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Title Antioxidant , Antibacterial and Spectroscopy study of new schiff base 2,2`-(1,2,5-oxadiazole-3,4-diyl) bis (azan-1- yl-1-ylidene) bis (methan -1-yl-1-ylidene) bis (4 -phenyldiazenyl)phenol. By:Zeinab Saki Overview Introduction

SLIDE 1

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Title

Antioxidant , Antibacterial and Spectroscopy study of new schiff base 2,2`-(1,2,5-oxadiazole-3,4-diyl) bis (azan-1- yl-1-ylidene) bis (methan -1-yl-1-ylidene) bis (4 -phenyldiazenyl)phenol.

By:Zeinab Saki

SLIDE 3

Overview

Introduction Structure Application Solvatochromism

Experimental

Antioxidant property Antibacterial property

SLIDE 4

Introduction

A Schiff base (or azomethine), named after Hogo Schiff, is functional group that contains a C=N with the nitrogen atom connected to an aryl

alkyl group.

Y.Hamada, l. Takeuchi, Y. Lta, S. Matsui and T. Ita, Yakugaku Zasslzi, 101, 633(1981): chem.Abstr., 95, 18155;1981

SLIDE 5

Structure R-N=N-R ' Azo : Schiff Base: R1R2C=N-R3 Azo Azomethine:

SLIDE 6

SLIDE 7

Y.Hamada, l. Takeuchi, Y. Lta, S. Matsui and T. Ita, Yakugaku Zasslzi, 101, 633(1981): chem.Abstr., 95, 18155;1981

SLIDE 8

SLIDE 9

)%( Randman ( C ° ) M.p Color Compound 55 123 Brown 1a 44 134 Dark brown 1b 50

130

Brown 1c 93.7 185 Yellow 1d 60 125 Brown 1e 45 128 Brown 1f

138 Orange 1g

N N R OH H O

Properties of Reactants

SLIDE 10

Synthesis of Schiff Base

MeOH

60-70 ℃ 8h

SLIDE 11

FT-IR spectrum

N N O H N N NON N N O H

N N O H H O

SLIDE 12

FT-IR spectrum

SLIDE 13

FT-IR

N-O Ar-O C-N C=C N=N C=N CH=N Ar-H OH compound 1037 1110 1284 1483 1573 1610 2910,2826 3068 3429 4a 1018 1163 1296 1485 1575 1600 2947,2857 3033 3442 4b 1033 1143 1280 1483 1581 1610 2918,2852 3058 3442 4c 1037 1149 1288 1481 1521 1635 2925,2854 3099 3417 4d 1045 1153 1280 1479 1521 1604 2958,2869 3039 3465 4e 1037 1153 1284 1481 1525 1606 2964,2871 3035 3460 4f 1033 1147 1278 1473 1583 1654 2939,2840 3035 3461 4g

SLIDE 14

1H NMR

D2O

N N OH N N N O N N N O H

SLIDE 15

N N OH N N N O N N N O H 1 2 3

13C NMR

SLIDE 16

1H NMR

D2O

SLIDE 17

13C NMR

N N N N O N N N N OH HO CH3 H3C

SLIDE 18

R Ar-H CH=N OH compound

8.19 – 7.17

10.35 11.57 4a 1.68 8.51 – 7.16 9.46 11.82 4b 2.28 8.02 – 7.09 9.40 11.81 4c

8.36 -7.22

10.58 11.89 4d

1H NMR

2.48 8.48-7.18 10.35 11.87 4e

SLIDE 19

Subs. Ar C3 C2 C1

number

151.86, 145.02, 131.128, 124.40, 124.36,

122.39, 120.80, 118.05, 110.91

156.48 162.81

167.02

4a 97.20

149.02, 145.10, 140.10, 140.62, 131.34, 128.69, 124.30, 122.30, 120.78, 118.00 156.46

162.58 167.00 4b 88.20

152.04, 145.17, 138.63, 132.54, 129.02, 124.32, 120.80, 120.30, 117.03 156.38

162.75 167.10 4c

152.12, 149.96,143.68, 129.78, 126.79,

124.08, 122.44, 122.08, 117.08

156.72 163.80 167.42 4d

13C NMR

23.64

151.78, 150.25, 144.88, 128.87, 127.22, 124.05, 122.47, 120.77,118.15

156.45 163.80 167.05 4e

SLIDE 20

Mass Spetroscopy

5 0 1 0 0 1 5 0 2 0 0 2 5 0 3 0 0 3 5 0 4 0 0 4 5 0 5 0 0 2 0 0 0 0 4 0 0 0 0 6 0 0 0 0 8 0 0 0 0 1 0 0 0 0 0 1 2 0 0 0 0 1 4 0 0 0 0 1 6 0 0 0 0 1 8 0 0 0 0 2 0 0 0 0 0 2 2 0 0 0 0 2 4 0 0 0 0 2 6 0 0 0 0 2 8 0 0 0 0 3 0 0 0 0 0 3 2 0 0 0 0 3 4 0 0 0 0 m / z - - > A b u n d a n c e S c a n 2 6 8 ( 2 . 4 5 2 m in ) : 6 4 0 0 7 3 9 0 . D 7 7 5 1 7 2 3 7 3 3 1 2 6 5 3 0 9 3 6 8 5 7 9 7 1 4 6 2 8 5 2 0 3 3 9 4 1 2 3 1 7 3 4 9 6 4 2 2 4 5 1 4 7 5

C28H20N8O3

m/Z=516

N N OH N N N O N N N O H

SLIDE 21

Solvatochromism

SLIDE 22

Effect of Substition

DMF

compound

416( A=0.634), 510(A=0.451)

398( A=0.634), 498( A= 0.357)

372( A=0.623), 490( A=0.350)

400( A=0.451), 508( A= 0.401)

389( A= 0.629). 485( A=0.334)

369( A=0.621), 482( A=0.332)

360( A= 0.619), 480( A=0.332)

a= NO2 b= H c= Me d= Et e= 3,5DiMe f= iso g= OMe

SLIDE 23

Effect of Solvent

compound

416( A=0.634), 510(A=0.451)

DMF

393( A= 0.386) ,477( A=0.252),

DMSO

382( A=0.481), 466( A=0.200)

THF

SLIDE 24

Effect of pH

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Effect of H2O

0.3 0.6 320 370 420 470 520 570 620 670 Absorbance(a.u) Wavelength

n m l

SLIDE 26

Hydrazone form

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Anti Microbial Properties Anti Oxidant Anti Bacterial

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Anti Oxidant

DPPH 1, 1-diphenyl-2- picryl-hydrazyl

SLIDE 29

DPPH

SLIDE 30

هنومن

SLIDE 31

Anti tioxidant xidant acti tivity vity

Number

C (mg/ml)

In(%) 4a

0.025

5.6 0.050

0.9

1.00 0.12 4b 0.025 0.050

0.5

1.00 0.32 4c 0.025 1.7 0.050 0.10 1.00 0.21 4d 0,025 0.050 6.4 1.00 17.4 4e 0.025 6.5 0.050 0.14 1.00 17.4 4f 0.025 8.0 0.050 26.0 1.00 34.5 4g 0.025 2.1 0.050 15.2 1.00 21.4 BHT 0.025 76.3 0.050 84.3 1.00 92.1

SLIDE 32

BHT> 4f > 4b > 4c > 4g > 4d > 4e > 4a Antioxidant Activity Curve

SLIDE 33

IC50 (mg/mL) compound

5.6

4a 1.4 4b 2.1 4c 2.4 4d 3.3 4e 1.3 4f 2.2 4g

IC50

SLIDE 34

Antibacterial

disc diffusion method

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لودج(3-7 :) تابیکرت یرتکاب دض تیلاعف( a-g 4 )کسید شور هب-راشتنا

S.Aureus B.Cereus

S.aureus B.cereus

C (μg/disc)

compound

11 10

12 13

13 8

10 8

13 12

11 12

9 9

21 25

Amikacin

DMSO

4f > 4e > 4b > 4c > 4a > 4d >4g

Growth Inhibition

SLIDE 37

Compare of Bacteries

5 10 15 20 1 2 3 4 5

Growth inhibition(mm) Compound

S.aureus B.cereus

SLIDE 38

SLIDE 39

Conclusion

1.It looks that, substitution of electron donor groups

n phenyl ring increases anti oxidant activity.
2. It looks that, substitution of non polar groups on

phenyl ring increases anti bacterial activities.