bromo 2-Hydroxy Benz Aldehyde
A solution of bromine 0.02 moles in glacial acetic acid is added
slowly to a stirred solution of 0.02 mole Salicylaldehyde in
glacial acetic acid. During the addition, the reaction mixture is
kept in a cold-water bath. After the addition is over the reaction
mixture will be yellow colored due to excess of bromine. (42)
The reaction mixture is allowed to stand for 15-20 minutes at
room temperature and poured into crushed ice. Water is added
to remove colour. Separated product is filtered, washed with
cold water and crystallized from diluted alcohol. yield is
approximately 25 gm. and M.P. 106-1070C. (Figure 1)
Figure 1 Synthesis of 5-Bromo 2-Hydroxybenzaldehyde
Synthesis of ligand
The ligand was prepared by a modification of the reported
methods. The Schiff base ligand has been synthesized by
O
OH
Br2 in Gl. CH3COOH
O
OH
Br
2-Hydroxy Benzaldehyde 5-Bromo-2-Hydroxybenzaldehyde
Available Online at http://www.recentscientific.com
International Journal of
Recent Scientific
Research
International Journal of Recent Scientific Research
Vol. 9, Issue, 4(G), pp. 26026-26030, April, 2018
Copyright © Mohammad Muzammil Y. Kuddushi et al, 2018, this is an open-access article distributed under the terms of
the Creative Commons Attribution License, which permits unrestricted use, distribution and reproduction in any medium,
provided the original work is properly cited.
DOI: 10.24327/IJRSR
CODEN: IJRSFP (USA)
Article History:
Received 5th January, 2018
Received in revised form 20th
February, 2018
Accepted 8th March, 2018
Published online 28th April, 2018
Key Words:
Complexes, Schiff base, Metal Salt,
Antimicrobial activities, Ligand
Mohammad Muzammil Y. Kuddushi et al., Synthesis And Characterization of Schiff Base Aniline With 5-Bromo -2- Hydroxyl Benzaldehyde And Their Metal Complexes
26027 | P a g e
refluxing a mixture of 0.01 mole of 5-Bromo 2-Hydroxy
Benzaldehyde and 0.01 mole of Aniline in 50 ml super dry
ethanol refluxed for about 3hr. Schiff base thus formed was
cooled to room temperature and collected by filtration,
followed by recrystallization in ethanol and dried.(Figure 2)
Figure 2 Synthesis of ligand
Synthesis of metal complexes
Cu, Ni, Mn, V, Fe, & Co was used as metals for the derivation
of metal complexes. In the process, 0.02 mole Schiff base was
dissolved in 25 ml ethanol. To this solution, 0.01 mole of the
metal salt solution was added. This mixture was allowed to stir
and refluxed for 3 hours. The product was cooled and washed
with cool water. Obtained precipitates were then dried for
further application. (Figure 3)
Figure 3 Synthesis of metal complexes
RESULTS AND DISCUSSION
Schiff bases of 5-Bromo 2-Hydroxy Benzaldehyde and Aniline
and its complexes have a variety of applications including
biological, clinical and analytical. The coordinating possibility
of 5-Bromo 2-Hydroxy Benzaldehyde has been improved by
condensing with a variety of carbonyl compounds. An attempt
has been made to synthesize Schiff bases from 5-Bromo- 2-
Hydroxy Benzaldehyde with Aniline. Physical characteristics,
TLC data, IR data, and NMR data, of metal complexes are
given in (Table 1 and 2).
The analytical data of complexes revel 2:1 molar ratio (ligand:
metal) and corresponds well with the general formula ML2
(where M=Cu(II),Ni(II),Co(II),Mn(II), V(II) and Fe(II).(Table
1)
FTIR spectrum analysis
The IR spectra of the complexes are compared with that of the
ligand to determine the changes that might have taken place
during the complexation. The bands at 3438, 1587, 1614, 1181,
and 1275 cm-1 assignable to v OH (intermolecular hydrogen
bonded), C=C(aromatic), v C=N (azomethine), v AR-Br and v
C-O (phenolic) stretching modes respectively(43-45).The
absence of a weak broadband in the 3200-3400 cm-1 region, in
the spectra of the metal complexes, suggests DE protonation of
the intermolecular hydrogen bonded OH group on
complexation and subsequent coordination of phenolic oxygen
to the metal ion. This is further supported by a downward shift
in υ C-O (phenolic) with respect to free ligand [46]. On
complexion, the v (C=N) (47) band is shifted to lower wave
number with respect to free ligand, denoting that the nitrogen
of azomethine group is coordinated to the metal ion. The v C-N
band is shifted to lower wave number with respect to free
ligand, The IR spectra of metal chelates showed new bands in
between the 500-800 and 400-500 cm-1 regions which can be
assigned to v M-O and M-N vibrations (48) respectively The
IR spectra of Cu (II), Co (II) Mn (II) Fe (II) Ni (II) and V (II)
show a strong band in the 3050-3600 cm-1 region, suggesting
the presence of coordinated water in these metal complexes.
(Table 2)
NMR spectrum analysis
1H NMR spectrum
The 1H NMR spectrum of the Schiff base ligand was recorded
in Acetone-d6. In the 1H NMR spectra of Schiff base ligand, a
peak appeared at 5.35 ppm was assigned to the proton of the
phenolic group and a singlet peak appeared at 8.87 ppm was
assigned to protons of azomethine group. (Figure 4)
OH
Br OH
Br
CH=N
CHO
-
H
2
O
+
NH2
5-bromo-2-hydroxy benzaldehyde Aniline Schiff base (L)
CH=N
OH
Br
CH=N
N=HC
O
O
M
Br
Br
metal salt
ethanol
M
2
Schiff Base
metal complex of Schiff base
Here, M= V,Mn,Fe,Co,Ni,Cu
metal
Table 1 Physical data of Schiff base and their metal
complexes
Compound Molecular
weight (g) M.P.(°C) Color
Yield
%
(w/w)
RF
Value
Schiff base(L)
275.9 gm. 163 Yellow 98.08 0.57
L-Cu metal 612.52 gm. 253 Blue 81.02 0.65
L-Co metal 576.99 gm. 179 light green
78.33 0.73
L-Fe metal 604.82 gm. 201 Brown 92.56 0.54
L-V metal 599.92 gm. 186 pale yellow
30.54 0.69
L-Ni metal 607.67 gm. 212 Yellow 62.12 0.71
L-Mn metal 603.91 gm. 191 pale yellow
71.00 0.78
Table 2 FTIR Spectral Data
IR FUNCTIONAL GROUP DATA
Compound v (C=N) v (N-H) v (M-O)
v (M-N) v(C-Br)
Schiff base(L) 1614 3438 - - 1122
L-Cu metal 1610 3448 526 456 1168
L-Co metal 1616 3249 558 452 1116
L-Fe metal 1616 3437 543 459 1179
L-V metal 1614 3438 527 439 1170
L-Ni metal 1600 3439 557 457 1167
L-Mn metal 1616 3427 526 438 1169
Figure 4. 1H NMR spectrum
International Journal of Recent Scientific Research Vol. 9, Issue, 4(G), pp. 26026-26030, April, 2018
26028 | P a g e
13CNMR spectra
The 13C NMR spectrum of the Schiff base ligand was recorded
in Acetone-d6. In the 13C-NMR spectra of the metal
complexes, the signal appeared at 159.32 ppm (C7) was
assigned to azomethine carbon atoms (C=N). A signal at
161.87 (C13) was assigned to phenolic carbon. Phenyl rings of
ligand showed following signals 147.84(C1); 121.38(C2-C6),
119.01(C4), 129.45(C3-C5), 121.16(C8), 133.95(C9),
109.87(C10), 135.04(C11), 121.16(C12) ppm.. (Figure 5)
Biological Applications
Antimicrobial Activity
The procedure used for screening is as reported. (49-51). The
synthesized compounds dissolved in DMSO were examined
using Well Diffusion method. In this method, all glass wares
used were sterilized in a hot air oven. The gram-positive
bacteria-B. megaterium and gram-negative-Escherichia coli
were used. The viable bacterial cells were evenly swabbed onto
the Nutrient agar plates, were soaked in the different test
samples (concentrations 4, 15 & 30 mg/ml), drained and using
sterilized forceps placed in the agar plates. The plates were
then incubated for 48 hours at 370C. After the incubation
period, the zones of inhibition were measured in mm. The
ligands and the metal complexes show very good antimicrobial
properties against Escherichia coli and B. megatherium.
(Figure 6), (Table 3)
Acknowledgment
The authors are grateful to Dr. Akshaya Gupte and Mr. Darshan
Rudaliya, N.V.P.A.S College, Anand for antimicrobial activities study
and SICART, Anand for FTIR and NMR studies.
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26029 | P a g e
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How to cite this article:
Mohammad Muzammil Y. Kuddushi et al.2018, Synthesis And Characterization of Schiff Base Aniline With 5-Bromo -2-
Hydroxyl Benzaldehyde And Their Metal Complexes. Int J Recent Sci Res. 9(4), pp. 26026-26030.
DOI: http://dx.doi.org/10.24327/ijrsr.2018.0904.1977
