Studies on Mefenamic Acid complexes of Mn(II), Ni(II) and ... · PDF fileStudies on Mefenamic Acid complexes of Mn(II), Ni(II) ... study, an attempt is made ... assigned to a drug

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.

[email protected]

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


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



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



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.



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



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.

Punitha et al

www.refsynjournals.com

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


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


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

15) Volume 2, Issue (3), pp: 233-244

202

IR spectrum and analytical data suggested that mefenamic acid was a non-ionic


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


Percentage of anion

Calculated Observed

7.80 7.71

12.8 12.4

7.54 7.28

8.1 8.8

Punitha et al


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


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

15) Volume 2, Issue (3), pp: 233-244

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

Punitha et al


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.

REFERENCES

1. Adams, S.S., and Cobe, R. 1969.

West, Bulterworths, London, V, 59

2. Smith, M.J.H. 1966. In 'Salicylates' Ed. M.J.H. Smith and R.K. Smith, Wiley

Newyork, 49.

3. Sarelt, L.H., Patchelt, A.A., and Steelman, S.L. 1963.

4. Silverstein, R.M., Webster, F.X., Kiemle,

of organic compounds. 79-109.


UV Spectra of MnSO4.MEF, NiSO4.MEF, ZnCl2.MEF and ZnSO4.MEF

IR spectra of Mefenamic acid, MnSO4.MEF, NiSO4.MEF, ZnCl

ZnSO4.MEF

The present study deals with the preparation and characterization of transition metal



IR spectral data. The nature of the ligand was established to be non


Adams, S.S., and Cobe, R. 1969. In "Progress in Medicinal chemistry". Ed. G.P. Ellis and G.B.

West, Bulterworths, London, V, 59

Smith, M.J.H. 1966. In 'Salicylates' Ed. M.J.H. Smith and R.K. Smith, Wiley

Sarelt, L.H., Patchelt, A.A., and Steelman, S.L. 1963. "Prog. Drug. Res", 5: 13.

Silverstein, R.M., Webster, F.X., Kiemle, D., and Bryce, D.L. 2014. Spectrometric identification

109.

15) Volume 2, Issue (3), pp: 233-244

204

.MEF

.MEF, ZnCl2.MEF and

with the preparation and characterization of transition metal



IR spectral data. The nature of the ligand was established to be non-ionic


In "Progress in Medicinal chemistry". Ed. G.P. Ellis and G.B.

Smith, M.J.H. 1966. In 'Salicylates' Ed. M.J.H. Smith and R.K. Smith, Wiley- inter science,

"Prog. Drug. Res", 5: 13.

D., and Bryce, D.L. 2014. Spectrometric identification



5. Karn, J.L. and Busch, D.H. 1969. Nickel (II) complexes of the new macrocyclic ligands meso-and

(±)-2, 12-dimethyl-3, 7, 11, 17-tetraazabicyclo [11.3.1] heptadeca-1(17), 13, 15-triene. Inorg

Chem 8(5): 1149-1153.

6. Curtis, N.F. 1960. Transition metal complexes with aliphatic Schiff bases. Part I. Nickel (II)

complexes with N-isopropylidene-ethylenediamine schiff bases. J Chem 4409-4413.

7. Cabbiness, D.K., and Margerum, D.W. 1970. Macrocyclic effect on the stability of copper (II)

tetramine complexes. J Am chem Soc 91(23): 6540-6541.

8. Jayabalakrishnan, C., and Natarajan, K. 2001. Synthesis, characterization, and biological activities

of ruthenium (II) carbonyl complexes containing bifunctional tridentate schiff bases. Synt

React.Inorg Chem 31(6): 983.

9. Chohan, Z.H., Praveen, M., and Gaffar, A. 1997. Structural and biological behavior of Cu(II) and

Ni(II) metal complexes of some amino acid derived Schiff bases. 4(5).

10. Sabastiyan, A. and Venkappayya, D. 1990. Nickel (II) and Copper (II) complexes of

piperidinomethylurea. J Indian Chem Soc 67: 584.

11. Reid, R.A. 1951. The treatment of hypoprothrombinemia with orally administered vitamin K 1. Q

Bull Northwest Univ Med Sch 25(3): 292-295.

12. Chenoweth, D. 1979. Psychology of modeling in health education. Health education 10(4): 35-37.

13. Suso, F.A., and Edwards, H.M.J. 1972. Binding of EDTA, histidine and acetylsalicylic acid to

Zinc-protein complex in intestinal content, intestinal mucosa and blood plasma. Nature 236: 230-

232.

14. Salunke, M.H., Filmwala, Z.A., Dharap, S.B., and Kamble A.D. 2011. Synthesis, characterization,

spectral studies, biocidal activities of Fe (III), Co(II), Zn(II), Cd (II), Y(III), and In(III) complexes

of Schiff base derived from L-phenylalanine. Oriental J chem. 27: 1185-1191.

15. Sreedaran, S., Bharathi, K.S., Rahiman, A.K., Rajesh, K., Nirmala, G., Jagadish, L., Kaviyarasan,

V., and Narayanan, V. 2008. Synthesis, electrochemical, catalytic and antimicrobial activities of

novel unsymmetrical macrocyclic dicompartmental binuclear nickel (II) complexes. Polyhedron

27(7): 1867-1874.

16. Jamuna, K., Reddy, D.H.K., Kumar, B.N., Venkata Ramana, D.K., and Seshaiah, K. 2011.

Synthesis, characterization and biological activity of Cu(II) and Ni(II) complexes of 3-hydroxy-

4- (pyridine-2-yl-methylene amino) benzoic acid. Orient J Chem 27(3): 1141-1147.

17. Patel, B., Haswell, S.J., and Grzeskowiak, R. 1989. Flow injection flame atomic absorption

spectrometry system for the pre-concentration of vanadium (V) and characterization of vanadium

(IV) and (V) species. J Anal At Spectrom 4: 195-198.

18. Fiabane, A.M., Touche, M.L.D., and Williams, D.R. 1978. Metal-ligand complexes involved in

rheumatoid arthritis-III: Bovine serum albumin-copper (II), zinc(II) and lead(II) interactions

investigated using potentiometric analysis and molecular filtration. Polyhedron 40(6): 1201-1207.



19. El-Sirafy, I.H., and El-Boray, N.A. 1985. Deflection of a clamped eccentric circular ring plate and

an infinite plate with two'clamped circular holes. Proc Indian Natl Sci Acad B Biol Sci 51(2):

407-418.

20. Sorenson, J.R.J. 1976. Copper chelates as possible active forms of the antiarthritic agents. J Med

Chem 19(1): 135-148.

21. Willard, H.H. and Greathouse, L.H. 1917. The colorimetric determination of manganese by

oxidation with periodate. J Am Chem Soc 39 (11): 2366-2377.

22. Macdonald, A.M.G., and Sirichanya, P. 1969. The determination of metals in organic compounds

by oxygen-flask combustion or wet combustion. Microchem J 14(2): 199-206.

23. Ramsay, J.A., Brown, R.H.J., and Croghan, P.C. 1955. Electrometric titration of chloride in small

volumes. J Exp Biol 32: 822-829.

24. Tabatabai, M.A. 1974. A rapid method for determination of sulfate in water samples. Environ Lett

7(3): 237-243.

25. Sacconi, L., Ciampolini, M., and Nardi, N. 1964. Investigation on the occurrence of tetrahedral

forms of substitued bis(N-alkylsalicylaldimino)nickel(II) complexes. J Chem Soc 86(5): 819-823.

26. Pal, S., Mareddy, J., and Devi, N.S. 2008. High speed synthesis of pyrazolones using microwave-

assisted neat reaction technology. J Braz Chem Soc 19(6): 1207.

27. Ghammamy, S. 2012. The synthesis, characterization and theoretical study of nano

tetrabuthylammonium trichloroiodoaluminate (III). Orbital: Electronic J Chem 4(3).

28. Ito, K., and Ito, T. 1958. Magnetic moments of copper (II) complexes. Aust J Chem 11(4): 406-

414.

29. Joshi, K.C., Pathak, V.N., and Bhargava, S. 1977. Studies in fluorinated β-diketones and related

compounds-IV: Synthesis and spectral studies of some new fluorinated β-diketones and their

copper chelates. J Inorg Nucl Chem 39(5): 803-810.

30. Shirin, Z., and Mukherjee, R.M. 1992. Synthesis, spectra and electrochemistry of ruthenium (III)

complexes with cage-like Schiff-base ligands. Polyhedron 11(20): 2625-2630.

31. Singh, A.K., and Sharma, U.N. 2002. Studies on Co2+

, Ni2+

and Cu2+

complexes with Schiff bases

derived from Benzil Monohydrazone. Asian J Chem 14: 1221-1224.

32. Wester, D., and Palenik, G.J. 1973. Synthesis and characterization of novel pentagonal

bipyramidal complexes of iron(II), cobalt(II), and zinc(II). J Am chem Soc 95(19): 6505-6506.

33. Temel H. 2004. Synthesis and spectroscopic studies of new Cu(II), Ni(II), VO(IV) and Zn(II)

complexes with N, N′-bis(2-hydroxynaphthalin-1-carbaldehydene)-1,2-bis-(o-aminophenoxy)

ethane. J Co-ord Chem 57(9): 723-729.

34. Raman, N., Kulandaisamy, A., Thangaraja, C., and Jeyasubramanian, K. 2003. Redox and

antimicrobial studies of transition metal (II) tetradentate Schiff base complexes. Transition Met

Chem 28: 29-36.



35. Raman, N., Ravichandran, S., and Kulandaisamy, A. 2002. Synthesis of 2,4-dinitrophenyl

hydrazone derivatives of Co(II), Cu(II) and Ni(II) complexes of [beta]-diketones [beta]-ketoesters

and their antimicrobial activities. Asian J Chem 14(3): 1261-1264.

36. Kumar, P.P., Prasad, Y.R., Kumar, N.R., and Sridhar, S. 2008. Synthesis and antimicrobial

activity of 6,7,8,9-tetrahydro-5(H)-5-nitrophenylthiazolo[2,3-b]-quinazoline-3(2H)-one

derivatives. Asian J Chem 20(7): 5161-5165.

37. Kumar, U., and Chandra, S. 2010. Synthesis, characterization and in vitro antifungal screening of

Manganese (II) and Copper (II) complexes of Hexaaza [N6] macrocyclic ligand. J Nepal Chem

Soc 25: 46-52.

38. Shrivastava, S., Kumar, A., Pandey, Y., and Dikshit S.N. 2009. Synthesis, spectral and biological

studies of Cu(II), Zn(II) and Cd(II) complexes with Schiff base ligand. Asian J Chem 21(8):

6228-6232.

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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The authors declare that they have no conflict of interests regarding the publication of this paper.

Copyright © 2015 by authors. This is an open access article distributed under the Creative Commons Attribution License, which

permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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