SYNTHESIS, CHARACTERIZATION AND ANTIBACTERIAL

www.wjpps.com │ Vol 10, Issue 9, 2021. │ ISO 9001:2015 Certified Journal │

2059

Ajibulu et al. World Journal of Pharmacy and Pharmaceutical Sciences

SYNTHESIS, CHARACTERIZATION AND ANTIBACTERIAL

ACTIVITY OF SCHIFF BASE, N, N1- BIS(4-NITROBENZYLIDENE)

ETHYLENEDIAMINE, METAL(II) COMPLEXES

K. E. Ajibulu*, A. E. Okoronkwo and J. B. Owolabi

Department of Chemistry, Federal University of Technology, P.M.B.704 Akure, Ondo State,

Nigeria.

ABSRACT

The Schiff base ligand, N,N1-bis(4-nitrobenzylidene) ethylenediamine,

has been synthesized by stirring ethylenediamine and 4-

nitrobenzaldehyde in ratio 1:2 at room temperature. The ligand was

characterized using (FT-IR, UV-vis) spectroscopies, (1H,

13C) NMR

spectrum, Mass Spectrum, TGA/DTA and magnetic moments.

Matal(II) complexes of the ligand were synthesized in a ratio of 1:2,

M:L, and characterized. From elemental analysis data, the metal

complexes formed had the general formulae [M(L)2], where L = Schiff

base ligand (C16H14N4O4) and M = Mn, Ni and Co. On the basis of FT-

IR, and NMR data “N” donor atoms of the Schiff base ligand

participated in coordination with metal (II) ions, and thus, a four

coordinated tetrahedral geometry for the complexes of Mn and Ni while six coordinated

octahedral geometry proposed for Co respectively. The free ligand and its metal complexes

have been screened for biological activity against Gram-positive and Gram-negative bacteria.

KEYWORDS: Schiff base, ethylenediamine, antibacterial, metal(II) complex.

1. INTRODUCTION

The condensation of an amine with aldehyde or ketone, forming what is called a Schiff base

is one of the oldest reactions in chemistry.[1-2]

Schiff base ligands coordinate to a metal

through the imine nitrogen and another group, usually oxygen.[3-7]

Bidentate Schiff bases with

N,N donor atoms are well known to coordinate with various metal ions and have attracted a

great deal of interest in recent years due to their rich coordination chemistry.[8-10]

Schiff base

WORLD JOURNAL OF PHARMACY AND PHARMACEUTICAL SCIENCES

SJIF Impact Factor 7.632

Volume 10, Issue 9, 2059-2072 Review Article ISSN 2278 – 4357

*Corresponding Author

K. E. Ajibulu

Department of Chemistry,

Federal University of

Technology, P.M.B.704

Akure, Ondo State, Nigeria.

Article Received on

24 July 2021,

Revised on 13 Aug. 2021,

Accepted on 02 Sept. 2021,

DOI: 10.20959/wjpps20219-19563


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ligands are potentially capable of forming stable complexes with metal ion.[11-15]

The

azomethine (-HC=N-) linkage present in Schiff base ligand and its metal(II) complexes show

a wide range of biological activity and are of useful industrial application.[16-22]

In this article,

we present the synthesis, characterization and thermal analysis of Co(II), Ni(II), and Mn(II)

complexes containing bidentate Schiff base ligand, N,N1-bis(4-nitrobenzylidene)

ethylenediamine, and to examine their biological activity against Escherichia coil,

Staphylococcus aureu, Klebsiella pnuemoniae and bascillus substillis

2. EXPERIMENTAL

2.1 MATERIALS AND METHODS

The chemicals and solvents used in this research work were of analytical grade source from

Sigma-Adrich Chemical Company. Synthesis of Schiff Base ligand was carried out in pure

solvent. FT-IR spectra of synthesized compounds (in a KBr) were recorded in

400-500/400 cm-1

region on infrared spectrometer Varian 660 MidIR Dual/MCT/DTGS

Bundle with ATR. The 1H and

13C NMR spectra of the Schiff base ligand are recorded in

deuterated DMSO (Internal Standard TMS) on Bruker spectrometer. The electronics spectra

of the synthesized compounds were recorded on a Spectrumlab 752S spectrophotometer in

the 0-400, 400-900 range for ligand and complexes. Magnetic susceptibility measurements of

the metal complexes were determined on Gouy balance at room temperature using

Swissmake-H-1640 with maximum capacity 80g and precision ±0.01 mg. Melting point were

recorded on a gallenkamp apparatus and are uncorrected. The TGA/DTG were recorded on

Shimadzu TGA - Q50 thermo balance. For each sample analysed by TGA the run starts in

Nitrogen and ramps the temperature up to 8000C, 10

0C min

-1. The synthesized compounds

were screened in vitro for their antibacterial activities against Gram positive and Gram

negative bacterials using the plate diffusion method.[23]

2.2 Synthesis of Schiff Base Ligand: N, N1-bis(4 nitrobenzylidene) ethylenediamine

The ligand (L) (Scheme 1) was prepared according to the literature.[23]

Ethylenediamine

(0.012mol, 0.7g) with 4-nitrobenzaldehyde (0.002mol, 3.54g) in a 50ml round bottom flask

was stirred in 20ml ethanol at room temperature for 3 hours, two drops of conc. H2SO4 was

added to the mixture to adjust its PH to ≈ 6. The resulting milk coloured precipitate formed

was separated by filtration and purified by recrystalization from ethanol (and dried overnight

in air). Yield: 76%, 3.2lg, colour: milk, m.p: 189– 2010C. Elemental analysis for C16H14N4O4

(FW = 326.31) found: C, 58.62%; H, 4.27%; N,17.12% calculated: C, 58.89%; H, 4.29%; N,


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17.17%. MW:326g. FT-IR (KBr, disc cm-1

): 1118v(C-N), 1635.3 v(HC=N), UV-Vis

(acetonitrite) & max (nm) 275, 298. 1HNMR (ppm d6 – DMSO, 400 MHZ): 8.6(S, 1H, CH =

N), 8.4 (S, 2H, N-CH2), 8.0 – 8.4(Ar H). 13

CNMR (ppmd6 - DMSO):161(HC = N), 129-

124(Ar, C=C). MS: m/z 326[m+ + 1].

2.3. Synthesis of the Schiff Base Metal Complexes

The Schiff base Metal (II) Complexes (Scheme 1) were prepared by reacting the Schiff base

with the metal (II) ions according to the literature methods.[23, 24]

Metal (II) salts of Co, Ni and Mn were used to complex the ligand, 0.02mole of Schiff base

was dissolved in 20ml ethanol in around bottom flask. To this solution, 0.01 mole of metal

salt solution was added. The mixture was magnetically stirred and reflux for 3 hours at

500C. The precipitate formed was filtered, washed with cold water to remove unreacted

Schiff base ligand and its metal (II) Salts.

O2N CH O + H2N NH2+ CH NO2O

Stir in EtOH, rt. for 3hrs

O2N CH N N CH NO2

Refluxed in EtOH

for 31/2 hrs

O2N CH N N CH NO2

O2N CH N N CH NO2

M

= =

==

= =

==

MX.nH2O

Where M = Co (II), Ni (II) and Mn (II).

Figure 1: Synthesis of the Schiff base ligand and its metal (II) complexes.

2.3.1. Mangnese (II) Complex: Yield, 66.5%, M.W 821g, Colour: deep brown, m.p = 3100C.

Elemental analysis data for C32H30SMnN8O13 found: C, 46.53%; H, 3.63%; N, 13.61%

calculated: C, 46.77%; H, 3.60%; N, 13.64%. FT-IR (KBr Disc Cm-1

): 1632 v(HC=N), 1113

v(C-N), 527v(M-N), UV-Vis (acetonitrite) λ max (nm) 336, 400. MS: m/z 822[M+ + 1]


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2.3.2. Cobalt (II) complex: Yield: 55.2% Colour: Indian Red, M.P: ˃3000C, MW =

780g. Elemental analysis data for C32H28 Cl2CoN8O8 found: C, 49.16%; H, 3.46%; N, 14.38%

calculated: C, 49.23%; H, 3.59%, N, 14.36%. FTIR: 1597 v(HC = N), 588.08 v(H20), 542.50

v(M-N), 1132 v(C-N). UV-vis (acetonitrite) λ max (nm), 481, 611, 662. MS: m/z 780[M+ +

1].

2.3.3. Nikel (II) Complex: Yield: 68.8%. Colour: Orange green, M.p: 2650C, MW = 807g. El

emental analysis data for C32H28SNiN8O12 found: C, 47.52%; H,3.45%;N, 13.36% calculated:

C, 47.58%; H, 3.47; N, 13.88%. FT-IR: 1601 v(HC=N), 1130 v(C-N) 521.13v(M-N). UV-

Vis (acetonitrite) λ max (nm), 506, 612, 721.MS: m/z 807[M+ + 1].

2.4 ANTIMICROBIAL ACTIVITIES

Susceptibility of two Gram-positive and two Gram-negative bacteria isolate to metal

complexes and ligands was determined following the BSAC Diffusion Method for

Antimicrobial Susceptibility Testing Version 9.1.[25]

This test was carried out to determine

the antimicrobial ability of the metal complexs and ligands to inhibit the growth of the test

bacteria isolates that were collected from Microbiology Department, Adekunle Ajasin

University, Akungba Akoko. The plate diffusion technique was used for the antibiotic

sensitivity test. Overnight cultures of the organisms were swabbed on sterile Muller Hilton

solidified Agar plates using sterile swab sticks. 8mm sized cork borer was used to bore hole

on the agar surface at equidistance. The well was filled with 50 μg/ml of metal complexes

and ligands, Amoxicillin was used as positive control while 30% DMSO used in diluting and

dissolving into solutions as negative control. All the plates were incubated at 370C to 24

hours. The zones of inhibition generated by the antibiotics were measured to the nearest

millimetres (mm) and interpreted as sensitive (S), intermediate (I), and resistant (R). The

zones of inhibition were measured and interpreted according to.[23]

3.0 RESULT AND DISCUSSION

The Schiff base ligand in this study was first synthesized by.[8]

using the reflux method. In

this research, the ligand was prepared using room temperature method. The Schiff base

ligand is soluble in DMSO. The metal complexes are colured solids which are stable in air.

The complexes are soluble in DMSO and water.

The melting points of the complexes were higher than that of the Schiff base ligand,

indicating that the complexes are more stable than the ligand. The chemical equation showing


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the preparation of the Schiff base ligand and its metal (II) complexes are represented in

scheme 1.

3.1 FT-IR Spectral Analysis. The formation of Schiff base ligand and metal complexes was

determined by comparing the FT-IR spectrum of the free ligand with the spectra of the metal

(II) complexes. The stretching frequency of the azomethine HC=N bound, v(C-N) were

observed at 1635 and 1188 cm-1

for the free ligand. The HC=N stretching frequencies in

metal (II) complexes were observed at 1597, 1601 and 1632cm-1

for Cobalt(II), Nikel(II) and

Maganese(II), respectively, shift to lower wave members. This indicated coordination of

Schiff base through the azomethine nitrogen.[8, 24]

The appearance of weak band in the region

529-588cm-1 attribute to v(M-N).[8, 27]

confirmed complexation. This shows that the Schiff

base ligand coordinated to the metal via “N” atoms.

3.2 NMR Spectral Analysis. The 1H and

13C NMR spectra of the Schiff base ligand and its

metal (II) complexes were recorded in DMSO-d6 as shown in figure 1 (a) and (b). The 1H

NMR spectrum of the Schiff base showed a single peak at δ=8.6ppm corresponding to the

azomethine proton (HC=N-) confirmed the formation of Schiff base during condensation

reaction. The observed peak at δ = 161.24ppm in the 13

C NMR specturum was further proof

that the ligand was successfully synthesized.[4,27]

3.3 ELECTRONIC SPECTRAL ANALYSIS

The electronic spectral data of the Schiff base ligand and its metal (II) complexes are given in

the experimental section. The Schiff base ligand exhibit two bands at 275 and 298nm

respectively.

(a) (b)

Fig. 1: (a) 1H NMR spectrum of ligand (L

1), (b)

13C NMR spectrum of ligand (L

1)


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The band at 275nm is assigned to the π–π* in benzene.[24]

The band appearing at 298nm is

assigned to n - π* transition of nonbonding electrons present on the nitrogen of the

azomethine group (C = N); upon complexation, π–π* transition of ligand shift to a longer

wavelength.

In Co(II) complex, three bands were observed at 481, 611 and 662.nm. This observed

transition are due to d-d transition assigned to 4T1(g)(F)

4T2(g)(F)(v1),

4T1(g)(F)

4A2(g)(F) (v2),

4T1(g)(F)

4T1(g)(P)(V3), respectively suggesting octahedral geometry

around the Co(II) ion.[27-29]

The electronic spectra of Ni(II) complex exhibited three bands, 506, 612,and 721nm

respectively. This bands are assigned to transition, 3A2(F)

3T1(F)(v1),

3A2(F)

3T2(F)(v2),

3A2(F)

3T1(P)(V3).

The observed magnetic susceptibility, 3.78 B.M (normal range for tetrahedral complexes is

3.7-4.0) is an indicative of tetrahedral geometry.[30]

Electronic spectra of Mn(II) complexes

gives two bands, 336, 400. The band 336nm may be attributed to ligand-metal charge

transfer, while 400nm band is assigned to transition, 6A1 4T2 which suggest tetrahedral

geometry around Mn(II) ion.[28, 31, 32]

3.4 CONDUCTIVITY MEASUREMENT

The molar conductivity of the synthesised compounds were measure at room temperature in

10-3

M water, acetone and methanol. The values of molar conductivity of the synthesized

compounds range between 119-127 Ohm-1

.Cm2. Mol

-1 for Ni(II) and Mn(II) complexes

indicating their electrolytic nature, while 85 Ohm-1

.Cm2.Mol

-1 for Co(II) indicating

nonelectro lytic nature.[33]

It suggested that there were anions present outside the coordination

sphere of Ni(II) and Mn(II) complexes.

3.5 THERMAL ANALYSIS

Thermal data and metal ligand (L) of the complexes are given in Table 1. The analysis

of TG/DTG curves of the ligand Fig. 2, showed that thermal decomposition occurs through

four steps. The first degradation step began at 20oC-152

oC may be accounted for loss of

(CH2-CH2), assigned to 8.2%(Obs.), 8.6%(Calc.). This step combined with two different

processes, the first is exothermic with TDTG at 80oC and the second endothermic process with

TDTG at 151oC. The second step in the temperature range 152

oC-394

oC can be attributed to


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the loss of (C6H4) group, assigned to 23.5% (Obs.), 23.31% (Calc.). The degradation is

exothermic process (TDTG) peak at 165oC. The third decomposition at 394

oC-600

oC broad

exothermic process (TDTG) peak at 449oC and broad endothermic (TDTG) peak at 559

oC is

attributed to loss of NO2 group assigned to 15.4%(Obs.), 14.11%(Calc.). The forth

degradation in the temperature range of 670oC-800

oC with sharp-long exothermic (TDTG)

peak at 750oC is attributed to the loss of [C6H4, NO2, (CH=N)2], assigned to 51.40% (Obs.),

48.62% (Calc.).

(a) (b)

(c) (d)

Figure 2: (a) TG curve of Ligand L (b) TG curve of complex L(Co) (c) TG curve of

complex L(Mn) (d) TG curve of complex L(Ni)

The analysis studies of TG/DTG curve [Ni(L)2]

complex, Figure 2(d) revealed that thermal decomposition occurs through three steps. The

first step observed at 20oC-175

oC with endothermic effect TDTG at 47

oC, 9.2% Obs.),

9.04% (Calc.) mass loss due to removal of [CH2, 4H, NO2]. The second step may be

accounted for the loss of [(C6H6)2, (NO2)2] at temperature range 175oC-349

oC with two

processes, sharp endothermic (TDTG) peak at.


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Table 1: TG/DTG Data of Ligand and its Complexes with Decomposition Steps.

Compound Step

Temp.

Range

(oC)

DTG

Max

(oC)

Thermal

Effect

Mass loss.

Cal. (Obs)

(%)

Assignment Metallic

Residue

L

1st

2nd

3rd

4th

20 – 152

152 – 394

394 – 600

600 – 800

80

165

449

670

Exo

Exo

Exo

Exo

8.60 (8.20)

23.31 (23.50)

14.11 (15.40)

48.62 (51.40)

CH2 = CH2

C6H6

NO2

C6H4, NO2, (CH = N)2

Ni(L)2

1st

2nd

3rd

20 – 175

175 – 349

369 – 565

47

275

400

Endo

Endo

Exo

9.04 (9.20)

34.32 (34.5)

33.80 (33.60)

CH2, 2H, NO2

(C6H6)2, (NO2)2

(CH=N)2, (CH2 = CH2,), C6H4

NiO

Mn(L)2

1st

2nd

3rd

47 – 150

150 – 327

327 – 500

98

228

400

Exo

Exo

Endo

14.2 (14.14)

28.01 (27.8)

40.02 (40.80)

CH2, 2H, (CH2=N)2,

H2O, C2H42(C6H4), NO2

(C6H4)2, (NO2)2

MnO

Co(L)2

1st

2nd

3rd

4th

22 – 170

170 – 352

294 – 598

598 – 800

47

190

400

___

Endo

Endo

Endo

___

15.47 (15.80)

18.0 (17.80)

16.59 (17.20)

____

CH2, 4H CH2 = CH2, (NO2)2

(C6H4CH=N)2, NO2

C4H6, NO2

CoO

(a) (b)

(c) (d)

Fig. 3: (a) Mass spectrum of ligand (L1), (b) Mass spectrum of complex Ni(L2), (c) Mass

spectrum of complex Co(L2), (d) Mass spectrum of complex Mn(L2).


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200oC and broad exothermic (TDTG) peak at 275

oC assigned to 34.5% (Obs.), 34.32% (Calc.).

The third decomposition step involves the removal of [(CH=N)2, (CH2-CH2)2, C6H4] at

369oC-565

oC with sharp exothermic effect (TDTG) peak at 400

oC, 33.6% (Obs.), 33.8%

(Calc.) mass loss. The possible remaining products (theoretically calculated 25.4%) may be

assigned to Ni(II) Nitrobenzene residues [C6H4O-NiON]. Lack of mass lose due to water

molecule confirms absence of water molecule in the environment of the complex.[4, 27]

The Mn(II) complex degrade in three steps Figure 2(c). The first loss in temperature range

47oC-150

oC, with broad exothermic process (TDTG) peak at 98

oC, may account for the loss

[H2O, (CH=N)2, C2H4] assigned to 14.2% (Obs.), 14.14% (Calc.) mass loss. The second

decomposition is characterized by three short exothermic effects with (TDTG) peaks at 170oC,

198oC, 300

oC and two short endothermic effects with (TDTG) peaks at 176

oC, 228

oC with

mass loss at 150oC-327

oC assigned to 27.8% (Obs.), 28.01% (Calc.). The third step involved

the removal of [(C6H4)2 (NO2)2] at 327oC-500

oC with long-sharp endothermic effect, (TDTG)

peak at 400oC, assigned to 40.8% (Obs.), 40.02% (Calc.). The final decomposition at 500

oC-

800oC corresponded to the formation of metal oxide of [C4H6N2] residue.

The Co(II) complex degrade in three steps Figure 2. The first step at 22oC-170

oC may

account for loss of [CH2, 4H, CH2=CH2, (NO2)2] of short endothermic effect with (TDTG)

peak at 47oC and broad exothermic with (TDTG) peak at 148

oC, assigned to 15.8% (Obs.),

15.47% (Calc.). Second decomposition step was recorded at temperature range of 170oC-

352oC, 17.8% (Obs.), 18.0% (Calc.) mass loss, may be assigned to decomposition of [(C6H4-

CH=N)2] and [NO2] parts, with weak endothermic and exothermic effect (TDTG) peak at

1900C and 294

0C. The third decomposition at 294

0C - 598

0C with long-sharp endothermic

process (TDTG) peak at 4000C account for loss [C4H6, NO2], assigned to 17.2% (Obs.),

16.59% (Calc.). The last step of pyrolysis at 598oC-800

oC account for loss of organic moiety

leaving CoO as residue.[8]

The results of thermal decomposition related to Co(II) and Ni(II) complexes were in

agreement with Irving-Williams series. The order of stability, Co(II) < Ni(II).[4]

3.6 Mass Spectra

The recorded mass spectrum of ligand and its metal (II) complexes with molecular ion peak

have been used to confirm the proposed structures.


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3.6 Antimicrobial Activity. The antimicrobial activity test were conducted according to the

standard procedure.[2]

The result are shown in Table 2.

All the bacteria showed an intermediate to sensitive reaction to all the metal complexes and

the ligand tested. The inhibitory ability of the Schiff base ligand and its metal (II) complexes

were compared to that of known standard antimicrobial drug, Amoxicillin, Ligand (L) and

Mn(II) showed maximum inhibition zone against Escherichia coil while Ni(II) complex

showed maximum inhibition zone against Klebsiella pnuemoniae. The Co(II) complex had

the highest activity against Staphylococcus aureu.

Table 2: Antibacterial sensitivity test of Schiff base ligand and its metal (II) complexes.

Name of

organism L(mm) Ni(mm) Mn(mm) Co(mm) Amoxicillin(mm)

30%

DMSO(mm)

Klebsiella

pnuemoniae

22.00

21.00

19.00

18.00

19.00

16.00

14.00

16.00

15.00

14.00

12.00

13.00

30.00

27.00

28.00

0.00

Staphylococcus

aureus

16.00

15.00

16.00

14.00

13.00

13.00

14.00

14.00

12.00

13.00

15.00

14.00

35.00

32.00

33.00

0.00

Escherichia

coil

28.00

27.00

28.00

18.00

17.00

16.00

16.00

15.00

17.00

18.00

17.00

17.00

34.00

31.00

34.00

0.00

Bacillus

subtillis

24.00

23.00

21.00

17.00

16.00

17.00

14.00

13.00

14.00

15.00

14.00

13.0

32.00

31.00

32.00

0.00

Sensitive (S) ≥ 14, Intermediate (I) 13≤ 9 and resistant (R) ≤ 9

Name of organism L(mm) Ni(mm) Mn(mm) Co(mm) Amoxicillin(m

m)

30%D

MSO

Klebsiella pnuemoniae 20.67±1.528b 17.67±1.528

b 15.00±1.000

a 13.00±1.000

a 28.53±1.528

a 0

Staphylococcus aureus 15.67±0.577a 13.33±0.577

a 13.33±1.155

a 14.00±1.000

a 33.33±1.1528

b 0

Escherichia coil 27.67±1.0.577c 17.00±1.000

b 16.00±1.000

b 17.33±0.577

b 33.00±1.732

b 0

Bacillus subtillis 22.67±1.528b 16.67±0.577

b 13.67±0.577

a 14.00±1.000

a 31.67±0.577

b 0

Value are mean ± standard deviation of three replicates. Values in the same column with

different superscript are significantly different at P < 0.05

4.0 CONCLUSIONS

The Schiff base ligand N, N1-bis(4-nitrobenzylidene) ethylenediamine (C16H14N4O4) and its

metal(II) complexes of Co(II), Ni(II) and Mn(II) were successfully synthesized and

characterised. The Schiff base ligand coordinated to the metal (II) ion through azomethine

nitrogen resulting to the formation of stable complexes, two tetrahedral Ni(II), Mn(II) and


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one (Co(II)) octahedral geometry. The proposed geometries were based on the electronic

spectra and their molar conductivity. Ni(II) and Mn(II) were found to be electrolytic while

Co(II) non electronic in nature. All the tested compounds showed significant effects on the

tested organisms but, the Schiff base ligand exhibited better antimicrobial properties than the

metal (II) complexes. The TG/DTG analysis shows that the ligand and its complexes are

stable.

ACKNOWLEDGMENT

The authors wish to appreciate the Laboratory Scientists at the Department of Chemistry,

Federal University of Technology Akure for their support during this research work.

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