8 7 6 5 4 3 2 1 0 ppm
10.02
19.15
1.001.691.730.900.87
7.2 7.4
7.6
7.8 ppm
1.000
1.692
1.730
0.895
0.867
N N
S H
1
4 3 2
6
5
7 8
9
10
11
Figure 1: 1H NMR Spectrum of 2-(2-thienyl)-1H-benzimidazole (46a)
200 180 160 140 120 100 80 60 40 20 0 ppm
47.66
47.87
48.08
122.57
126.82
127.73
128.19
Figure 2: 13C NMR Spectrum of 2-(2-thienyl)-1H-benzimidazole (46a)
Figure 3: HRMS Spectrum of 2-(2-thienyl)-1H-benzimidazole (46a)
-1
9 8 7 6 5 4 3 2 1 0 ppm
0.90
0.871.681.002.00
6.8 7.0 7.2 7.4
7.6 ppm
0.897
0.871
1.675
1.000
2.000
N N H
O
1
1'
2 2'
4 3 5
6 7
3' 4'
5' 3a
7a
*
*
Figure 4: 1H NMR Spectrum of 2-(2-furanyl)-1H-benzimidazole (46b)*
* impurity
200 180 160 140 120 100 80 60 40 20 0 ppm
29.68
30.88
76.68
77.00
77.20
77.31
110.81
112.48
115.18
123.18
143.76
145.29
*
N N H
O
1
1' 2 2' 3
4 5
6 7
3' 4'
5' 3a
7a
Figure 5: 13C NMR Spectrum of 2-(2-furanyl)-1H-benzimidazole (46b)
200 180 160 140 120 100 80 60 40 20 0 ppm
30.88
110.81
112.48
115.14
123.18
143.76
*
N N H
O
1
1' 2 2' 3
4 5
6 7
3' 4'
5' 3a
7a
Figure 6: Dept 135 NMR Spectrum of 2-(2-furanyl)-1H-benzimidazole (46b)
Figure 7: HRMS Spectrum of 2-(2-furanyl)-1H-benzimidazole (46b)
10 9 8 7 6 5 4 3 2 1 0 ppm
2.10
1.01
1.76
1.08
1.00
1.00
7.2 7.4 7.6 7.8 8.0 8.2 8.4 8.6
8.8 ppm
2.103
1.014
1.765
1.085
1.000
0.996
N N
N H
Figure 8: 1H NMR Spectrum of 2-(2-Pyridyl)-1H-benzimidazole in CDCl3 (46c)
200 180 160 140 120 100 80 60 40 20 0 ppm
76.68
77.00
77.32
121.65
123.36
124.59
137.28
148.25
149.15
150.74
Figure 9: 13C NMR Spectrum of 2-(2-Pyridyl)-1H-benzimidazole in CDCl3 (46c)
110 115
120 125
130 135
140 145
150 155
160
165 ppm
121.65
123.37
124.58
137.28
149.15
Figure 10: Dept 135 Spectrum of 2-(2-Pyridyl)-1H-benzimidazole in CDCl3 (46c)
Figure 11: HRMS Spectrum of 2-(2-Pyridyl)-1H-benzimidazole (46c)
-1
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.12
1.001.011.03
0.982.240.992.011.02
7.0 7.2
7.4 7.6
7.8 ppm
1.000
1.011
1.030
0.982
2.236
0.988
2.007
1.023
N N
S S
1 2
3 4
5 6
7 8
9
10
11 12
13 14
15 16
Figure 12: 1H Spectrum of 1-(2-thienylmethyl)-2-(2-thienyl) benzimidazole in CDCl3 (49a)
60 70
80 90
100 110
120 130
140 150
160 170
180
190 ppm
44.11
76.69
77.01
77.22
77.33
109.93
119.95
123.03
123.35
125.42
125.52
127.23
127.90
128.15
128.92
131.80
135.89
138.82
142.96
147.58
Figure 13: 13C Spectrum of 1-(2-thienylmethyl)-2-(2-thienyl) benzimidazole in CDCl3 (49a)
50 60
70 80
90 100
110 120
130 140
150
160 ppm
44.11
109.93
119.95
123.03
123.35
125.42
125.51
127.23
127.90
128.15
128.92
Figure 14: Dept 135 Spectrum of 1-(2-thienylmethyl)-2-(2-thienyl) benzimidazole in CDCl3 (49a)
Figure 15: HRMS Spectrum of 1-(2-thienylmethyl)-2-(2-thienyl) benzimidazole (49a)
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.05
0.900.90
1.00
1.82
0.99
1.020.97
1.06
7.4 7.5
7.6 7.7
7.8 ppm
1.820
0.990
1.017
0.966
1.062
N N
O O
1 2
3 4
5 6
7 8
9
10
11 12
13
14 15 16
Figure 16: 1H Spectrum of 1-(2-furanylmethyl)-2-(2-furanyl) benzimidazole (49b)
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm
41.73
76.67
76.99
77.31
108.37
110.00
110.53
112.09
113.12
119.77
123.00
123.31
135.45
142.67
144.02
149.57
Figure 17: 13C Spectrum of 1-(2-furanylmethyl)-2-(2-furanyl) benzimidazole (49b)
200 180 160 140 120 100 80 60 40 20 ppm
41.73
108.37
110.00
110.53
112.09
119.77
123.00
123.31
142.67
144.02
Figure 18: Dept 135 Spectrum of 1-(2-furanylmethyl)-2-(2-furanyl) benzimidazole (49b)
Figure 19: HRMS Spectrum of 1-(2-furanylmethyl)-2-(2-furanyl) benzimidazole (49b)
14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
1.901.001.032.901.071.052.240.992.00
7.0 7.2 7.4 7.6 7.8 8.0 8.2 8.4
8.6 ppm
1.000
1.034
2.897
1.066
1.047
2.244
0.992
1.997
N
N N
N
Figure 20: 1H NMR Spectrum of 1-(2-Pyridylmethyl)-2-(2-pyridyl) benzimidazole in CDCl3 (49c)
200 180 160 140 120 100 80 60 40 20 0 ppm
51.12
76.68
77.00
77.32
110.83
120.08
120.98
122.27
123.03
123.77
123.89
124.65
136.80
136.85
136.88
142.55
148.65
149.17
149.81
150.30
157.43
Figure 21: 13C NMR Spectrum of 1-(2-Pyridylmethyl)-2-(2-pyridyl) benzimidazole in CDCl3 (49c)
50 60
70 80
90 100 110
120 130
140 150
160
170 ppm
51.12
110.83
120.08
120.98
122.27
123.03
123.77
123.89
124.65
136.85
136.88
148.65
149.17
Figure 22: Dept 135 Spectrum of 1-(2-Pyridylmethyl)-2-(2-pyridyl) benzimidazole in CDCl3 (49c)
Figure 23 : HRMS Spectrum of 1-(2-Pyridylmethyl)-2-(2-pyridyl) benzimidazole (49c)
-1
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.071.131.853.08
1.142.092.021.020.85
0.981.071.00
7.4 7.6
7.8 8.0
8.2 8.4
8.6 ppm
1.134
1.853
3.077
1.141
2.088
2.022
1.025
0.853
0.982
1.074
1.000
N
N N
N
Figure 24: 1H NMR Spectrum of 1-(2-quinolylmethyl)-2-(2-quinolyl) benzimidazole in CDCl3 (49d)
50 60
70 80
90 100 110
120 130
140 150
160
170 ppm
52.28
76.75
77.01
77.26
105.29
108.88
110.95
111.78
113.28
116.00
119.00
120.32
121.66
123.20
124.20
126.40
127.38
127.60
127.66
127.80
128.95
129.65
129.80
136.77
137.09
137.25
142.69
147.14
147.59
149.74
150.00
158.09
Figure 25: 13C NMR Spectrum of 1-(2-quinolylmethyl)-2-(2-quinolyl) benzimidazole in CDCl3 (49d)
50 60
70 80
90 100 110
120 130
140 150
160
170 ppm
52.28
110.95
119.00
120.32
121.67
123.20
124.20
126.41
127.39
127.60
127.66
128.95
129.65
129.80
136.77
137.09
Figure 26: Dept 135 Spectrum of 1-(2-quinolylmethyl)-2-(2-quinolyl) benzimidazole in CDCl3 (49d)
Figure 27: HRMS Spectrum of 1-(2-quinolylmethyl)-2-(2-quinolyl) benzimidazole (49d)
14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.00
2.001.93
2.17
2.40
2.00
1.17
6.0 6.1 6.2 6.3 6.4
6.5 ppm
2.000
1.997
1.932
7.2
7.3 ppm
2.167
2.399
N
N H N H N
H
1 H
2
3 4
4a
5 5a
6 7
8 9 4a
5 5a
6 7
8
9
Figure 28: 1H NMR Spectrum of N, N’- Bis (2-pyrrolylmethylidene)-1, 2-phenylenediamine in CDCl3 (48a)
200 180 160 140 120 100 80 60 40 20 0 ppm
76.6977.01
77.32
109.69
117.30118.97
123.88126.61
130.87
145.60
150.48
N
N H N H N
H
1 H
2
3 4
4a
5 5a
6 7
8 9 4a
5 5a
6 7
8
9
Figure 29: 13C NMR Spectrum of N, N’- Bis (2-pyrrolylmethylidene)-1, 2-phenylenediamine in CDCl3 (48a)
200 180 160 140 120 100 80 60 40 20 0 ppm
76.69
77.01
77.32
109.69
117.30
118.97
123.88
126.61
130.87
145.60
150.48
N
N H N H N
H
1 H
2
3 4
4a
5 5a
6 7
8 9 4a
5 5a
6 7
8
9
Figure 30: Dept 135 Spectrum of N, N’- Bis (2-pyrrolylmethylidene)-1, 2-phenylenediamine in CDCl3 (48a)
Figure 31: LRMS Spectrum of N, N’- Bis (2-pyrrolylmethylidene)-1, 2-phenylenediamine (48a)
9 8 7 6 5 4 3 2 1 0 ppm
0.601.000.510.942.081.85
N N N
N
S S
H H1
2
3 4'
3' 2'
1' 5'
4 5
6
3a 3
1
1' 2'
2 3'
4'
5'
3a 4 6
5 7 7
7a 7a
Figure 32: 1H NMR Spectrum of 2, 2-di-2-thienyl-5, 5’-Bi-1H-benzimidazole (52)
40 50 60 70 80 90 100 110 120 130 140 150 160
170 ppm
46.95
47.16
47.37
47.59
47.80
48.01
48.23
115.51
122.66
126.91
127.80
128.31
131.84
132.52
137.17
148.00
Figure 33: 13C NMR Spectrum of 2, 2-di-2-thienyl-5, 5’-Bi-1H-benzimidazole (52)
105 110
115 120
125 130
135 ppm
115.51
122.66
126.91
127.80
128.31
131.84
Figure 34: Dept 135 NMR Spectrum of 2, 2-di-2-thienyl-5, 5’-Bi-1H-benzimidazole (52)
Figure 35: HRMS Spectrum of 2, 2-di-2-thienyl-5, 5’-Bi-1H-benzimidazole (52)
-1
9 8 7 6 5 4 3 2 1 0 ppm
1.75
1.82
1.00
0.96
0.95
0.93
0.98
1.81
6.4 6.5 6.6 6.7
6.8 ppm
1.819
1.000
7.4 7.5 7.6 7.7 7.8
7.9 ppm
0.957
0.952
0.927
0.984
1.811
N N N
N
O O
O O
1
2
3 4'
3' 2'
1' 5'
4
5 6
3a 4a
6a
7 7a
9 11 10
8 8
9 10
11
7 7a
4a 3a 4
3 2 2' 1' 5' 4'
3'
5 6
Figure 36: 1H NMR Spectrum of 1, 2- di- 2-furanylmethyl-2, 2- di- 2-furanyl benzimidazole (53)
200 180 160 140 120 100 80 60 40 20 ppm
28.35
28.54
28.73
28.93
29.12
29.31
29.50
41.34
108.47
110.46
110.76
111.93
112.82
117.69
122.91
135.06
136.84
142.93
143.95
144.37
144.49
145.88
150.33
205.42
N N N
N
O O
O O
1
2
3 4'
3' 2'
1' 5'
4
5 6
3a 4a
6a
7 7a
9 11 10
8 8
9 10
11
7 7a
4a 3a 4
3 2 2'
1' 5' 4'
3'
5 6
Figure 37: 13C NMR Spectrum of 1, 2- di- 2-furanylmethyl-2, 2- di- 2-furanyl benzimidazole in acetone-d6 (53)
200 180 160 140 120 100 80 60 40 20 0 ppm
41.33
41.40
108.47
110.46110.76111.93
112.82117.69122.91
142.93144.49
205.41
N N N
N
O O
O O
1
2
3 4'
3' 2'
1' 5'
4
5 6
3a 4a
6a
7 7a
9 11 10
8 8
9 10
11
7 7a
4a 3a 4
3 2 2' 1' 5' 4'
3'
5 6
Figure 38: Dept 135 Spectrum 1, 2- di- 2-furanylmethyl-2, 2- di- 2-furanyl benzimidazole (53)
2931.4 cm-1
1421.8 cm-1
3101.2 cm-1
750.1 cm-1
1655.1 cm-1
0.02 0.04 0.06 0.08 0.10 0.12 0.14 0.16
4000 3500 3000 2500 2000 1500 1000
absorbance
wavenumber (cm-1)
Figure 39: IR Spectrum of 1, 2- di- 2-furanylmethyl-2, 2- di- 2-furanyl benzimidazole (53)
Figure 40: HRMS Spectrum of 1, 2- di- 2-furanylmethyl-2, 2- di- 2-furanyl benzimidazole (53)
-1
9 8 7 6 5 4 3 2 1 0 ppm
2.071.091.151.932.280.791.860.680.761.821.331.950.88
5.8 6.0 6.2 6.4
6.6 ppm
2.067
1.087
1.150
1.929
2.282
7.2 7.4 7.6
7.8 ppm
0.790
1.858
0.678
0.759
1.820
1.331
1.951
0.883
N N N
N
N N
N H
H H
Figure 41: 1H NMR Spectrum of 1, 2- di- 2-pyrrolylmethyl-2, 2- di- 2-pyrrolyl benzimidazole in methanol (54)
180 160 140 120 100 80 60 40 20 ppm
19.87
42.09
46.9647.17
47.38
47.5947.81
48.02
48.23
106.29106.44
107.68107.76
109.35109.72
110.32
111.07
115.92117.72
120.09121.42
121.79
121.98122.22
125.57125.98
128.36
142.71147.54
N N N
N
N N
N H
H H
Figure 42: 13C NMR Spectrum of 1, 2- di- 2-pyrrolylmethyl-2, 2- di- 2-pyrrolyl benzimidazole in methanol (54)
160 140 120 100 80 60 40 20 0 ppm
19.87
42.08
47.4547.6647.8848.09
48.30
106.29
106.44107.68107.75
109.34109.71110.31111.07
115.92115.97117.72
121.38121.97122.22125.56
128.36
N N N
N
N N
N H
H H
Figure 43: Dept 135 NMR Spectrum of 1, 2- di- 2-pyrrolylmethyl-2, 2- di- 2-pyrrolyl benzimidazole (54)
3063.9 cm-1
1599.1 cm-1
724.0 cm-1
1397.6 cm-1
0.02 0.04 0.06 0.08 0.10 0.12 0.14 0.16
4000 3500 3000 2500 2000 1500 1000
absorbance
wavenumber (cm-1)
Figure 44: IR Spectrum of 1, 2- di- 2-pyrrolylmethyl-2, 2- di- 2-pyrrolyl benzimidazole (54)
