Chemistry of Heterocyclic Compounds, Vol. 50, No. 4, July, 2014 (Russian Original Vol. 50, No. 4, April, 2014)
V. V. Dotsenko, S. G. Krivokolysko
THE REACTION OF 3-ARYL-2-CYANOPROP-2-ENETHIOAMIDES WITH BROMONITROMETHANE: A NEW APPROACH TO
FUNCTIONALIZED 1,2,4-THIADIAZOLES
ChemEx laboratory, Vladimir Dal’ East Ukrainian National university, 20A Molodezhny kv., 91034 Lugansk, Ukraine е-mail: [email protected]
SUPPLEMENTARY INFORMATION
1
2
CONTENTS
1Н NMR spectrum (500 MHz, DMSO-d6) of (E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enethioamide (1e) .....3 1Н NMR spectrum (400 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis[3-(3,4-
dimethoxyphenyl)acrylonitrile] (14a) .................................................................................................4
LC–MS data for (2E,2'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis[3-(3,4-dimethoxyphenyl)acrylonitrile] (4a) .....5
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis[3-(3,4-dimethoxyphenyl)acrylonitrile] (4a) ...6
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis[3-(2-chlorophenyl)acrylonitrile] (4b).............7 1Н NMR spectrum (300 MHz, DMSO-d6) of (2E,2'E)- 2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(5-nitro-2-
furyl)acrylonitrile] (4c) .......................................................................................................................8 1Н NMR spectrum (400 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-
hydroxyphenyl)acrylonitrile] (4e) .......................................................................................................9
LC–MS (ES-API) data for (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxyphenyl)acrylonitrile] (4e)10
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxyphenyl)acrylonitrile] (4e)..........11 1Н NMR spectrum (500 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-3-
methoxyphenyl)-acrylonitrile] (4f) ...................................................................................................12 13C NMR spectrum (126 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-3-
methoxyphenyl)-acrylonitrile] (4f) ...................................................................................................13 13C APT NMR spectrum (126 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-
3-methoxyphenyl)acrylonitrile] (4f) .................................................................................................14
LC–MS (ES-API) data for (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)acrylonitrile] (4f).....................................................................................................15
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)acrylonitrile] (4f).....................................................................................................................................................16
1Н NMR spectrum (400 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(2-furyl)acrylonitrile] (4g) .....................................................................................................................17
13C NMR spectrum (126 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(2-furyl)acrylonitrile] (4g) .....................................................................................................................18
LC–MS (ES-API) data for (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(2-furyl)acrylonitrile] (4g) ............19
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(2-furyl)acrylonitrile] (4g) ..........................20
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-methoxyphenyl)acrylonitrile] (4h).........21 1Н NMR spectrum (500 MHz, DMSO-d6) of 1,2,4-thiadiazol-3,5-diyl-bis{[(E)-2-cyanoethen-2,1-diyl]-4,1-
phenylene}dibenzoate (4i) ................................................................................................................22
FTIR spectrum of 1,2,4-thiadiazol-3,5-diyl-bis{[(E)-2-cyanoethen-2,1-diyl]-4,1-phenylene}dibenzoate (4i)23 1Н NMR spectrum (500 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-
nitrophenyl)acrylonitrile] (4k) ..........................................................................................................24 13C NMR spectrum (126 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-
nitrophenyl)acrylonitrile] (4k) ..........................................................................................................25
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-nitrophenyl)acrylonitrile] (4k) ...............26 1Н NMR spectrum (500 MHz, DMSO-d6) of (2E,4E,2'E,4'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis(5-
phenylpenta-2,4-dienenitrile) (4l) .....................................................................................................27 13C NMR spectrum (126 MHz, DMSO-d6) of (2E,4E,2'E,4'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis(5-
phenylpenta-2,4-dienenitrile) (4l) .....................................................................................................28
FTIR spectrum of of (2E,4E,2'E,4'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis(5-phenylpenta-2,4-dienenitrile) (4l)29
3
1Н NMR spectrum (500 MHz, DMSO-d6) of (E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enethioamide (1e)
11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5Chemical Shift (ppm)
2.082.021.00 0.98 0.97
water
DMSO-d6
10.6
058
9.90
66
9.38
73
8.02
907.
8803
7.86
37
6.93
476.
9171
3.38
58
2.49
00
8.1 8.0 7.9 7.8Chemical Shift (ppm)
2.021.01
8.02
90
7.88
037.
8637
7.00 6.95 6.90 6.85Chemical Shift (ppm)
2.08
6.93
476.
9171
NH2
S
OHCN
4
1Н NMR spectrum (400 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis[3-(3,4-dimethoxyphenyl)acrylonitrile] (4a)
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5Chemical Shift (ppm)
10.662.72 2.132.00
DMSO-d6
water
2.49
002.
4926
2.52
89
3.25
07
3.84
243.
8720
3.89
04
7.15
297.
1742
7.19
507.
2160
7.66
637.
6870
7.75
617.
7727
8.44
228.
4721
7.8 7.7 7.6 7.5 7.4 7.3 7.2 7.1Chemical Shift (ppm)
2.72 2.131.13
7.15
297.
1742
7.19
507.
2160
7.66
637.
6870
7.75
617.
7727
3.95 3.90 3.85 3.80Chemical Shift (ppm)
10.66
3.84
24
3.87
203.
8904
CNN
N S
NC OMeMeO
OMeMeO
5
LC–MS data for (2E,2'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)-bis[3-(3,4-dimethoxyphenyl)acrylonitrile] (4a)
6
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis[3-(3,4-dimethoxyphenyl)acrylonitrile] (4a)
3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600Wavenumber (cm-1)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
0.55
0.60
0.65
0.70
0.75
0.80Tr
ansm
ittan
ce
3605.17 3532.033474.293462.743431.94
3408.84
3004.632960.36
2933.41
2833.32
2606.2
2282.83
2213.53
1584.121568.72
1510.981462.86
1449.381424.36
1382.021368.54
1341.59
1274.231266.53
1220.331201.08
1166.441145.26
1099.07 1085.591035.55
1018.23981.65
933.53 918.14850.77 802.65
777.62 729.5716.03
623.64579.37 571.67
558.2
S N
N
N
N
MeO
MeO OMe
OMe
7
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis[3-(2-chlorophenyl)acrylonitrile] (4b)
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 400Wavenumber (cm-1)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
0.55
0.60
0.65
0.70
0.75
0.80
0.85
Tran
smitt
ance
3426.17
3062.383033.5
2916.09
2846.8
2217.38
1584.121576.42
1478.261439.76
1418.591355.07
1306.9512801208.78
1187.611127.94
1093.291052.87
1039.4
920.06
846.92
760.3741.05
708.33681.38
590.92579.37
S N
N
N
NCl
Cl
8
1Н NMR spectrum (300 MHz, DMSO-d6) of (2E,2'E)- 2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(5-nitro-2-furyl)acrylonitrile] (4c)
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5Chemical Shift (ppm)
2.05 2.021.021.00
water
DMSO-d6
8.59
21
8.46
06
7.88
807.
8821
7.87
637.
8558 7.67
767.
6645
7.64
84
3.30
66
2.49
00
8.6 8.5 8.4 8.3 8.2 8.1 8.0 7.9 7.8 7.7 7.6Chemical Shift (ppm)
2.05 2.021.02 1.00
8.59
21
8.46
06
7.88
807.
8821
7.87
637.
8558
7.67
76 7.66
457.
6484
CNN
N S
NC
O
O
N+O
O
N+
OO
9
1Н NMR spectrum (400 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxyphenyl)acrylonitrile] (4e)
11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0Chemical Shift (ppm)
4.013.932.001.03 0.99
water
DMSO-d6
10.8
820
10.6
254
8.45
708.
4290
8.05
178.
0309
7.99
387.
9725
6.99
826.
9762
6.96
976.
9471
3.34
05
2.52
892.
4900
8.50 8.45 8.40 8.35 8.30 8.25 8.20 8.15 8.10 8.05 8.00 7.95Chemical Shift (ppm)
3.932.00
8.45
70
8.42
90
8.05
17
8.03
09
7.99
38
7.97
25
7.10 7.05 7.00 6.95 6.90Chemical Shift (ppm)
4.01
6.99
82 6.97
626.
9697
6.94
71
CNN
N S
NCOH
OH
10
LC–MS (ES-API) data for (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxyphenyl)acrylonitrile] (4e)
11
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxyphenyl)acrylonitrile] (4e)
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 400Wavenumber (cm-1)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
0.55
0.60
0.65
0.70
0.75
Tran
smitt
ance
3345.32
3154.77
3020.03
2810.232744.78
2604.27
2457.99
2354.052336.72
2221.23
2132.69
2022.98
1868.99
1668.811609.14
1582.21570.65
1516.75
1439.761374.32
1360.841328.12
1283.851239.58
1208.781179.911168.36
1112.541085.59
1018.23998.98
962.41927.76
906.59848.84
827.67806.5
773.77733.35
717.96662.14
654.44602.47
562.05548.57
521.62513.92
490.83473.5454.26S N
N
N
N
OH
OH
12
1Н NMR spectrum (500 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)acrylonitrile] (4f)
10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5Chemical Shift (ppm)
6.042.001.981.95 0.960.92 0.92
DMSO-d6
10.5
531
10.2
552
8.39
908.
3620
7.75
057.
7329
7.66
117.
6446
7.56
147.
5450
6.98
226.
9654
6.95
016.
9336
3.83
72
3.35
09
2.49
00
CNN
N S
NCOH
OH
OMeMeO
8.5 8.4 8.3 8.2 8.1 8.0 7.9 7.8 7.7 7.6 7.5 7.4 7.3 7.2 7.1 7.0 6.9 6.8Chemical Shift (ppm)
2.001.981.95 0.960.96
8.39
908.
3620
7.75
057.
7329
7.66
117.
6446
7.56
147.
5450 6.
9822
6.96
546.
9501
6.93
36
13
13C NMR spectrum (126 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)acrylonitrile] (4f)
CNN
N S
NCOH
OH
OMeMeO
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40Chemical Shift (ppm)
DMSO-d6
184.
53
168.
87
152.
6415
1.40
150.
1014
9.65
147.
8514
7.76
126.
7912
5.78
123.
5812
3.29
116.
9611
6.57
116.
1511
5.91
113.
9111
3.26
99.3
8
96.1
9
55.5
5
39.5
0
155 154 153 152 151 150 149 148 147 146Chemical Shift (ppm)
152.
64
151.
40
150.
10
149.
65 147.
8514
7.76
128 127 126 125 124 123 122 121 120 119 118 117 116 115 114 113 112Chemical Shift (ppm)
126.
79
125.
78
123.
5812
3.29
116.
96
116.
57 116.
1511
5.91
113.
91
113.
26
14
13C APT NMR spectrum (126 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)acrylonitrile] (4f)
CNN
N S
NCOH
OH
OMeMeO
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40Chemical Shift (ppm)
DMSO-d618
4.50
168.
84
152.
6315
1.38
150.06149.62
147.
8414
7.75
126.76125.74
123.
5712
3.27
116.
9111
6.52
116.14115.90113.93
113.28
99.3
9
96.1
9
55.55
40.0
039
.83
39.6
739
.50
39.3
339
.17
39.0
0
153 152 151 150 149 148Chemical Shift (ppm)
152.
63
151.
38
150.06
149.62
147.
8414
7.75
126 124 122 120 118 116 114Chemical Shift (ppm)
126.76
125.74
123.
5712
3.27
116.
9111
6.52
116.14115.90
113.93113.28
15
LC–MS (ES-API) data for (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)acrylonitrile] (4f)
16
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)acrylonitrile] (4f)
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 400Wavenumber (cm-1)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
0.55
0.60
0.65
0.70
0.75Tr
ansm
ittan
ce
3497.38 3395.37
2998.862948.81
2918.02
2829.47
2207.76
1566.81509.05
1462.861428.21
1383.941297.321283.85
1256.91204.93
1168.361133.71
1091.371027.85
1004.75964.33
923.91885.41
846.92808.42
758.38719.88
629.41
556.27537.02506.23
S N
N
N
N
OH
OH
OMe
MeO
17
1Н NMR spectrum (400 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(2-furyl)acrylonitrile] (4g)
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5Chemical Shift (ppm)
1.06 1.031.02 0.99
water
DMSO
8.41
958.
3562
8.29
088.
1922
7.54
447.
5361
7.48
737.
4790
6.93
606.
9319
6.88
416.
8799
3.34
30
2.51
042.
4263
7.55 7.50 7.45 7.40 7.35 7.30 7.25 7.20 7.15 7.10 7.05 7.00 6.95 6.90 6.85Chemical Shift (ppm)
1.03 1.020.99 0.97
7.54
447.
5361
7.48
737.
4790
6.93
606.
9319
6.92
676.
8841
6.87
996.
87588.5 8.4 8.3 8.2
Chemical Shift (ppm)
1.06 1.021.00 1.00
8.41
95
8.35
62
8.29
08
8.19
22
CNN
N S
NC
O
O
18
13C NMR spectrum (126 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(2-furyl)acrylonitrile] (4g)
CNN
N S
NC
O
O
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40Chemical Shift (ppm)
DMSO-d618
3.92
168.
25
150.
10
148.
36
134.
4413
4.28
124.
42
121.
6011
5.75
115.
5711
4.53
113.
97
99.0
1
95.8
0
40.0
940
.00
39.8
339
.67
39.5
039
.33
39.1
639
.00
152 150 148 146 144 142 140 138 136 134 132 130 128 126 124 122 120 118 116 114Chemical Shift (ppm)
150.
1014
8.63
148.
4714
8.36
134.
4413
4.28
124.
42
121.
60
115.
75 115.
57 114.
5311
3.97
19
LC–MS (ES-API) data for (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(2-furyl)acrylonitrile] (4g)
20
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(2-furyl)acrylonitrile] (4g)
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 400Wavenumber (cm-1)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
0.55
0.60
0.65
Tran
smitt
ance
3435.79
3127.823106.65
3052.753023.88
2217.38
1612.991587.97
1532.151482.11
1462.861435.91
1397.411385.871343.52
1316.571293.47
1278.081254.98
1201.081181.83
1149.111091.37 1079.82
1029.77
943.16927.76 879.64
835.37823.82
777.62760.3
752.6735.28
710.26665.99648.66
592.84583.22
542.8
S N
N
N
N
O O
21
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-methoxyphenyl)acrylonitrile] (14h)
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 400Wavenumber (cm-1)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
0.55
0.60
0.65
Tran
smitt
ance
3437.72
3068.15
3004.63
2935.34
2829.47
2217.38
2022.98
1605.291591.82
1561.021510.98
1472.48
1331.971308.87
1266.531187.61
1176.06
1027.851020.15
821.9S N
N
N
N
MeO
OMe
22
1Н NMR spectrum (500 MHz, DMSO-d6) of 1,2,4-thiadiazol-3,5-diyl-bis{[(E)-2-cyanoethen-2,1-diyl]-4,1-phenylene}dibenzoate (14i)
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5Chemical Shift (ppm)
8.107.72 2.081.79
water
DMSO-d6
8.66
36
8.23
438.
2167
8.19
918.
1815 8.
1659
8.15
127.
7835
7.77
28
7.64
27 7.62
707.
6104
7.60
067.
5928
7.57
237.
5547
3.27
23
2.49
00
8.7 8.6 8.5 8.4 8.3 8.2 8.1 8.0 7.9 7.8 7.7 7.6 7.5Chemical Shift (ppm)
8.107.72 2.081.79
8.66
36
8.23
438.
2167
8.19
918.
1815
8.16
598.
1512
7.78
357.
7728
7.75
71
7.64
277.
6270
7.61
047.
5928
7.57
237.
5547
CNN
N S
NC OO
OO
23
FTIR spectrum of 1,2,4-thiadiazol-3,5-diyl-bis{[(E)-2-cyanoethen-2,1-diyl]-4,1-phenylene}dibenzoate (4i)
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 400Wavenumber (cm-1)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
0.55
0.60
0.65
0.70
0.75Tr
ansm
ittan
ce
3431.94
3052.753025.81
2921.87
2848.72
2219.31
1734.26
1591.821561.02
1505.21470.56
1449.381418.59
1358.921310.8
1264.61222.261166.44
1116.391075.97
1058.651022.08
998.98935.46
870.02850.77 812.27
793.02714.11
696.78673.68
602.47
519.7
S N
N
N
N
O
OO
O
24
1Н NMR spectrum (500 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-nitrophenyl)acrylonitrile] (4k)
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0Chemical Shift (ppm)
4.301.00
water
DMSO-d6
8.77
128.
7229
8.44
628.
4287
8.41
338.
2903 8.
2750
8.26
07
3.31
78
2.52
842.
4900
8.85 8.80 8.75 8.70 8.65 8.60 8.55 8.50 8.45 8.40 8.35 8.30 8.25Chemical Shift (ppm)
4.304.131.000.92
8.77
12
8.72
29
8.44
62 8.42
87
8.41
33
8.39
57
8.29
03
8.27
508.
2607
S N
N
N
N
N+
O
O
N+
O
O
25
13C NMR spectrum (126 MHz, DMSO-d6) of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-nitrophenyl)acrylonitrile] (4k)
S N
N
N
N
N+
O
O
N+
O
O
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40Chemical Shift (ppm)
DMSO-d6
186.
2416
183.
8420
167.
6083
149.
0941
148.
7253
147.
5354
138.
1871
137.
7032
131.
4723
131.
1351
124.
3331
124.
1745
115.
3695
114.
8975
107.
5243
105.
1010
39.5
000
149 148 147 146 145 144 143 142 141 140 139 138 137Chemical Shift (ppm)
149.
0941
148.
7253
147.
5473
147.
5354
138.
1871
137.
7032
132 130 128 126 124 122 120 118 116 114 112 110 108 106 104Chemical Shift (ppm)
131.
4723
131.
1351
124.
3331
124.
1745
115.
3695
114.
8975
107.
5243
105.
1010
26
FTIR spectrum of (2E,2'E)-2,2'-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-nitrophenyl)acrylonitrile] (4k)
S N
N
N
N
N+
O
O
N+
O
O
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 400Wavenumber (cm-1)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
0.55
0.60
Tran
smitt
ance
3576.33553.2 3431.94
3106.653083.55
2923.79
2846.8
2221.23
1603.371587.97
1555.251509.05
1468.631420.51
1370.471343.52
1281.931231.88
1206.861179.91
1114.471087.52
1008.6962.41 939.31
918.14858.47
846.92818.05
793.02748.75
683.31654.44
602.47558.2
488.9
27
1Н NMR spectrum (500 MHz, DMSO-d6) of (2E,4E,2'E,4'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis(5-phenylpenta-2,4-dienenitrile) (4l)
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0Chemical Shift (ppm)
6.37 6.312.00
waterDMSO-d6
8.37
058.
3485
8.32
338.
3002
7.72
827.
7018
7.68
987.
6601
7.47
247.
4471
7.33
627.
3099
7.28
46
3.20
80
2.52
952.
4900
7.8 7.7 7.6 7.5 7.4 7.3Chemical Shift (ppm)
6.37 6.31 2.05
7.72
827.
7018
7.68
98
7.66
01
7.62
39
7.59
31
7.47
247.
4471
7.36
26 7.33
627.
3099
7.28
46
8.40 8.35 8.30 8.25Chemical Shift (ppm)
2.00
8.37
05
8.34
85
8.32
33
8.30
02
S N
N
N
N
28
13C NMR spectrum (126 MHz, DMSO-d6) of (2E,4E,2'E,4'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis(5-phenylpenta-2,4-dienenitrile) (4l)
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40Chemical Shift (ppm)
DMSO-d618
3.17
97
167.
8900
151.
6325
150.
1650
149.
2091
146.
8254
135.
0260
134.
7325
131.
2224
129.
2274
128.
6840
128.
2398
123.
3019
123.
1829
115.
0522
114.
3859
104.
9463
102.
2533
39.5
000
134 132 130 128 126 124 122 120 118 116Chemical Shift (ppm)
135.
0260
134.
7325
131.
2224
130.
6077
129.
2274
129.
1283
128.
6840
128.
2398
123.
3019
123.
1829
115.
0522
114.
3859
S N
N
N
N
29
FTIR spectrum of of (2E,4E,2'E,4'E)-2,2'-(1,2,4-thiadiazole-3,5-diyl)bis(5-phenylpenta-2,4-dienenitrile) (4l)
S N
N
N
N
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 400Wavenumber (cm-1)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
0.55
0.60
0.65
0.70
0.75
Tran
smitt
ance
3441.573431.94
3073.933054.68
3021.962996.93
2918.022846.8 2215.46
1609.141601.44
1574.5
1468.63
1420.511366.62
1310.81301.17
1283.851249.2
1212.631160.66
1074.051024
966.26943.16 881.56854.62
821.9
746.83731.43
683.31650.59 606.32
529.32498.53
469.65
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