Chapter 3 (1) Doc

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.
a) 1A
Molecular Weight: 374
2A
b)
c)
3A
Figure 3.1 Molecular models of compounds a) 1A, b) 2A and c) 3A

a)
1B
b)
2B
c)
3B
Figure 3.2 Molecular models of compounds a) 1B, b) 2B and 3B

a)
1C
b)
2C
3C
c)
Figure 3.3 Molecular models of compounds a) 1C, b) 2C and c) 3C

a)
1D
b)
2D
c)
3D
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
formation of Schiff’s base.

T r a n s m itt a n c e
Sample StC=N St NO2(sym)

8 0
StNO2(asym) StN-H StCH2(sym) StCH2(asym) BCH3&BCH2
1 A
1A 1604.6 1342.6 1528.9 ------ 2848.3 2922.1 1463.2
7 0
2A 1613.8 1347.2 1516.9 3410.9 2848.5 2921.4 1468.9
6 0
3A 1603.6 1341.2 1528.8 ------ 2847.6 2921.3 1463.8
5 0
Table 3.1. Peak 4 0 assignments for

1 6 0 4 .6 8 5 6 .6
FTIR spectra of 1A, 2A and 3A
P e rc e n ta g e
3 0
2 0 1 4 6 3 .2
1 0 1 5 2 8 . 91 3 4 2 . 6
2 8 4 8 .3
0 2 9 2 2 .1
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)
3A
80
Percentage transmittance
70
c)
60
50
40 1603.6 845.7
30
1463.8
20
1528 1341.2
10
2847.6
2921.3
0
4000 3500 3000 2500 2000 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 1616.3 1230.5 1372.9 ------ 2849.4 2918.5 1464.9
2B 1606.8 1267.7 1370.8 3277.9 2849.6 2917.7 1471.1
3B 1615.9 1230.2 1371.4 ------ 2849.3 2918.4 1467.1
Table 3.2. Peak assignments for FTIR spectra of 1B, 2B and 3B

T r a n s m it ta n c e
a)
8 0
1 B
7 0
6 0
5 0 5 9 4 .3
4 0
7 2 3 .4
P e rc e n ta g e
3 0 1 2 3 0 .5
1 4 6 4 .9
2 0
1 3 7 2 .9
1 0 2 8 4 9 .4 1 6 1 6 .3
0 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
b)
Figure 3.13 FT-IR spectra of a) 1B, b) 2B

t r a n s m it ta n c e
8 0
3 B
c) 7 0
6 0
5 0
4 0
P e rc e n ta g e
7 9 4 .2
3 0
1 2 3 0 .2
2 0 2 8 4 9 .3 1 4 6 7 .1
1 3 7 1 .4
1 0 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
Figure 3.13 c) FT-IR spectra of 3B
Sample StC=N StC≡N StN-H StCH2(sym) StCH2(asym) BCH3&BCH2

1C 1650.2 2225.9 ------ 2849.7 2917.4 1470.9
2C 1613.7 2229.3 3319.5 2851.6 2918.2 1470.9
3C 1649.0 2225.2 ------ 2848.9 2917.3 1469.9
Table 3.3 Peak assignments for FTIR spectra of 1C, 2C and 3C

P e r c e n ta g e T r a n s m it t a n c e
a)
100
1 C
80
60
2 2 2 5 .9
5 5 3 .9
40 1 6 5 0 .2 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
Figure 3.14 a) FT-IR spectra of 1C,

b)
100
c) 80
3C
60
2225.2 554.3
40 1649.0 845.7
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
Sample StC=N StC-F StN-H StCH2(sym) StCH2(asym) BCH3&BCH2

1D 1644.1 60 1225.3 ------ 2851.4 2912.6 1465.3
1D
2D 1602.4 1225.3 3373.1 2849.9 2912.6 1466.4
50
3D 1644.1 1222.8 ------ 2849.9 2912.6 1470.2
40
Table3.4 Peak assignments for FTIR
spectra of 1D, 2D and 3D
30
715.9
20
a) 1644.1 843.2
1225.3
10
2851.4 1465.3
2912.6
0
4000 3500 3000 2500 2000 1500 1000 500
Wavenumber (cm-1)
b) 100
2D
80
60 512.6
40 828.4
3373.1
1602.4 1225.3
1466.4
20
2848.9
2912.6
0
4000 3500 3000 2500 2000 1500 1000 500
Wavenumber (cm-1)
c)
80
70 3D
60
50
718.4
40
1644.1 840.8
30
1470 1222.8
20
2848.9
10
2912.6
0
4000 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 -CH2-CH3 -(CH2)n- =N-CH2 -CH=N Ph-H -Ph-NH =N-CH2Ph
(t) (m) (m) (t) (s) (d) (s) (s)
1A 0.87 1.71 1.24 3.66 8.34 7.88, ---- ----

8.25
2A 0.87 1.60 1.25 3.09 8.39 6.59, 7.25 4.76
7.11,
7.90,
8.24
3A 0.87 1.71 1.24 3.66 8.34 7.88, ---- ----
8.25
1B 0.87 1.66 1.24 3.53 8.12 6.68, ---- ----
7.59
2B 0.87 1.59 1.25 3.08 8.19 6.57, 7.25 4.65
6.68,
7.11,
7.64
3B 0.87 1.66 1.24 3.53 8.12 6.68, ---- ----
7.59
1C 0.87 1.69 1.24 3.64 8.28 7.68, ---- ----
7.81
2C 0.87 1.60 1.24 3.08 8.34 6.58, 7.25 4.74
7.10,
7.67,
7.84
3C 0.87 1.69 1.24 3.63 8.28 7.68, ---- ----
7.81
1D 0.87 1.67 1.24 3.57 8.22 7.07, ---- ----
7.69
2D 0.87 1.60 1.25 3.08 8.29 6.57, 7.12 4.69
7.08,
7.73,
7.75
3D 0.87 1.67 1.24 3.58 8.22 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
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 igu
re
2D
3.26 1H NMR spectrum of 2D

Figure 3.27 1H NMR spectrum of 3D

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CHAPTER 3

RESULTS AND DISCUSSION

3D (geometrically optimized) with their molecular weights.

Molecular Weight: 374

Molecular Weight: 479

Molecular Weight: 402

Figure 3.1 Molecular models of compounds a) 1A, b) 2A and c) 3A

Molecular Weight: 372

Molecular Weight: 477

Molecular Weight: 400

Figure 3.2 Molecular models of compounds a) 1B, b) 2B and 3B

Molecular Weight: 354

Molecular Weight: 459

Molecular Weight: 382

Figure 3.3 Molecular models of compounds a) 1C, b) 2C and c) 3C

Molecular Weight: 347

Molecular Weight: 452

Molecular Weight: 375

Figure 3.4 Molecular models of compounds a) 1D, b) 2D and c) 3D

3.1 Mass spectra

Using mass spectroscopy, the molecular weights of the compounds were

Figure 3.5 Mass spectra of 1A

Figure 3.6 Mass spectra of a) 2A and b) 3A

Figure 3.7 Mass spectra of a) 1B and b) 2B

Figure 3.8 Mass spectra of a) 3B and b) 1C

Figure 3.9 Mass spectra of a) 2C and b) 3C

Figure 3.10 Mass spectra of a) 1D and b) 2D

3.2 FT-IR spectra

formation of Schiff’s base.

Sample StC=N St NO2(sym)

Table 3.1. Peak 4 0 assignments for

Figure 3.12 FT-IR spectra of a) 1A, b) 2A and c) 3A

Table 3.2. Peak assignments for FTIR spectra of 1B, 2B and 3B

Figure 3.13 FT-IR spectra of a) 1B, b) 2B

Figure 3.13 c) FT-IR spectra of 3B

Sample StC=N StC≡N StN-H StCH2(sym) StCH2(asym) BCH3&BCH2

Table 3.3 Peak assignments for FTIR spectra of 1C, 2C and 3C

Figure 3.14 a) FT-IR spectra of 1C,

Figure 3.14 FT-IR spectra of b) 2C and c) 3C

Sample StC=N StC-F StN-H StCH2(sym) StCH2(asym) BCH3&BCH2

Figure 3.15 FT-IR spectra of a) 1D, b) 2D and c) 3D

3.3 NMR spectra

respectively. The interpretations of the spectra are tabulated in table 3.5

1A 0.87 1.71 1.24 3.66 8.34 7.88, ---- ----

Table 3.5 Interpretation of 1H NMR spectra

Figure 3.16 1H NMR spectrum of 1A

re 3.17 1H NMR spectrum of 2A

3.22 1H NMR spectrum of 1C

Figure 3.24 1H NMR spectrum of 3C

Figure 3.25 1H NMR spectrum of 1D

3.26 1H NMR spectrum of 2D

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