IJIPBART (2015) Volume 2, Issue (3), pp: 196- 207 ISSN: 2349-865X
OPEN ACCESS
International Journal of Innovation in Pharma
Biosciences and Research Technology (IJIPBART)
Original Research Article
www.refsynjournals.com 196
Studies on Mefenamic Acid complexes of Mn(II), Ni(II) and
Zn(II)
L.Shahanaz1, U.Punitha
1*
1Department of Chemistry, Dhanalakshmi Srinivasan College of Arts and Science for Women, Perambalur -
621212, India.
ABSTRACT
INTRODUCTION
Coordination chemistry is the study of compounds formed when the central metal ion is
closely bound to a ligand forming a complex ion or complex ions can be bound to other ions which
neutralize the charge of the complex ion. The progress in the field of bioinorganic chemistry is solely
dependent on the presence of coordination compounds in the living system (Adams and Cobe, 1969,
Smith, 1966, Sarelt, et al., 1963, Silverstein et al., 2014 and Karn et al., 1969). A vast number of
organic ligands and their complexes have been established as an integral part of the field of
coordination chemistry (Curtis, 1960). The third transition elements have been the centre of attraction.
The spectral and magnetic properties of the coordination compounds of these metal ions enable one to
predict the stereochemistry of these compounds with a fair amount of accuracy. Literature study
clearly reveals that transition metal ions have been studied extensively (Cabbiness and Margerum,
1970).
The ability of transition metals to exist in various oxidation states makes them important
industrial and biological catalysts (Jayabalakrishnan and Natarajan, 2001). The coordination
behaviour of metal ions, anionic and organic carboxylate ligands has been investigated by several
Article received
July 08, 2015
Article accepted
July 18, 2015
Article published
September 30, 2015
*Corresponding Author:
U. Punitha,
Dept. of Chemistry,
Dhanalakshmi Srinivan College
of Arts and Science for Women,
Perambalur-621212, India.
The study deals with the preparation and characterization of transition
metal complexes. The transition metal complexes were prepared with
mefenamic acid as ligand. Four complexes were prepared using
Mn(II), Ni(II) and Zn(II) ions. Their structures were assigned on the
basis of analysis, conductance, magnetic moment, UV-visible and FT-
IR spectral data. All the complexes were found to be ionic. Mn(II),
Ni(II) and Zn(II) complexes were found to be octahedral. The
biological activity of these ligands and its metal complexes against
anti-inflammatory agents could be studied.
Keywords: Mefenamic acid, 2- [bis(2,3-dimethylphenylamino
benzoic acid), magnetic moment, biological activity, UV Spectra, FT-
IR
Punitha et al IJIPBART (2015) Volume 2, Issue (3), pp: 233-244
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works. Only a few attempts have been made on the usage of carboxylic acids as neutral ligands with
metal halides, sulphates and nitrates (Chohan, 1997). Coordination compounds have been used in the
treatment, management and diagnosis of diseases. Many enzymes depend on metal ions. Literature
survey also reveals that some of the biologically active molecules which are used as chemotheraptic
agents have not been investigated for their complexing behaviour with transition metal ions. In this
study, an attempt is made to study the coordination behavior of biologically active mefenamic acid.
The coordination behaviour of divalent and trivalent metal chlorides, sulphate and nitrate with
mefenamic acid ligands has been extensively studied. The term anti-inflammatory agent has been
assigned to a drug that inhibits any fact of inflammation of an experimentally induced nature (or) as
part of a clinical syndrome. The biological activity of these ligands and its metal complexes against
anti-inflammatory agents could be studied.
Mefenamic acid (N-(2,3 xylyl) anthranilic acid (or) 2 - [bis(2,3 - dimethyl phenyl amino)
benzoic acid) is a white light yellow micro crystalline powder with molecular formula C14H15No2 and
molecular weight 241.29. The compound melts at 230oC and is insoluble in water, but soluble in
alkali hydroxides and alcohol. It is non-flammable and non-hygroscopic. It is not explosive and
fluoresces in 0.1% solution in chloroform with pale colour under UV light. It is used as an
antiphogesic, analgesic, antipyretic, antispasmodic and an anti-inflammatory agent. It is used in the
treatment of rheumatic (or) musculoskeletal disorders, rheumatoid arthritis, dysmenorrhea and acute
gout (Sabastiyan and Venkappayya., 1990).
In 1951, Reid and later Chenoweth (1979) suggested that the biological activity of aspirin was
due to its ability to form metal complexes. Suso and Edwards (1972) reported the presence of zinc-
aspirin complex in intestinal content, blood plasma and intestinal mucosa and suggested that aspirin-
zinc complex in the intestine binds the protein in the mucosa. Salunke et al., (2011) synthesized,
characterized, and studied the biocidal activities of Fe(III), Co(II), Zn(II), Cd(II), Y(III), and In(III)
complexes of Schiff base derived from L-Phenylalanine. Sreedaran et al., (2008) suggested that Ni(II)
and Cu(II) complexes derived from Salicylaldehyde 1-5 methyl salicylaldehyde and ethylene diamino
or diaminomalsonitrile (DMN) were synthesized. Jamuna et al., (2011) studied the synthesis,
characterization and biological activity of Cu(II) and Ni(II) complexes derived from tridentate shiff
base ligand 3-hydroxy-4(pyridine-2methyleneamino) benzoic acid. Patel et al., (1989) studied mixed
ligand complexes of Vanadium (V) which is used as the extraction system for vanadium. Fiabane et
al., (1978) studied the visible spectra and molecular filtration studies on Cu (II) acetate. El-Sirafy,
I.H., and El-Boray, N.A. (1985) found that novel eight metal complexes can been synthesized by
mixing Co(II), Ni(II), Cu(II) and Pd(II) complex with [N4] ligand. Sorenson (1976) reported that
Cu(II) acetate is effective in decreasing tumor growth with increasing survival suppressing metastasis.
The literature study did not reveal the publication of any investigation on the complexation of
mefenamic acid with transition metal ions. Hence it is proposed to prepare metal complexes of
mefenamic acid and investigate their structure from physicochemical studies. The most prominent
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metal ions which are biologically important in the 3d-series namely Mn(II), Ni(II),Zn(II), and were
chosen for the preparation of complexes with mefenamic acid. The above biologically active metals
have been chosen for the present work to study the co-ordination tendency of ligand (L) mefenamic
acid which is also biologically active.
METHODS
General experimental Techniques and analytical methods
Metal salts such as Manganese sulphate, Nickel sulphate, Zinc chloride, Zinc sulphate and
salts were used as such as metals. Mefenamic acid tablets, obtained from western chemicals were used
as ligand. The powdered tablets were extracted with methanol and filtered. The filtrate on evaporation
yielded the ligand mefenamic acid. It melts at 230oC.
Preparation of Complexes
Manganese (II) sulphate complex was prepared by mixing Mefenamic acid and Manganese
(II) sulphate in a molar ratio of 6:1 in alkaline medium and refluxed for 6 hours. The solution was
then concentrated to half the volume and acidified with dilute hydrochloric acid. When it was cooled,
brown colour of the complex was separated. It was washed with water and dried over anhydrous
calcium chloride. Similarly, Nickel (II) sulphate complex, Zinc (II) chloride complex and Zinc (II)
sulphate complex were prepared by mixing Mefenamic acid with Nickel (II) sulphate, Zinc (II)
chloride and Zinc (II) sulphate in the molar ratio of 6:1 in alkaline medium respectively.
Analytical methods
Estimation of metals in complexes
Estimation of Manganese
Manganese ion concentration was estimated by the method of Willard and Greathouse (1917).
Estimation of Nickel
Concentration of Nickel was estimated by the method of Macdonald and Sirichanya (1969).
Estimation of zinc
Concentration of Zinc was estimated by the method of Macdonald and Sirichanya (1969).
Estimation of anions
Estimation of chloride
The chloride ion concentration was estimated by the method of Ramsay et al. (1955).
Estimation of Sulphate
The sulphate ion concentration was estimated by the method of Tatabai (1974).
Experimental Techniques
Magnetic properties
Magnetic susceptibility of the complex was determined at room temperature by the Gouy
method. The weight of the empty Gouy tube was measured in the absence and presence of the
magnetic field. In order to evaluate the value of the tube calibrant, the tube was filled with the
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calibrant Hg [Co(CNS)4] up to the mark and the weight was measured in the absence and presence of
magnetic field. The calibrant was removed and the Gouy tube was washed with water and acetone and
then dried. Then the tube was filled with different complexes and the weights were measured in the
absence and presence of fields. In all these cases, care was taken to avoid air locking due to imperfect
filling of the material in the tube. The packing was uniform throughout the column up to the mark.
Diamagnetic correction was applied in the calculation of molar magnetic susceptibility. From the
magnetic susceptibility the effective magnetic moment at room temperature was calculated.
Measurement of Molar conductance
Molar conductance in the solvent depends on the number of ions present in the solution,
degree of dissociation, mobility of ions and temperature. Thus from the molar conductance,
electrolytic nature of the complex may be found out. Conductance of the solution was measured using
conductivity bridge (Toshniwal, India). The solvent used was acetonitrile. All the measurements were
corrected for the conductance of the solvent by subtracting the conductance of pure solvent from that
of the solution.
Electronic spectra
The solvent used was methanol, the absorbance of the complex solution were determined
using Lambda-35 spectrophotometer (Hitachi, Japan) for various wavelengths ranging from 380nm to
900nm.
Fourier Transform-Infrared spectra
The Fourier transform-Infrared spectra of the free ligand and the complexes were recorded on
spectrum RXl, Fourier Transform–Infrared spectrophotometer in the range 4000 -4500cm-1
using KBr
pellet technique.
RESULTS AND DISCUSSION
General properties
All the complexes were colored. All of them were stable at room temperature and soluble in
methanol. Sacconi et al., (1964) performed investigation on the occurrence of tetrahedral forms of
substitued bis(N-alkylsalicylaldimino) nickel (II) complexes. Similarly, Pal et al., (2008) performed
synthesis of pyrazolones using microwave assisted technology. Ghammamy (2012) synthesised,
characterized and performed theoretical studies on nanocomplex.
Analysis of the complex
The percentage of the metal and the anion in the complexes were estimated volumetrically.
The results clearly showed that Mn (II), Ni (II) and Zn (II) complexes have 1:6 coordination.
Measurement of molar conductance
The molar conductance of the complexes was determined in acetonitrile. The molar
conductance of 10-3
M solution was reported in Table 1. The molar conductance expected for l: 0, 1:1,
1:2 and 1:3 electrolytes in acetonitrile are given below.
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Table 1. Molar conductance of the complexes
Molar conductance ohm-1
cm2mole
-1 Type of electrolyte
<50 1:0
50-150 1:1
150-200 1:2
200-300 1:3
Based on the analytical and conductance data the complexes were assigned the following
composition.
[Mn(MEF)6]SO4, [Ni(MEF)6]SO4, [Zn(MEF)6]Cl2 & [Zn(MEF)6]SO4
Magnetic Susceptibility Measurement
Generally it is found that the majority of manganese (II) complexes have high spin. The high
spin d5 configuration gives as essentially spin only magnetic moment of 5.98BM which is temperature
independent. The experimentally determined magnetic moments of manganese (II) sulphate
complexes is in the range of (5.91-5.95BM) at room temperature. Magnetic value was in accordance
with the high spin configuration showing the presence of octahedral ring for the sulphate complex. In
manganese five unpaired electrons were predicted. The mefenamic acid complexes of manganese (II)
have a magnetic moment of 5.92BM which is close to the spin only value. The majority of Nickel (II)
complexes have relatively simple behavior. In the octahedral field, two unpaired electrons are present.
The ground state makes no orbital contribution to the magnetic moment, so that these moments are
expected to be not greatly different from the spin only moment 2.82BM. They have different
temperature and are of small variation from octahedral geometry. A magnetic moment of 2.8-3.2BM
was associated with spin only octahedral Nickel (II) complexes. The mefenamic acid complex of
Nickel (II) has a magnetic moment of 2.83BM which is close to the spin only moment. Zinc (II)
complexes were found to be diamagnetic as expected for d10
Configuration. It has complete shell of
electron and there is no possibility to d-d transition. It has also octahedral geometry. Ito and Ito (1958)
studied the magnetic moments of copper (II) complexes.
Electronic Spectra and bonding
The d-orbitals were split differently on octahedral, tetrahedral and other arrays of ligands
according to crystal field theory formalism. The addition of electrons on these orbitals leads to the
observation of electronic spectra. These electronic transitions were the characteristic of geometry of
the complex. Hence, by comparison of the absorption maximum with the predicted value, the
geometry of the complex could be decided.
Manganese (II) complexes have d5 configuration and the ground state term for d
5
configuration is 6S5/2. The electronic spectra of Manganese (II) sulphate complexes consists of 5 spin
allowed transition in octahedral geometry. The manganese (II) sulphate complex displayed a band at
29,325 cm-1
. This band was assigned to 6A1g
4Eg(4D) transition of octahedral geometry. Nickel
(II) complexes have d8 configuration. The ground state term symbol for d
8 configuration is
3F4. The
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electronic spectra of Nickel (II) complex consists of only two spin allowed transition in an octahedral
geometry. The Nickel (II) sulphate complex displayed a band at 24,585 cm-1
. This band was assigned
to the 3A2g
2T1g(p) transition of octahedral geometry.
Zinc (II) complexes have d10
configuration. It has complete shell of electrons and therefore
there is no possibility of d-d transitions. The d10
configuration of zinc (II) ion along with the data
obtained confirms an octahedral structure around the ion. The zinc (II) complexes displayed a band at
46,948 cm-1
and are assigned to the peaks because of charge transfer.
Joshi et al., (1977) studied the IR spectroscopic data for the β-diketones and their
chelates. Shirin and Mukherjee (1992) synthesized and studied the spectra and electrochemistry of
ruthenium (III) complexes with Schiff-base ligands. Similarly, Singh and Sharma (2002) studied the
magnetic moments of Co2+
, Ni2+
and Cu2+
complexes with Schiff bases derived from Benzil
Monohydrazone. Wester and Palenik (1973) performed spectral studies on the novel pentagonal
bipyramidal complexes of iron(II), cobalt(II), and zinc(II).
Fourier Transform-Infra Red Spectrum
The assignment of systematic shifts in the position of FT-IR band gives some clues regarding
the mode of linkage in the complex. The wave number and band assignment for the ligand and the
complexes are given in Table 5. In the FT-IR spectra of complexes, the carbonyl frequency present in
the carboxylic acid group of mefenamic acid was very much shifted to lower frequency. The spectrum
of Mefenamic acid shows a band at 1651.62 cm-1
which was the C=O stretching of carboxylic group
on conjugation (ie) attached to the aryl group. It was shifted to 1610-1635cm-1
in the complexes. The
displacement of C=O frequency to lower wave number suggest the involvement of carbonyl oxygen
in coordination with the metal ion. The strong band at 1156.52 cm-1
which was the C-O stretching of
phenolic group was present. It was shifted to 1154-1026 cm-1
in the complexes. The displacement of
C-O frequency to lower wave number suggests the phenol in carbon oxygen in co-ordination with the
metal ion. The sharp band at 3309.67 cm-1
was due to O-H stretching in the ligand. It was found at
3747-3640 cm-1
in the complexes. The spectrum of mefenamic acid and the complexes showed a band
around 1934-1924cm-1
and this was due to C=C stretching frequency of mefenamic acid. The
spectrum of mefenamic acid and the complexes showed a band around 1328-1380cm-1
and this was
due to C-N stretching frequency of mefenamic acid. The band ranging from the 520-500cm-1
in the
spectra of complexes in spectrum of mefenamic acid could be due to M-O stretching frequency. The
spectrum of mefenamic acid and the complexes showed a band around 2918-2909cm-1
and this was
due to ortho substituted methyl group in the benzene ring of mefenamic acid. The spectrum of
mefenamic acid and the complexes showed the spectrum band on the normal N-H stretching
vibrations at 3308-3413cm-1
and this was due to the amino acids of mefenamic acid. Thus, the FT-IR
spectral studies revealed that the mefenamic acid was a non-ionic monodentate ligand. Temel (2004)
performed spectroscopic studies of metal ion complexes.
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Structure of the Complexes
The FT-IR spectrum and analytical data suggested that mefenamic acid was a non
monodentate ligand. The analytical, magnetic moment and electronic spectral data suggested an
octahedral geometry for Mn(II), Ni(II) and Zn(II) complexes. Raman
performed redox and antimicrobial activity studies of metal complexes. Similarly, Kumar
(2008) performed antimicrobial activity studies on quinazolinone derivatives.
(2010) performed in vitro antifungal
performed antimicrobial activity against metal ion complexes.
Figure 1. Geometry of Manganese (II) sulphate complexes, Nickel (II) sulphate complexes, Zinc
(II) chloride and Zinc (II) sulphate complexes of Mefenamic acid
Table 2. Colour and analytical data of the complex
MEF= Mefenamic acid
Sl.
No.
Complex
1. [Mn(MEF)6]SO4 Light brown
2. [Ni(MEF)6]SO4 Green
3. [Zn(MEF)6]Cl2 Yellowish white
4. [Zn(MEF)6]SO4 white
IJIPBART (2015) Volume 2, Issue (3), pp: 2
IR spectrum and analytical data suggested that mefenamic acid was a non
monodentate ligand. The analytical, magnetic moment and electronic spectral data suggested an
octahedral geometry for Mn(II), Ni(II) and Zn(II) complexes. Raman et al.,
performed redox and antimicrobial activity studies of metal complexes. Similarly, Kumar
(2008) performed antimicrobial activity studies on quinazolinone derivatives.
antifungal screening of metal complexes. Shrivastava
performed antimicrobial activity against metal ion complexes.
Geometry of Manganese (II) sulphate complexes, Nickel (II) sulphate complexes, Zinc
(II) chloride and Zinc (II) sulphate complexes of Mefenamic acid
Colour and analytical data of the complex
Colour Percentage of metal
Calculated Observed
Light brown 12.26 11.99
Green 9.14 10.08
Yellowish white 11.32 11.37
white 11.32 11.37
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202
IR spectrum and analytical data suggested that mefenamic acid was a non-ionic
monodentate ligand. The analytical, magnetic moment and electronic spectral data suggested an
et al., (2002 and 2003)
performed redox and antimicrobial activity studies of metal complexes. Similarly, Kumar et al.,
(2008) performed antimicrobial activity studies on quinazolinone derivatives. Kumar and Chandra
Shrivastava et al., (2009)
Geometry of Manganese (II) sulphate complexes, Nickel (II) sulphate complexes, Zinc
(II) chloride and Zinc (II) sulphate complexes of Mefenamic acid
Percentage of anion
Calculated Observed
7.80 7.71
12.8 12.4
7.54 7.28
8.1 8.8
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Table 3. Molar conductance at 31
Sl.
No.
Complex
1. [Mn(MEF)6]SO4 Acetonitrile
2. [Ni(MEF)6]SO4 Acetonitrile
3. [Zn(MEF)6]Cl2 Acetonitrile
4. [Zn(MEF)6]SO4 Acetonitrile
MEF=Mefenamic acid
Table 4. Magnetic moment and geometry of the complexes
Sl.
No.
Complex
1. [Mn(MEF)6]SO4
2. [Ni(MEF)6]SO4
3. [Zn(MEF)6]Cl2
4. [Zn(MEF)6]SO4
MEF=Mefenamic acid
Table 5. Electronic spectral data and band assignments
Sl. No. Complex
1. [Mn(MEF)6]SO4
2. [Ni(MEF)6]SO4
3. [Zn(MEF)6]Cl2
4. [Zn(MEF)6]SO4
MEF=Mefenamic acid
Table 6. Infra red spectral bands of mefenamic acid and Mn(II),Ni(II) and Zn(II) complexes
MEF=Mefenamic acid
Sl.
No.
Name
C=O
1. Mefenamic acid 1651.62 1156.52
2. [Mn(MEF)6]SO4 1611.72 1047.34
3. [Ni(MEF)6]SO4 1617.05 1034.19
4. [Zn(MEF)6]Cl2 1575.15 1046.84
5. [Zn(MEF)6]SO4 1634.04 1025.96
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Molar conductance at 31°c
Solvent Molar Conductance ohm-1
cm2 mole
-1
Nature of the
Acetonitrile 18.12
Acetonitrile 17.39
Acetonitrile 13.65
Acetonitrile 7.95
Magnetic moment and geometry of the complexes
µEff in B.M Number of predicted
unpaired electrons
5.92 5
2.83 2
_ 0
_ 0
Electronic spectral data and band assignments
Λ max in nm
(in CH3OH)
Assignment of
Transition
341 6A1g
338 3A2g
344 Charge Transfer
213 Charge Transfer
Infra red spectral bands of mefenamic acid and Mn(II),Ni(II) and Zn(II) complexes
Frequency in cm-1
C-O O-H C=C C-N M
1156.52 - 1934.64 1328.35 520.82
1047.34 3747.42 1928.81 1277.65 500.11
1034.19 3639.81 - - 505.74
1046.84 3745.60 1923.67 1279.63 505.90
1025.96 3745.42 - 1377.92 507.89
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203
Nature of the
Electroyte
1:0
1:0
1:0
1:0
Geometry
Octahedral
Octahedral
Octahedral
Octahedral
Assignment of
Transition
1g 4Eg(4D)
2g
2T1g(p)
Charge Transfer
Charge Transfer
Infra red spectral bands of mefenamic acid and Mn(II),Ni(II) and Zn(II) complexes
M-O CH str
in CH3
N-H
520.82 2910.38 3309.67
500.11 2917.25 3317.47
505.74 2917.67 3413.15
505.90 2915.39 3342.47
507.89 2909.43 3378.58
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Figure 2. UV Spectra of MnSO
Figure 3. FT-IR spectra of Mefenamic acid, MnSO
CONCLUSION
The present study deals
complexes with mefenamic acid as ligand. Four complexes were prepared with Mn(II), Ni(II) and
Zn(II) ions. Their structures were assigned on the basis of analysis, conductance, magnetic moments,
electronic and FT-IR spectral data. The nature of the ligand was established to be non
monodentate. All the complexes were found to be ionic. Mn(II),Ni(II) and Zn(II) complexes were
found to be Octahedral.
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IJIPBART (2015) Volume 2, Issue (3), pp: 2
UV Spectra of MnSO4.MEF, NiSO4.MEF, ZnCl2.MEF and ZnSO4.MEF
IR spectra of Mefenamic acid, MnSO4.MEF, NiSO4.MEF, ZnCl
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Zn(II) ions. Their structures were assigned on the basis of analysis, conductance, magnetic moments,
IR spectral data. The nature of the ligand was established to be non
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Cite this article in press as Punitha et al. (2015) Studies on Mefenamic Acid complexes of
Mn(II), Ni(II) and Zn(II), IJIPBART, 2(03); 233-244.
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