Research Journal of Chemical Sciences ______________________________________________ ISSN 2231-606X
Vol. 5(5), 52-55, May (2015) Res. J. Chem. Sci.
Synthesis and Characterization of Schiff base m-nitro aniline and their
complexes
Muzammil K1, Trivedi P2 and Khetani DB1*
1
Dept of Industrial Chemistry, St. Xavier’s College, Ahmedabad, Gujarat, INDIA
2
Dept of Chemistry, St. Xavier’s College, Ahmedabad, Gujarat, INDIA
Available online at: [Link], [Link]
Received 21st April 2014, revised 27th April 2015, accepted 15th May 2015
Abstract
Schiff bases and their metal complexes has been a subject of research for longer period of time and till date it is. Various
researchers are aggressively focusing on synthesis of various schiff bases with different metal complexes and try to identify
their unique properties. Such an attempt made here to identify the antimicrobial properties of m-nitro aniline schiff base and
its two metal complex derivatives made up of copper and cobalt. Synthesis was confirmed by FTIR and antimicrobial activity
was determined using [Link] and [Link]
Keywords: Schiff base, m-nitro aniline, metal complex, antimicrobial activity.
Introduction Microwave methods have been popularly used in schiff base
synthesis by organic synthesis as it has several benefits like
Schiff base was invented by Hugo Schiff, which is named after better atom economy, environmental friendly, less hazardous,
him. Basically there are compounds with a functional group etc5-8.
those posses a carbon-nitrogen double bond with the nitrogen
atom connected to an aryl or alkyl group, not with hydrogen. In In general mechanism of synthesis of schiff base, an aromatic
general sense schiff bases, could be represented as the general amine reacts with a carbonyl compound by nucleophilic
formula R1R2C=NR3, where R is an organic side chain. Some of addition. This forms a hemiaminal, followed by a dehydration
them are restricted to the secondary aldimines (like azomethines to produce imines.
as the carbon is attached with a hydrogen atom) with the general
formula RCH=NR'1-3. Carbon-nitrogen double bond provides a Schiff bases obtained from aromatic aldehydes and aromatic
significant contribution in various progresses of chemical amines have a shown number of applications in many fields
sciences. Schiff-base compounds have been potentially used as including pharmaceutical, life sciences and chemical science
fine chemicals and medical substrates. Number of methods are including inorganic and analytical chemistry9-12.
been applied for synthesis of schiff base. In traditional method
of synthesis also known as organic synthesis, which commonly The aim of this study was to make schiff bases of m-nitro
involve the removal solvents from the reaction mixture or liquid aniline and their complexes, followed by characterization and
extraction especially in the case of aprotic dipolar solvent with antimicrobial activity determination of the schiff bases and
high boiling point, or product isolation through liquid-liquid metal complexes.
extraction1,4. Microwave-assisted reactions have been
intensively investigated as mentioned in previous study.
Figure-1
General reaction mechanism of schiff base
International Science Congress Association 52
Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X
Vol. 5(5), 52-55, May (2015) Res. J. Chem. Sci.
Figure-2
Reaction of Co complex with schiff base
Material and Methods indication of azomethene (CH=N). This reflects that amino acid
and aldehydes which are the substrate for synthesis have been
Synthesis of m-nitro aniline n-bezaldine Schiff base: converted into ligands. i.e. m-nitro aniline n- benzaldene.
Synthesis was started with 22.3 ml benzaldehyde, which was Similar kinds of observation were made by many other
mixed with 15 ml ethanol. After this 22.7 gm of m-nitro aniline researchers who have synthesized schiff bases using varieties of
(0.02M) was added to this alcoholic solution. The whole starting material4,13. In all the study a common effect was
mixture was stirred with addition of 2 to 3 drops NaOH observed where peaks of carbonate and amine were disappeared
solution. Mixture was allowed to reflux for 4 hours. After reflux upon addition of metal to the schiff base. Simultaneously new
cold water was added and solid yellow product was obtained. peaks were observed in the IR spectra depending on the schiff
Product was filter and dried for further use. base and metal.
Synthesis of metal complexes of Schiff Base: Cu and Co was Antimicrobial Activity: Results of antimicrobial activity reflect
used as metals for derivation of metal complexes. In the process that metal complex made up of Cu has more antimicrobial
2.6 gram schiff base was dissolved in 15 ml ethanol. To this activity than Co complex. This is because copper can directly
solution 0.02 mole of metal chloride solution were added. This affect bacteria in two steps: first it will rupture the cell
mixture was allowed to stir and refluxed for 3 hours. The membrane by direct interaction and second it creates holes in
the outer membrane, through which the cell loses vital nutrients
product was cooled washed with cool water. Obtained
and water, causing a general weakening of the cell and slow
precipitates were then dried for further application. death of cell14. Cobalt is not that much effective as copper.
FTIR Analysis: Fourier transforms infrared spectrophotometer Table-1
(FT-IR) analysis of each schiff base and its metal complexes Antimicrobial activity of metal complexes of schiff base
were done to confirm the formation of metal complexes. Schiff Base
and Metal Zone of inhibition (in mm)
Antimicrobial Activity: Antimicrobial activity was done by
Complex
agar cup method. One gram positive and one gram negative
microbe was selected for the study. For the assay, solutions with [Link] B. megaterium
desired concentration of schiff base with metal complexes were Ethanol - 12 ± 1
incubated with plates containing microbes and zone of CuCl2 18 ± 2 15 ± 2
inhibition was observed after 24 hrs. CoCl2 14 ± 1 15 ± 1
Ampliculin
Results and Discussion 19 ± 2 15 ± 1
Sodium
FTIR Analysis: Disappearances of carbonate and amine group
peaks from IR spectrum indicated formation of metal Conclusion
complexes. Here when spectra of schiff base and its metal
complexes were compared similar kind of observation was Based on overall study it was concluded that metal complexes
made. In the schiff base strong peaks of carbonate near 1723nm of schiff bases are more efficient antimicrobial agent than its
and amine near 3315nm were observed. Both of these peaks native form. However the antimicrobial potentiality is of metal
were absent in the IR spectra of metal complexes. In addition to complex is highly dependent in the metal ion used for formation
that another peak was observed near 1630nm which is an of metal complex.
International Science Congress Association 53
Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X
Vol. 5(5), 52-55, May (2015) Res. J. Chem. Sci.
Figure-3
FTIR spectra of schiff base
Figure-4
FTIR spectra of CoCl2 complex with schiff base
International Science Congress Association 54
Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X
Vol. 5(5), 52-55, May (2015) Res. J. Chem. Sci.
Figure-5
FTIR spectra of CuCl2 complex with schiff base
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