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CHAPTER 3 RESULTS AND DISCUSSION Twelve amphiphilic Schiff bases were synthesized as mentioned in chapter 2. Figures 3.1(a) (b) (c), 3.2 (a) (b) (c), 3.3 (a) (b) (c) and 3.4 (a) (b) (c) show the molecular models of the synthesized compounds 1A, 2A, 3A, 1B, 2B, 3B, 1C, 2C, 3C, 1D, 2D and 3D (geometrically optimized) with their molecular weights.
1A
a)
Molecular Weight: 374 2A
b)
Molecular Weight: 479 c)
3A
Molecular Weight: 402 Figure 3.1 Molecular models of compounds a) 1A, b) 2A and c) 3A
a) 1B
Molecular Weight: 372
b) 2B
Molecular Weight: 477
c) 3B
Molecular Weight: 400
Figure 3.2 Molecular models of compounds a) 1B, b) 2B and 3B
a)
1C
Molecular Weight: 354
b)
2C
Molecular Weight: 459 3C c)
Molecular Weight: 382 Figure 3.3 Molecular models of compounds a) 1C, b) 2C and c) 3C
a)
1D
Molecular Weight: 347
b) 2D
Molecular Weight: 452
c)
3D
Molecular Weight: 375
Figure 3.4 Molecular models of compounds a) 1D, b) 2D and c) 3D
Compounds synthesized were characterized using techniques mentioned in chapter 2.
3.1 Mass spectra Using mass spectroscopy, the molecular weights of the compounds were estimated. Figures 3.5, 3.6, 3.7, 3.8, 3.9, 3.10 and 3.11 give the mass spectra of the samples.
Figure 3.5 Mass spectra of 1A
a)
b)
Figure 3.6 Mass spectra of a) 2A and b) 3A
a)
b)
Figure 3.7 Mass spectra of a) 1B and b) 2B
a)
b)
Figure 3.8 Mass spectra of a) 3B and b) 1C
a)
b)
Figure 3.9 Mass spectra of a) 2C and b) 3C
a)
b)
Figure 3.10 Mass spectra of a) 1D and b) 2D
Figure 3.11 Mass spectra of 3D
3.2 FT-IR spectra The functional groups present in the compounds were determined from the FT-IR spectra. The peak assignments of the FT-IR spectra are given in tables 3.1, 3.2, 3.3 and 3.4. The spectra are shown in figures 3.12, 3.13, 3.14 and 3.15. In all spectra a peak between 1600-1650cm-1 confirms the presence of -CH=N group and hence the
StC=N 1604.6 1613.8 1603.6
Table 3.1. Peak FTIR spectra of
P e rc e n ta g e
Sample 1A 2A 3A
T r a n s m itt a n c e
formation of Schiff’s base. St NO2(sym) 8 0 1342.6 7 0 1347.2 6 0 1341.2
StNO2(asym) 1528.9 1516.9 1528.8
StN-H -----3410.9 ------
StCH2(sym) 1 A 2848.3 2848.5 2847.6
StCH2(asym) 2922.1 2921.4 2921.3
BCH3&BCH2 1463.2 1468.9 1463.8
5 0 4 0
1 6 0 4 .6
3 0
1 4 6 3 .2
2 0 1 0 0
assignments for 1A, 2A and 3A
8 5 6 .6
2 8 4 8 .3 2 9 2 2 .1
1 5 2 8 . 91 3 4 2 . 6
4 0 0 0 3 5 0 0 3 0 0 0 2 5 0 0 2 0 0 0 1 5 0 0 1 0 0 0 5 0 0
W a v e n u m b e r (c m -1 )
a)
b)
c)
Percentage transmittance
3A 80 70 60 50 40
1603.6
845.7
30
1463.8
20
2847.6 2921.3
10 0 4000
3500
3000
2500
1528
2000
1341.2
1500
1000
500
Wavenumber (cm-1)
Figure 3.12 FT-IR spectra of a) 1A, b) 2A and c) 3A
Sample
StC=N
StalkylCN
StarylCN
StN-H
StCH2(sym)
StCH2(asym)
BCH3&BCH2
1B 2B 3B
1616.3 1606.8 1615.9
1230.5 1267.7 1230.2
1372.9 1370.8 1371.4
-----3277.9 ------
2849.4 2849.6 2849.3
2918.5 2917.7 2918.4
1464.9 1471.1 1467.1
P e rc e n ta g e
a)
T r a n s m it ta n c e
Table 3.2. Peak assignments for FTIR spectra of 1B, 2B and 3B
8 0
1 B
7 0 6 0 5 0
5 9 4 .3
4 0
7 2 3 .4 1 2 3 0 .5 1 4 6 4 .9 1 3 7 2 .9
3 0 2 0 1 0 0
2 8 4 9 .4 1 6 1 6 .3 2 9 1 8 .5
4 0 0 0 3 5 0 0 3 0 0 0 2 5 0 0 2 0 0 0 1 5 0 0 1 0 0 0 5 0 0
W a v e n u m b e r (c m -1 )
b)
Figure 3.13 FT-IR spectra of a) 1B, b) 2B
t r a n s m it ta n c e P e rc e n ta g e
c)
8 0
3 B
7 0 6 0 5 0 4 0 3 0 2 0 1 0
7 9 4 .2 1 2 3 0 .2 1 4 6 7 .1 2 8 4 9 .3 1 3 7 1 .4 1 6 1 5 .9 2 9 1 8 .4
0 4 0 0 0 3 5 0 0 3 0 0 0 2 5 0 0 2 0 0 0 1 5 0 0 1 0 0 0 5 0 0
W a v e n u m b e r (c m -1 )
Figure 3.13 c) FT-IR spectra of 3B
Sample 1C 2C 3C
StC=N 1650.2 1613.7 1649.0
StC≡N 2225.9 2229.3 2225.2
StN-H -----3319.5 ------
StCH2(sym) 2849.7 2851.6 2848.9
StCH2(asym) 2917.4 2918.2 2917.3
a)
P e r c e n ta g e T r a n s m it t a n c e
Table 3.3 Peak assignments for FTIR spectra of 1C, 2C and 3C
100
1 C 80
60
2 2 2 5 .9
5 5 3 .9
1 6 5 0 .2
40
8 3 5 .0
1 4 7 0 .9 20
2 8 4 9 .7 2 9 1 7 .4
0 400035003000 25002 00015001000 500
W a v e n u m b e r (c m -1 )
Figure 3.14 a) FT-IR spectra of 1C,
BCH3&BCH2 1470.9 1470.9 1469.9
b)
c)
Percentage transmittance
100
3C
80
60
2225.2
554.3
1649.0
40
845.7 1469.9
20
2848.9 2917.3
0 4000
3500
3000
2500
2000
1500
1000
500
Wavenumber (cm-1)
Figure 3.14 FT-IR spectra of b) 2C and c) 3C
StC=N 1644.1 1602.4 1644.1
Table3.4 Peak spectra of 1D, 2D a)
Percentage transmittance
Sample 1D 2D 3D
60 50
StC-F 1225.3 1225.3 1222.8
StN-H -----3373.1 ------
StCH2(sym) 2851.4 1D 2849.9 2849.9
40
BCH3&BCH2 1465.3 1466.4 1470.2
assignments for FTIR and 3D
30 20
715.9 843.2
1644.1
10 0 4000
StCH2(asym) 2912.6 2912.6 2912.6
2851.4
1225.3 1465.3
2912.6 3500
3000
2500
2000
1500
Wavenumber (cm-1)
1000
500
b)
100
2D
Percentage transmittance
80
512.6
60
40
828.4
3373.1
1602.4 1225.3 1466.4
20
0 4000
2848.9 2912.6 3500
3000
2500
2000
1500
1000
500
Wavenumber (cm-1)
c) 80
3D
Percentage transmittance
70 60 50
718.4
40
1470
20
1222.8
2848.9
10 0 4000
840.8
1644.1
30
2912.6 3500
3000
2500
2000
1500
1000
500
Wavenumber (cm-1)
Figure 3.15 FT-IR spectra of a) 1D, b) 2D and c) 3D 3.3 NMR spectra
The carbon skeletons of the compounds were determined from NMR spectra. Figures 3.16, 3.17, 3.18, 3.19, 3.20, 3.21, 3.22, 3.23, 3.24, 3.25, 3.26 and 3.27 represents 1H NMR spectra of the samples 1A, 2A, 3A, 1B, 2B, 3B, 1C, 2C, 3C, 1D, 2D, 3D respectively. The interpretations of the spectra are tabulated in table 3.5
Sample
-CH3 (t)
-CH2-CH3 (m)
-(CH2)n(m)
=N-CH2 (t)
-CH=N (s)
Ph-H (d)
-Ph-NH (s)
=N-CH2Ph (s)
1A
0.87
1.71
1.24
3.66
8.34
----
----
2A
0.87
1.60
1.25
3.09
8.39
7.25
4.76
3A
0.87
1.71
1.24
3.66
8.34
----
----
1B
0.87
1.66
1.24
3.53
8.12
----
----
2B
0.87
1.59
1.25
3.08
8.19
7.25
4.65
3B
0.87
1.66
1.24
3.53
8.12
----
----
1C
0.87
1.69
1.24
3.64
8.28
----
----
2C
0.87
1.60
1.24
3.08
8.34
7.25
4.74
3C
0.87
1.69
1.24
3.63
8.28
----
----
1D
0.87
1.67
1.24
3.57
8.22
----
----
2D
0.87
1.60
1.25
3.08
8.29
7.12
4.69
3D
0.87
1.67
1.24
3.58
8.22
7.88, 8.25 6.59, 7.11, 7.90, 8.24 7.88, 8.25 6.68, 7.59 6.57, 6.68, 7.11, 7.64 6.68, 7.59 7.68, 7.81 6.58, 7.10, 7.67, 7.84 7.68, 7.81 7.07, 7.69 6.57, 7.08, 7.73, 7.75 7.07, 7.70
----
----
Table 3.5 Interpretation of 1H NMR spectra
1A
Figure 3.16 1H NMR spectrum of 1A
2A
F
igu re 3.17 1H NMR spectrum of 2A
Figure 3.18 1H NMR spectrum of 3A
Figure 3.19 1H NMR spectrum of 1B
Figure 3.20 1H NMR spectrum of 2B
Figure 3.21 1H NMR spectrum of 3B
F
igu
re
3.22 1H NMR spectrum of 1C
Figure 3.23 1H NMR spectrum of 2C
3C
Figure 3.24 1H NMR spectrum of 3C
1D
Figure 3.25 1H NMR spectrum of 1D
F re
igu 2D
3.26 1H NMR spectrum of 2D
Figure 3.27 1H NMR spectrum of 3D
1A
a)
Molecular Weight: 374 2A
b)
Molecular Weight: 479 c)
3A
Molecular Weight: 402 Figure 3.1 Molecular models of compounds a) 1A, b) 2A and c) 3A
a) 1B
Molecular Weight: 372
b) 2B
Molecular Weight: 477
c) 3B
Molecular Weight: 400
Figure 3.2 Molecular models of compounds a) 1B, b) 2B and 3B
a)
1C
Molecular Weight: 354
b)
2C
Molecular Weight: 459 3C c)
Molecular Weight: 382 Figure 3.3 Molecular models of compounds a) 1C, b) 2C and c) 3C
a)
1D
Molecular Weight: 347
b) 2D
Molecular Weight: 452
c)
3D
Molecular Weight: 375
Figure 3.4 Molecular models of compounds a) 1D, b) 2D and c) 3D
Compounds synthesized were characterized using techniques mentioned in chapter 2.
3.1 Mass spectra Using mass spectroscopy, the molecular weights of the compounds were estimated. Figures 3.5, 3.6, 3.7, 3.8, 3.9, 3.10 and 3.11 give the mass spectra of the samples.
Figure 3.5 Mass spectra of 1A
a)
b)
Figure 3.6 Mass spectra of a) 2A and b) 3A
a)
b)
Figure 3.7 Mass spectra of a) 1B and b) 2B
a)
b)
Figure 3.8 Mass spectra of a) 3B and b) 1C
a)
b)
Figure 3.9 Mass spectra of a) 2C and b) 3C
a)
b)
Figure 3.10 Mass spectra of a) 1D and b) 2D
Figure 3.11 Mass spectra of 3D
3.2 FT-IR spectra The functional groups present in the compounds were determined from the FT-IR spectra. The peak assignments of the FT-IR spectra are given in tables 3.1, 3.2, 3.3 and 3.4. The spectra are shown in figures 3.12, 3.13, 3.14 and 3.15. In all spectra a peak between 1600-1650cm-1 confirms the presence of -CH=N group and hence the
StC=N 1604.6 1613.8 1603.6
Table 3.1. Peak FTIR spectra of
P e rc e n ta g e
Sample 1A 2A 3A
T r a n s m itt a n c e
formation of Schiff’s base. St NO2(sym) 8 0 1342.6 7 0 1347.2 6 0 1341.2
StNO2(asym) 1528.9 1516.9 1528.8
StN-H -----3410.9 ------
StCH2(sym) 1 A 2848.3 2848.5 2847.6
StCH2(asym) 2922.1 2921.4 2921.3
BCH3&BCH2 1463.2 1468.9 1463.8
5 0 4 0
1 6 0 4 .6
3 0
1 4 6 3 .2
2 0 1 0 0
assignments for 1A, 2A and 3A
8 5 6 .6
2 8 4 8 .3 2 9 2 2 .1
1 5 2 8 . 91 3 4 2 . 6
4 0 0 0 3 5 0 0 3 0 0 0 2 5 0 0 2 0 0 0 1 5 0 0 1 0 0 0 5 0 0
W a v e n u m b e r (c m -1 )
a)
b)
c)
Percentage transmittance
3A 80 70 60 50 40
1603.6
845.7
30
1463.8
20
2847.6 2921.3
10 0 4000
3500
3000
2500
1528
2000
1341.2
1500
1000
500
Wavenumber (cm-1)
Figure 3.12 FT-IR spectra of a) 1A, b) 2A and c) 3A
Sample
StC=N
StalkylCN
StarylCN
StN-H
StCH2(sym)
StCH2(asym)
BCH3&BCH2
1B 2B 3B
1616.3 1606.8 1615.9
1230.5 1267.7 1230.2
1372.9 1370.8 1371.4
-----3277.9 ------
2849.4 2849.6 2849.3
2918.5 2917.7 2918.4
1464.9 1471.1 1467.1
P e rc e n ta g e
a)
T r a n s m it ta n c e
Table 3.2. Peak assignments for FTIR spectra of 1B, 2B and 3B
8 0
1 B
7 0 6 0 5 0
5 9 4 .3
4 0
7 2 3 .4 1 2 3 0 .5 1 4 6 4 .9 1 3 7 2 .9
3 0 2 0 1 0 0
2 8 4 9 .4 1 6 1 6 .3 2 9 1 8 .5
4 0 0 0 3 5 0 0 3 0 0 0 2 5 0 0 2 0 0 0 1 5 0 0 1 0 0 0 5 0 0
W a v e n u m b e r (c m -1 )
b)
Figure 3.13 FT-IR spectra of a) 1B, b) 2B
t r a n s m it ta n c e P e rc e n ta g e
c)
8 0
3 B
7 0 6 0 5 0 4 0 3 0 2 0 1 0
7 9 4 .2 1 2 3 0 .2 1 4 6 7 .1 2 8 4 9 .3 1 3 7 1 .4 1 6 1 5 .9 2 9 1 8 .4
0 4 0 0 0 3 5 0 0 3 0 0 0 2 5 0 0 2 0 0 0 1 5 0 0 1 0 0 0 5 0 0
W a v e n u m b e r (c m -1 )
Figure 3.13 c) FT-IR spectra of 3B
Sample 1C 2C 3C
StC=N 1650.2 1613.7 1649.0
StC≡N 2225.9 2229.3 2225.2
StN-H -----3319.5 ------
StCH2(sym) 2849.7 2851.6 2848.9
StCH2(asym) 2917.4 2918.2 2917.3
a)
P e r c e n ta g e T r a n s m it t a n c e
Table 3.3 Peak assignments for FTIR spectra of 1C, 2C and 3C
100
1 C 80
60
2 2 2 5 .9
5 5 3 .9
1 6 5 0 .2
40
8 3 5 .0
1 4 7 0 .9 20
2 8 4 9 .7 2 9 1 7 .4
0 400035003000 25002 00015001000 500
W a v e n u m b e r (c m -1 )
Figure 3.14 a) FT-IR spectra of 1C,
BCH3&BCH2 1470.9 1470.9 1469.9
b)
c)
Percentage transmittance
100
3C
80
60
2225.2
554.3
1649.0
40
845.7 1469.9
20
2848.9 2917.3
0 4000
3500
3000
2500
2000
1500
1000
500
Wavenumber (cm-1)
Figure 3.14 FT-IR spectra of b) 2C and c) 3C
StC=N 1644.1 1602.4 1644.1
Table3.4 Peak spectra of 1D, 2D a)
Percentage transmittance
Sample 1D 2D 3D
60 50
StC-F 1225.3 1225.3 1222.8
StN-H -----3373.1 ------
StCH2(sym) 2851.4 1D 2849.9 2849.9
40
BCH3&BCH2 1465.3 1466.4 1470.2
assignments for FTIR and 3D
30 20
715.9 843.2
1644.1
10 0 4000
StCH2(asym) 2912.6 2912.6 2912.6
2851.4
1225.3 1465.3
2912.6 3500
3000
2500
2000
1500
Wavenumber (cm-1)
1000
500
b)
100
2D
Percentage transmittance
80
512.6
60
40
828.4
3373.1
1602.4 1225.3 1466.4
20
0 4000
2848.9 2912.6 3500
3000
2500
2000
1500
1000
500
Wavenumber (cm-1)
c) 80
3D
Percentage transmittance
70 60 50
718.4
40
1470
20
1222.8
2848.9
10 0 4000
840.8
1644.1
30
2912.6 3500
3000
2500
2000
1500
1000
500
Wavenumber (cm-1)
Figure 3.15 FT-IR spectra of a) 1D, b) 2D and c) 3D 3.3 NMR spectra
The carbon skeletons of the compounds were determined from NMR spectra. Figures 3.16, 3.17, 3.18, 3.19, 3.20, 3.21, 3.22, 3.23, 3.24, 3.25, 3.26 and 3.27 represents 1H NMR spectra of the samples 1A, 2A, 3A, 1B, 2B, 3B, 1C, 2C, 3C, 1D, 2D, 3D respectively. The interpretations of the spectra are tabulated in table 3.5
Sample
-CH3 (t)
-CH2-CH3 (m)
-(CH2)n(m)
=N-CH2 (t)
-CH=N (s)
Ph-H (d)
-Ph-NH (s)
=N-CH2Ph (s)
1A
0.87
1.71
1.24
3.66
8.34
----
----
2A
0.87
1.60
1.25
3.09
8.39
7.25
4.76
3A
0.87
1.71
1.24
3.66
8.34
----
----
1B
0.87
1.66
1.24
3.53
8.12
----
----
2B
0.87
1.59
1.25
3.08
8.19
7.25
4.65
3B
0.87
1.66
1.24
3.53
8.12
----
----
1C
0.87
1.69
1.24
3.64
8.28
----
----
2C
0.87
1.60
1.24
3.08
8.34
7.25
4.74
3C
0.87
1.69
1.24
3.63
8.28
----
----
1D
0.87
1.67
1.24
3.57
8.22
----
----
2D
0.87
1.60
1.25
3.08
8.29
7.12
4.69
3D
0.87
1.67
1.24
3.58
8.22
7.88, 8.25 6.59, 7.11, 7.90, 8.24 7.88, 8.25 6.68, 7.59 6.57, 6.68, 7.11, 7.64 6.68, 7.59 7.68, 7.81 6.58, 7.10, 7.67, 7.84 7.68, 7.81 7.07, 7.69 6.57, 7.08, 7.73, 7.75 7.07, 7.70
----
----
Table 3.5 Interpretation of 1H NMR spectra
1A
Figure 3.16 1H NMR spectrum of 1A
2A
F
igu re 3.17 1H NMR spectrum of 2A
Figure 3.18 1H NMR spectrum of 3A
Figure 3.19 1H NMR spectrum of 1B
Figure 3.20 1H NMR spectrum of 2B
Figure 3.21 1H NMR spectrum of 3B
F
igu
re
3.22 1H NMR spectrum of 1C
Figure 3.23 1H NMR spectrum of 2C
3C
Figure 3.24 1H NMR spectrum of 3C
1D
Figure 3.25 1H NMR spectrum of 1D
F re
igu 2D
3.26 1H NMR spectrum of 2D
Figure 3.27 1H NMR spectrum of 3D
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