9
Research Journal of Chemical Sciences ______________________________________________ ISSN 2231-606X Vol. 5(7), 20-28, July (2015) Res. J. Chem. Sci. International Science Congress Association 20 Synthesis, Characterization and Antimicrobial screening of some Azo compounds derived from Ethyl vanillin Pagariya S.K. * , Pathade R.M. and Bodkhe P.S. Department of Chemistry, Vidyabharati Mahavidyalaya, Amravati, 444602, INDIA Available online at: www.isca.in, www.isca.me Received 19 th June 2015, revised 30 th June 2015, accepted 17 th July 2015 Abstract Azo compounds were synthesized in excellent yield by diazotization of some substituted aromatic amines using NaNO 2 and concentrated HCl followed by coupling with ethyl vanillin in alkaline medium. These azo compounds were characterized by FTIR and H 1 NMR spectroscopic technique and have been tested against the growth of five gram positive and negative microorganisms in order to assess their antimicrobial activity. Keywords: Azo compounds, ethyl vanillin, diazotization, antimicrobial activity. Introduction Azo compounds are mostly used as dyes due to its various applications in the fields such as textile fibres, colouring of different materials, biomedical studies and organic synthesis 1-2 . The azo dyes containing azo linkages have advanced applications in high technology areas like lasers 3 , LCD color filters 4 . In addition to this, azo dyes were reported to have variety of biological applications like antineoplastics, antidiabetics, antiseptics, anti-inflammatory and other useful chemotherapeutic agents 5-8 . Scarlet red and diamazon are the most commonly used azo dyes which are antiseptics. Several azo compounds derived from thymol 9 , aspirin 10 , paracetamol 11 , m-cresol 12 , resorcinol 13 and vanillin 14 moieties have been frequently reported and exhibit excellent biological properties. In the present work, we have synthesized four azo compounds derived from ethyl vanillin and characterized by FTIR and H 1 NMR spectral technique. The antimicrobial potential of synthesized azo compounds of ethyl vanillin has been tested against the growth of five gram positive and negative microorganisms using agar well diffusion method. Material and Methods In the present synthesis, chemicals and reagents used were of analytical grade, Merck and Alfa Aesar Company Ltd. The azo compounds were characterized by FTIR and H 1 NMR spectroscopic techniques. The Perkin-Elmer spectrum One FTIR instrument was used for characterization of IR spectra in the form of KBr pallet. Bruker Avance II 400 MHz NMR spectrometer was used for characterization of H 1 NMR spectra of azo compounds using CDCl 3 as a solvent and TMS as an internal standard. The purity of all the compounds was checked by thin layer chromatography and were recrystalised from hot ethanol. The melting points were measured by open capillary method and they are uncorrected. Procedure for the synthesis of azo compounds 9-10: Aromatic amines (0.01 mole) were mixed with 2.5 ml of concentrated HCl. To this resultant solution, 25 gm of crushed ice and 2.5 ml of NaNO 2 (4N) was added with constant stirring. The temperature of the reaction mixture was kept constant up to 0- 5 0 C. The diazonium salt solution prepared was added to the alkaline solution of ethyl vanillin drop by drop with constant stirring for 10-25 minutes at constant temperature of 5-10 0 C. The colored precipitate given out was filtered and washed with water number of times. The colored product was recrystallised from hot ethanol. The general reaction scheme for synthesis of azo compounds of ethyl vanillin is shown in figure-1. Antimicrobial Activity: The azo compounds 1a-d were analysed for their antibacterial activity against five gram positive and negative pathogens viz. Escherichia coli, Pseudomonas aeroginosa, Salmonella typhi, Bacillus subtilis and Staphylococcus aureus by using agar well diffusion method 15-16 . These compounds were mixed in DMSO to form solutions of concentration 1mg/ml. Sterile discs were dipped in this solutions, dried it and placed on nutrient agar plates spreaded with the bacteria. The plates were further incubated for 24 to 48 hours at 37 0 C and the diameters of zones of inhibition were measured in millimeter. Results and Discussion The data of synthesized azo compounds of ethyl vanillin (i.e. symbols, compounds name, molecular formulae, molecular weights, melting points and percentage yield) are given in table- 1. The FTIR and H 1 NMR spectroscopic data of synthesized azo compounds are illustrated in table-2 and are shown in figure-6 to 13. A total four azo compounds of ethyl vanillin have been synthesized, recrystalised and used separately to study its antimicrobial activity against five gram positive and negative microorganism’s viz. Escherichia coli, Pseudomonas aeroginosa, Salmonella typhi, Bacillus subtilis and

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Research Journal of Chemical Sciences ______________________________________________ ISSN 2231-606X

Vol. 5(7), 20-28, July (2015) Res. J. Chem. Sci.

International Science Congress Association 20

Synthesis, Characterization and Antimicrobial screening of some Azo

compounds derived from Ethyl vanillin

Pagariya S.K.*, Pathade R.M. and Bodkhe P.S.

Department of Chemistry, Vidyabharati Mahavidyalaya, Amravati, 444602, INDIA

Available online at: www.isca.in, www.isca.me Received 19th June 2015, revised 30th June 2015, accepted 17th July 2015

Abstract

Azo compounds were synthesized in excellent yield by diazotization of some substituted aromatic amines using NaNO2 and

concentrated HCl followed by coupling with ethyl vanillin in alkaline medium. These azo compounds were characterized by

FTIR and H1

NMR spectroscopic technique and have been tested against the growth of five gram positive and negative

microorganisms in order to assess their antimicrobial activity.

Keywords: Azo compounds, ethyl vanillin, diazotization, antimicrobial activity.

Introduction

Azo compounds are mostly used as dyes due to its various

applications in the fields such as textile fibres, colouring of

different materials, biomedical studies and organic synthesis1-2

.

The azo dyes containing azo linkages have advanced

applications in high technology areas like lasers3, LCD color

filters4. In addition to this, azo dyes were reported to have

variety of biological applications like antineoplastics,

antidiabetics, antiseptics, anti-inflammatory and other useful

chemotherapeutic agents5-8

. Scarlet red and diamazon are the

most commonly used azo dyes which are antiseptics. Several

azo compounds derived from thymol9, aspirin

10, paracetamol

11,

m-cresol12

, resorcinol13

and vanillin14

moieties have been

frequently reported and exhibit excellent biological properties.

In the present work, we have synthesized four azo compounds

derived from ethyl vanillin and characterized by FTIR and H1

NMR spectral technique. The antimicrobial potential of

synthesized azo compounds of ethyl vanillin has been tested

against the growth of five gram positive and negative

microorganisms using agar well diffusion method.

Material and Methods

In the present synthesis, chemicals and reagents used were of

analytical grade, Merck and Alfa Aesar Company Ltd. The azo

compounds were characterized by FTIR and H1 NMR

spectroscopic techniques. The Perkin-Elmer spectrum One

FTIR instrument was used for characterization of IR spectra in

the form of KBr pallet. Bruker Avance II 400 MHz NMR

spectrometer was used for characterization of H1 NMR spectra

of azo compounds using CDCl3 as a solvent and TMS as an

internal standard. The purity of all the compounds was checked

by thin layer chromatography and were recrystalised from hot

ethanol. The melting points were measured by open capillary

method and they are uncorrected.

Procedure for the synthesis of azo compounds9-10:

Aromatic

amines (0.01 mole) were mixed with 2.5 ml of concentrated

HCl. To this resultant solution, 25 gm of crushed ice and 2.5 ml

of NaNO2 (4N) was added with constant stirring. The

temperature of the reaction mixture was kept constant up to 0-

50C. The diazonium salt solution prepared was added to the

alkaline solution of ethyl vanillin drop by drop with constant

stirring for 10-25 minutes at constant temperature of 5-100C.

The colored precipitate given out was filtered and washed with

water number of times. The colored product was recrystallised

from hot ethanol. The general reaction scheme for synthesis of

azo compounds of ethyl vanillin is shown in figure-1.

Antimicrobial Activity: The azo compounds 1a-d were

analysed for their antibacterial activity against five gram

positive and negative pathogens viz. Escherichia coli,

Pseudomonas aeroginosa, Salmonella typhi, Bacillus subtilis

and Staphylococcus aureus by using agar well diffusion

method15-16

. These compounds were mixed in DMSO to form

solutions of concentration 1mg/ml. Sterile discs were dipped in

this solutions, dried it and placed on nutrient agar plates

spreaded with the bacteria. The plates were further incubated for

24 to 48 hours at 370C and the diameters of zones of inhibition

were measured in millimeter.

Results and Discussion

The data of synthesized azo compounds of ethyl vanillin (i.e.

symbols, compounds name, molecular formulae, molecular

weights, melting points and percentage yield) are given in table-

1. The FTIR and H1 NMR spectroscopic data of synthesized azo

compounds are illustrated in table-2 and are shown in figure-6

to 13. A total four azo compounds of ethyl vanillin have been

synthesized, recrystalised and used separately to study its

antimicrobial activity against five gram positive and negative

microorganism’s viz. Escherichia coli, Pseudomonas

aeroginosa, Salmonella typhi, Bacillus subtilis and

Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X

Vol. 5(7), 20-28, July (2015) Res. J. Chem. Sci.

International Science Congress Association 21

Staphylococcus aureus. The data on antimicrobial activity of

azo compounds of ethyl vanillin 1a-d against five pathogens are

presented in table-3. From the results it was observed that the

azo compounds of ethyl vanillin have showed miraculous

antibacterial potential against all five pathogens. The compound

1a showed 10.4 and 9.6 mm zones of inhibition against the test

pathogens Escherichia coli and Staphylococcus aureus

respectively as shown in figure-2 and do not showed any

inhibitory action against Salmonella typhi, Pseudomonas

aeroginosa and Bacillus subtilis. The azo compound 1b showed

10.6, 12.7, 11.8 and 9.8 mm zones of inhibition against the test

pathogens Escherichia coli, Salmonella typhi, Bacillus subtilis

and Staphylococcus aureus respectively shown in figure-3 but

do not showed any inhibitory action against Pseudomonas

aeroginosa. The azo compound 1c showed 10.3, 13.1, 13.5 and

12.8 mm zones of inhibition against the pathogens Escherichia

coli, Salmonella typhi, Bacillus subtilis and Staphylococcus

aureus respectively as shown in figure-4 but do not showed any

inhibitory action against Pseudomonas aeroginosa. The azo

compound 1d showed 13.6, 12.8, 15.6 and 14.4 mm zones of

inhibition against the test pathogens Escherichia coli,

Salmonella typhi, Pseudomonas aeroginosa and Staphylococcus

aureus as shown in figure-5. Compound 1d showed 11.3 mm

zone of inhibition against the pathogen Bacillus subtilis.

R

NH2

NaNO2 +HCl

0-5oC

N=N Cl

1

C2H5O

2R

C2H5O

5-10 oC

N=N Ar

1a-d

OH

CHO

OH

CHO

Ar =

O2N

CH3

a b c d Figure-1

The general reaction scheme for synthesis of azo compounds of ethyl vanillin

Table-1

The symbols, compounds name, molecular formulae, molecular weights, melting points and percentage yield of synthesized

azo compounds of ethyl vanillin

Symbols for

antimicrobial

activity

Symbols

for

FTIR and

H1 NMR

Compounds

Name

Molecular

Formulae

Molecular

Weights

Melting

points

(0C)

Yield

(%)

1a 4P 3-ethoxy-4-hydroxy-5-

(phenyldiazenyl)benzaldehyde C15H14N2O3 270.28 67 67

1b 4Q 3-ethoxy-4-hydroxy-5-((2-

nitrophenyl)diazenyl)benzaldehyde C15H13N3O5 315.28 128-130 65

1c 4R 3-ethoxy-4-hydroxy-5-(p-

tolyldiazenyl)benzaldehyde C16H16N2O3 284.31 64 72

1d 4S 3-ethoxy-4-hydroxy-5-(napthalen-1-

yldiazenyl)benzaldehyde C19H16N2O3 320.34 127-129 80

Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X

Vol. 5(7), 20-28, July (2015) Res. J. Chem. Sci.

International Science Congress Association 22

Table-2

FTIR and H1 NMR data of synthesized azo compounds of ethyl vanillin

Symbols for

compounds Types of spectra FTIR and H

1 NMR spectral data

4P

FTIR (KBr,cm-1

) 3362 (OH of Phenol), 2829 (C-H of H-C=O), 1686 (C=O), 1516 (C=C), 1255 (C-O),

1280 (C-N), 1579 (N=N).

H1 NMR (δ ppm)

1.4 (t, 3H of -CH3), 4.2 (q, 2H of -OCH2), 6.2 (s, 1H of Phenolic -OH), 9.8 (s, 1H of -

CHO), 7.0 to 7.5 (m, 7H of Aromatic-H).

4Q

FTIR (KBr,cm-1

) 3398 (OH of Phenol), 2882 (C-H of H-C=O), 1673 (C=O), 1519 (C=C), 1262 (C-O),

1232 (C-N), 1590 (N=N).

H1 NMR (δ ppm)

1.5 (t, 3H of -CH3), 4.4 (q, 2H of -OCH2), 4.2 (s, 1H of Phenolic -OH), 9.8 (s, 1H of -

CHO), 7.0 to 8.5 (m, 6H of Aromatic-H), 9.9 due to moisture.

4R

FTIR (KBr,cm-1

) 3363 (OH of Phenol), 2828 (C-H of H-C=O), 1681 (C=O), 1514 (C=C), 1281 (C-O),

1168 (C-N), 1580 (N=N).

H1 NMR (δ ppm)

1.5 (t, 3H of -CH3), 4.3 (q, 2H of -OCH2), 6.3 (s, 1H of Phenolic -OH), 9.8 (s, 1H of -

CHO), 7.0 to 7.4 (m, 6H of Aromatic-H).

4S

FTIR (KBr,cm-1

) 3333 (OH of Phenol), 2842 (C-H of H-C=O), 1682 (C=O), 1515 (C=C), 1261 (C-O),

1231 (C-N), 1592 (N=N).

H1 NMR (δ ppm)

1.5 (t, 3H of -CH3), 4.1 (q, 2H of -OCH2), 4.3 (s, 1H of Phenolic -OH), 9.8 (s, 1H of -

CHO), 7.0 to 8.5 (m, 9H of Aromatic-H).

Table-3

Antimicrobial activities of the synthesized azo compounds of ethyl vanillin

Symbols for

compounds

Microbial species and diameter of zone of inhibition in mm

Escherichia coli Salmonella typhi Pseudomonas

aeroginosa Bacillus subtilis

Staphylococcus

aureus

1a 10.4 No inhibition No inhibition No inhibition 9.6

1b 10.6 12.7 No inhibition 11.8 9.8

1c 10.3 13.1 No inhibition 13.5 12.8

1d 13.6 12.8 15.6 11.3 14.4

E. coli S. aureus

Figure-2

Zone of inhibition of azo compound 1a

E. coli S. typhi B. subtilis S. aureus

Figure-3

Zone of inhibition of azo compound 1b

Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X

Vol. 5(7), 20-28, July (2015) Res. J. Chem. Sci.

International Science Congress Association 23

E. coli S. typhi B. subtilis S.aureus

Figure-4

Zone of inhibition of azo compound 1c

E. coli S. typhi P. aeroginosa S.aureus

Figure-5

Zone of inhibition of azo compound 1d

Pagariya-21.sp - 4/21/2014 - 4P

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400.0

0.0

5

10

15

20

25

30

35

40

45

50

55.4

cm-1

%T

3729,53

3362,13

2979,302934,29

2887,34

2829,29

2797,322722,35

2681,402539,42

2331,45

2097,49 1908,49

1782,52

1686,71674,8

1604,18

1579,51516,7

1477,29

1439,17

1398,261380,27

1280,4

1255,9

1197,14

1168,4

1115,101104,10

1041,15

970,23

890,37

852,27

839,20

802,27

786,21

734,40

653,27633,25

585,28524,26

416,47

Figure-6

FTIR spectrum of azo compound 1a

Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X

Vol. 5(7), 20-28, July (2015) Res. J. Chem. Sci.

International Science Congress Association 24

Pagariya-22.sp - 4/21/2014 - 4Q

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400.0

31.5

35

40

45

50

55

60

65.4

cm-1

%T

3398,57

2982,56

2926,582882,59

2843,58

2757,60

1673,37

1590,41

1519,38

1441,41

1335,48

1308,41

1262,34

1232,42

1126,43

1041,48

878,45851,45

829,45742,42

639,45

590,51

530,54

Figure-7

FTIR spectrum of azo compound 1b

S K Pagariya-1.sp - 5/12/2015 - 4R

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400.0

7.0

8

10

12

14

16

18

20

22

24

26

28

30

32

33.5

cm-1

%T

3778,31

3363,17

2980,202934,19

2887,20

2828,192796,20

2724,20

2540,23

2321,24

2096,27

1907,28

1681,111580,11

1514,11

1439,14

1396,171382,17

1281,101257,11

1168,10

1107,12

1040,13

969,16

889,21

837,16

801,18

783,16633,16

584,18522,19

415,30

Figure-8

FTIR spectrum of azo compound 1c

Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X

Vol. 5(7), 20-28, July (2015) Res. J. Chem. Sci.

International Science Congress Association 25

S K Pagariya-2.sp - 5/12/2015 - 4S

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400.0

2.0

4

6

8

10

12

14

16

18

18.7

cm-1

%T

3333,14

3054,12

2981,10

2927,112882,12

2842,11

2758,13

2351,16

2007,181938,18

1871,17

1682,4

1592,51515,6

1487,6

1442,51401,6

1308,51283,5

1261,4

1231,5

1165,7

1136,5

1041,81003,8

878,6860,6

828,6795,6

767,5

741,6716,5

638,6

590,8574,8

545,9

489,11

424,14

Figure-9

FTIR spectrum of azo compound 1d

13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm

0.0000

1.4622

1.4797

1.4971

4.1735

4.1910

4.2085

4.2260

6.3361

7.0335

7.0538

7.2680

7.4013

7.4200

7.4245

9.8170

3.35

2.20

1.04

1.01

2.06

1.00

Current Data ParametersNAME May13-2014-AdministratorEXPNO 50PROCNO 1

F2 - Acquisition ParametersDate_ 20140513Time 17.32INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 287DW 41.600 usecDE 6.00 usecTE 296.7 KD1 1.00000000 secTD0 1

======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz

F2 - Processing parametersSI 32768SF 400.1300064 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00

4PBRUKERAVANCE II 400 NMRSpectrometer

SAIFPanjab UniversityChandigarh

[email protected] Figure-10

H1 NMR spectrum of azo compound 1a

Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X

Vol. 5(7), 20-28, July (2015) Res. J. Chem. Sci.

International Science Congress Association 26

15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm

1.2431

1.2542

1.4019

1.4666

1.4743

1.4841

1.4916

1.5016

1.5091

1.5321

1.6176

1.6380

4.0919

4.1092

4.1662

4.1787

4.1831

4.1963

4.2137

4.2310

7.0325

7.0520

7.2635

7.3995

7.4190

7.4232

7.4318

7.4470

7.4673

7.5105

7.5176

7.5474

7.5574

7.5760

7.6299

7.6450

7.6590

7.6634

7.6724

7.6995

7.7180

7.7311

7.7855

8.0220

8.0542

8.0701

8.1306

8.1637

9.8171

9.9354

13.7555

14.5427

2.21

6.97

2.16

1.04

3.57

0.68

1.00

3.45

5.47

4.50

0.56

1.05

0.38

0.36

Current Data ParametersNAME May13-2014-AdministratorEXPNO 60PROCNO 1

F2 - Acquisition ParametersDate_ 20140513Time 17.37INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 912DW 41.600 usecDE 6.00 usecTE 296.7 KD1 1.00000000 secTD0 1

======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz

F2 - Processing parametersSI 32768SF 400.1300083 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00

4QBRUKERAVANCE II 400 NMR

SpectrometerSAIFPanjab UniversityChandigarh

[email protected] Figure-11

H1 NMR spectrum of azo compound 1b

13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm

0.0000

1.4595

1.4770

1.4945

4.1702

4.1877

4.2052

4.2226

6.3759

7.0331

7.0528

7.2702

7.4008

7.4196

7.4239

9.8151

3.31

2.15

1.00

1.07

2.03

1.01

Current Data ParametersNAME May13-2014-AdministratorEXPNO 70PROCNO 1

F2 - Acquisition ParametersDate_ 20140513Time 17.42INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 512DW 41.600 usecDE 6.00 usecTE 296.8 KD1 1.00000000 secTD0 1

======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz

F2 - Processing parametersSI 32768SF 400.1300055 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00

4RBRUKERAVANCE II 400 NMRSpectrometerSAIFPanjab UniversityChandigarh

[email protected] Figure-12

H1 NMR spectrum of azo compound 1c

Research Journal of Chemical Sciences ___________________________________________________________ ISSN 2231-606X

Vol. 5(7), 20-28, July (2015) Res. J. Chem. Sci.

International Science Congress Association 27

15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm

1.5105

1.5283

1.5551

1.5725

1.5899

1.6178

1.6350

1.6524

4.1694

4.1869

4.2044

4.2239

4.2417

4.2592

4.2766

4.2870

4.3362

4.3539

7.0285

7.0480

7.2588

7.3936

7.4127

7.4987

7.5020

7.5276

7.5420

7.5508

7.5764

7.6001

7.6197

7.6355

7.6403

7.6640

7.6810

7.7272

7.7743

7.7797

7.8555

7.9336

7.9517

7.9716

7.9963

8.0301

8.0430

8.0498

8.0617

8.1352

8.1390

8.4134

8.4831

8.5038

8.5623

9.8137

9.9637

14.8291

1.30

4.64

2.94

0.49

0.70

0.81

1.55

4.88

1.99

2.32

1.17

1.00

0.98

1.01

Current Data ParametersNAME May13-2014-AdministratorEXPNO 80PROCNO 1

F2 - Acquisition ParametersDate_ 20140513Time 17.49INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 812DW 41.600 usecDE 6.00 usecTE 297.0 KD1 1.00000000 secTD0 1

======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz

F2 - Processing parametersSI 32768SF 400.1300103 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00

4SBRUKERAVANCE II 400 NMRSpectrometer

SAIFPanjab UniversityChandigarh

[email protected] Figure-13

H1 NMR spectrum of azo compound 1d

Conclusion

The current investigation reveals that, there was a miraculous

inhibition of compound 1d shows antibacterial activity against

all the tested organisms while the compound 1a was found to be

most resistant by the pathogens. The highest zone of inhibition

was obtained for 1d against Pseudomonas aeroginosa (15.6

mm) while lowest zone was recorded for 1a against

Staphylococcus aureus (9.6 mm). The compounds 1b and 1c

shows moderate inhibition of growth against tested pathogens.

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