ChemEx laboratory Vladimir Dal’ East Ukrainian National ...10.1007/s10593-014-1507... ·...

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


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


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)


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


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


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)


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


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)


8.107.72 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


8.107.72 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


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


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)


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


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)


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

ChemEx laboratory Vladimir Dal’ East Ukrainian National ...10.1007/s10593-014-1507... ·...

Documents

Transcript of ChemEx laboratory Vladimir Dal’ East Ukrainian National ...10.1007/s10593-014-1507... ·...