template for submission of notes to€¦ · supporting information . metathetic sulfur transfer...
TRANSCRIPT
Supporting information
Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-
thione derivatives: a route to diversely substituted S-alkyl carbamothioates
Abdallah Larbi Doukara , Mohammed Amine Mehdid, Ayada Djafri, Federico Andreoli,
Nicolas Vanthuyne, Christian Roussel*
Chirosciences, ISM2, Université Paul Cézanne Aix-Marseille III 13397 Marseille CEDEX 20 France
Table of contents
1) 1H and 13C NMR spectra (SI-2—SI-34)
SI-1
ppm (t1)0.01.02.03.04.05.06.07.08.09.0
0
50000
10000
9.07
0
8.14
18.
113
7.66
0
7.49
87.
440
7.30
67.
188
7.18
07.
060
6.92
96.
925
2.50
0
2.23
2
1.84
61.
844
1.00
0.960.88
0.95
0.88
2.98
2.94
6.28
ppm (t1)050100150200
0
10000
20000
30000
40000
50000
60000
70000
80000189.
177
152.
281
140.
003
136.
765
135.
959
130.
898
129.
958
129.
248
129.
083
127.
496
123.
547
122.
635
118.
234
107.
853
39.5
20
20.3
26
14.9
54
NHN
HN
O
S
S
300 MHz, DMSO-d6
NHN
HN
O
S
S3b
75 MHz, DMSO-d6
3b
SI-2
ppm (t1)0.01.02.03.04.05.06.07.08.0
0
10000
20000
30000
40000
500008.
308
8.16
88.
142
7.72
27.
461
7.33
6
7.26
07.
241
7.21
37.
180
7.14
9
6.90
86.
857
6.65
76.
654
1.92
31.
921
0.931.00
2.07
1.070.981.650.99
1.02
1.00
3.03
300 MHz, CDCl3
ppm (t1)50100150
0
50000
10000
15000
189.
867
151.
397
141.
418
140.
310
135.
330
132.
456
132.
017
131.
577
131.
293
131.
136
128.
631
128.
346
126.
943
125.
018
124.
825
123.
529
121.
404
118.
102
118.
062
117.
790
115.
575
115.
523
115.
472
110.
120
77.0
00
15.3
07
NHN
HN
O
S
S
CF3
CF3
3c
NHN
HN
O
S
S
CF3
CF3
3c 75 MHz, CDCl3
SI-3
ppm (t1)0.05.010.0
0
50000
9.83
1
8.20
88.
162
8.09
18.
051
7.92
67.
666
7.62
07.
562
7.47
67.
325
7.32
0
7.22
2
6.94
26.
936
2.50
0
1.85
71.
852
10000
0.98
2.011.010.99
2.030.962.04
1.00
3.08
S
ppm (t1)050100150
0
50000
189.
114
151.
923
145.
905
141.
221
139.
985
135.
125
130.
122
129.
196
128.
396
125.
199
124.
638
123.
478
117.
542
107.
953
39.5
20
15.0
02
N
3d S
200 MHz, DMSO-d6 HN
HN
ONO2
NHN
HN
ONO2
S
S
3d
75 MHz, DMSO-d6
SI-4
ppm (t1)1.02.03.04.05.06.07.08.0
0
50000
10000
15000
20000
25000
30000
35000
8.07
18.
044
7.98
17.
942
7.70
87.
455
7.39
77.
376
7.16
27.
152
7.14
37.
140
6.87
46.
870
4.52
74.
507
4.47
24.
464
4.45
34.
445
4.41
04.
391
2.50
0
1.81
11.
808
0.92
1.85
1.97
1.00
2.94
2.25
4.13
NHN
S
HN
O
S
CF3
CF3
3e
300 MHz, DMSO-d6
ppm (t1)050100150
0
50000
10000
189.
175
155.
153
144.
056
139.
937
136.
339
130.
832
130.
399
129.
966
129.
879
129.
533
129.
032
128.
801
127.
850
127.
810
127.
246
125.
185
123.
208
122.
484
121.
571
120.
579
120.
528
120.
479
117.
956
107.
645
41.9
3439
.520
14.8
01
NHN
S
HN
O
S
CF3
CF3
3e
75 MHz, DMSO-d6
SI-5
ppm (t1)0.01.02.03.04.05.06.07.08.0
0
50000
8.20
68.
179
7.42
17.
363
7.32
6
7.09
07.
078
6.90
06.
896
6.73
26.
707
3.74
83.
637
2.50
0
1.81
01.
807
1.08
71.
065
1.05
31.
031
3.00
1.03
6.17
0.951.001.94
1.00
2.03
NHN
S
S
HN
O
3f
300 MHz, DMSO-d6
ppm (t1)050100150
0
50000
10000
15000
20000
25000
30000
189.
209
154.
120
140.
029
136.
873
129.
812
128.
982
126.
282
122.
355
121.
344
107.
706
41.0
82
39.5
20
22.8
9622
.852
14.8
70
NHN
S
S
HN
O
75 MHz, DMSO-d6
3f
SI-6
ppm (t1)1.02.03.04.05.06.07.08.0
0
10000
20000
30000
40000
50000
7.98
97.
982
7.94
87.
941
7.54
07.
532
7.46
27.
454
7.29
07.
283
7.26
07.
080
7.07
36.
729
6.36
16.
355
3.49
3
3.42
03.
405
3.33
23.
305
1.93
81.
932
1.72
6
1.67
0
1.52
61.
499
1.01
1.05
1.351.02
0.96
1.00
4.25
3.11
8.39
NHN
S
S
N
O
200 MHz, CDCl3 3g
ppm (t1)050100150
0
50000
10000
15000
20000
25000
30000
35000
188.
635
154.
813
141.
078
136.
023
130.
587
129.
563
127.
324
126.
226
124.
844
106.
748
77.0
00
46.8
80
28.2
98
26.9
24
16.0
65
75 MHz, CDCl3
NHN
S
S
N
O
3g
SI-7
ppm (t1)0.01.02.03.04.05.06.07.08.09.0
0
50000
10000
15000
20000
25000
30000
350007.53
7
7.45
97.
451
7.27
87.
260
7.19
57.
076
7.06
86.
765
6.36
36.
358
3.46
93.
359
3.21
73.
108
1.93
81.
932
1.14
61.
110
1.07
4
1.00
0.92
1.011.34
1.04
4.29
3.11
6.27
0.99
NHN
S
S
N
O
3h
200 MHz, CDCl3
ppm (t1)050100150
0
10000
20000
30000
40000
188.
596
154.
264
141.
065
136.
038
130.
586
129.
161
127.
310
125.
777
124.
603
106.
808
77.0
00
41.6
50
16.0
9513
.681
75 MHz, CDCl3
NHN
S
S
N
O
3h
SI-8
ppm (t1)0.01.02.03.04.05.06.07.08.0
0
10000
20000
30000
400008.
025
7.99
47.
516
7.45
97.
260
7.25
3
7.19
77.
096
7.06
56.
744
6.36
36.
359
3.32
93.
279
3.22
93.
112
3.06
13.
011
1.92
31.
919
1.61
11.
566
1.50
9
1.45
21.
408
0.91
40.
890
0.86
5
0.96
0.96
1.270.94
1.05
1.00
1.952.06
3.09
4.39
5.35
NHN
S
S
N
O
300 MHz, CDCl3
3i
ppm (t1)050100150200
0
50000
10000
15000
20000
25000188.
627
154.
632
141.
036
136.
093
130.
561
129.
027
127.
286
125.
735
124.
548
106.
761
77.0
00
49.3
40
21.6
8116
.078
11.2
00
75 MHz, CDCl3
NHN
S
S
N
O
3i
SI-9
ppm (t1)1.02.03.04.05.06.07.08.0
0
10000
20000
30000
40000
50000
60000
700008.
082
8.05
07.
865
7.86
17.
753
7.69
6
7.54
1
7.23
97.
051
7.00
2
3.31
0
2.97
3
2.29
82.
295
1.021.001.041.073.232.18
1.05
2.96
3.09
ppm (t1)050100150
0
50000
10000
15000
20000
181.
992
154.
277
148.
341
139.
852
136.
253
134.
163
129.
914
129.
010
127.
217
126.
858
126.
499
124.
345
120.
300
118.
073
49.0
00
18.3
9814
.288
N+
HN
HN
O
S
SI-
300 MHz, CD3OD
1a
N+
HN
HN
O
S
SI-
1a 75 MHz, CD3OD
SI-10
ppm (t1)1.02.03.04.05.06.07.08.0
-10000
0
10000
20000
30000
40000
50000
60000
70000
80000
8.05
38.
049
8.02
58.
021
7.85
67.
852
7.74
9
7.69
17.
523
7.40
17.
236
7.07
2
3.31
0
2.96
4
2.30
32.
300
2.27
6
1.000.951.05
2.16
1.972.06
5.95
2.86
300 MHz, CD3OD
N+
HN
HN
O
S
SI-
1b
ppm (t1)050100150200
0
500
1000
1500
2000
181.
890
165.
397
148.
467
139.
423
137.
128
136.
380
134.
185
130.
378
128.
946
126.
808
126.
423
120.
616
117.
888
111.
002
49.0
00
20.7
8018
.280
14.2
60
N+
HN
HN
O
S
SI-
1b
75 MHz, CD3OD
SI-11
ppm (t1)5.010.0
0
50000
10000
15000
20000
25000
30000
9.44
6
8.59
88.
114
8.09
58.
070
8.04
68.
044
7.74
17.
707
7.68
57.
648
7.62
9
7.46
47.
431
2.92
8
2.50
0
2.20
72.
205
3.04
3.00
0.98
1.00
1.023.01
3.93
500 MHz, CD3OD
ppm (t1)050100150
0
50000
10000
179.
720
152.
102
145.
796
141.
049
134.
217
132.
671
131.
141
130.
881
130.
621
130.
361
128.
108
126.
423
125.
585
125.
355
124.
707
124.
254
122.
084
119.
918
118.
097
115.
020
114.
994
114.
971
39.5
20
17.9
8013
.655
N+
HN
HN
O
S
S
CF3
CF3
I-1c
125 MHz, CD3OD
N+
HN
HN
O
S
S
CF3
CF3
I-1c
SI-12
ppm (t1)1.02.03.04.05.06.07.08.09.0
0
10000
20000
30000
40000
500009.
470
8.53
3
8.19
98.
180
8.10
78.
105
8.09
08.
040
8.03
87.
747
7.74
47.
713
7.65
27.
629
7.62
6
7.46
27.
432
7.42
9
2.93
1
2.50
0
2.21
32.
211
1.17
1.13
1.093.151.12
3.36
3.30
4.00
500 MHz, DMSO-d6
HN
HN
O
N+
S
S
NO2
I-
1d
ppm (t1)50100150
0
10000
20000
30000
40000
50000
60000
70000
80000
179.
728
151.
703
145.
941
145.
453
141.
479
134.
321
132.
735
128.
092
125.
575
125.
316
125.
134
124.
511
117.
953
117.
805
39.5
20
17.8
6313
.680
125 MHz, DMSO-d6
HN
HN
O
N+
S
S
NO2
I-
1d
SI-13
ppm (t1)1.02.03.04.05.06.07.08.0
0
50000
10000
15000
20000
25000
30000
7.93
27.
883
7.76
57.
761
7.72
1
7.66
3
7.51
97.
514
7.48
77.
441
7.43
67.
390
7.38
5
4.52
04.
466
4.46
04.
406
3.31
0
2.93
8
2.24
42.
240
3.05
3.04
2.20
2.09
1.041.004.03
ppm (t1)50100150200
0
50000
10000
15000
20000
25000
30000
35000
181.
812
157.
146
148.
248
144.
528
136.
396
134.
113
133.
384
132.
942
132.
504
132.
065
130.
281
129.
005
128.
956
128.
905
127.
535
126.
920
126.
855
126.
673
123.
070
121.
945
121.
893
121.
842
117.
813
49.0
00
43.7
46
18.3
9814
.233
300 MHz, CD3OD
HN
HN
O
N+
S
S
CF3
CF3
I-
1e
HN
HN
O
N+
S
S
CF3
CF3
I-1e
75 MHz, CD3OD
SI-14
ppm (t1)1.02.03.04.05.06.07.08.0
0
50000
10000
8.05
48.
022
7.86
17.
857
7.75
0
7.69
2
7.54
17.
509
7.46
2
7.39
57.
370
7.36
6
7.28
97.
236
7.04
97.
000
3.53
23.
529
3.50
83.
504
3.48
33.
480
3.45
83.
455
3.31
0
2.29
82.
294
1.54
61.
521
1.49
6
1.021.001.031.12
2.26
1.03
2.22
3.15
2.95
1.022.25
ppm (t1)50100150200
0
10000
20000
30000
180.
19
154.
2714
8.04
139.
87
136.
1413
4.09
129.
9012
9.03
127.
5012
6.89
126.
6412
4.33
120.
3011
8.12
49.0
0
31.8
3
14.3
513
.27
300 MHz, CD3OD S
N+
HN
HN
O
S 1f I-
75 MHz, CD3OD
N+
HN
HN
O
S
SI-
1f
SI-15
ppm (t1)1.02.03.04.05.06.07.08.09.0
0
10000
20000
30000
40000
50000
60000
700008.
689
8.16
28.
147
8.14
38.
119
8.11
58.
075
8.07
17.
701
7.64
47.
597
7.56
67.
382
7.32
77.
282
7.25
4
7.09
47.
066
3.48
73.
462
3.43
8
2.50
02.
231
2.19
82.
194
1.43
01.
406
1.38
12.011.00
1.00
2.20
1.172.062.06
2.06
5.93
3.14
300 MHz, DMSO-d6
N+
HN
HN
O
S
SI-
1g
ppm (t1)050100150200
0
50000
177.
866
151.
946
145.
852
136.
267
135.
023
132.
580
131.
422
129.
286
127.
949
124.
548
124.
533
123.
665
118.
601
118.
124
39.5
20
30.0
89
20.3
52
13.7
0412
.926
N+
HN
HN
O
S
SI-
1g
75 MHz, DMSO-d6
SI-16
ppm (t1)1.02.03.04.05.06.07.0
7.89
57.
879
7.86
47.
750
7.74
67.
720
7.66
2
7.51
07.
389
4.52
0
4.45
64.
451
4.39
5
3.48
33.
458
3.43
33.
409
3.31
0
2.25
22.
248
1.51
91.
495
1.47
0
8.0
0
50000
10000
4.041.000.96
2.17
1.91
2.03
3.06
3.101h
S CF3
ppm (t1)050100150
0
10000
20000
30000
40000179.
994
157.
124
148.
058
144.
541
136.
347
134.
083
132.
948
132.
511
129.
009
128.
959
127.
879
126.
977
126.
931
126.
678
123.
076
121.
970
121.
920
121.
868
117.
733
49.0
00
43.7
76
31.7
75
14.2
9213
.273
HN
HN
O
N+ S
CF3
I-
300 MHz, CD3OD
HN
HN
O
N+
S
S
CF3
CF3
I-
1h
75 MHz, CD3OD
SI-17
ppm (t1)1.02.03.04.05.06.07.08.0
0
50000
10000
7.97
57.
943
7.85
87.
855
7.69
6
7.63
8
7.49
77.
465
7.39
7
7.34
1
3.85
13.
829
3.80
73.
785
3.76
33.
742
3.72
03.
525
3.50
03.
476
3.45
1
3.31
0
2.26
12.
257
1.55
31.
528
1.50
3
1.14
21.
123
1.12
01.
102
6.29
3.20
3.20
2.21
1.12
1.151.071.101.000.92
ppm (t1)050100150200
0
10000
20000
30000
40000
50000
60000
70000
179.
503
155.
663
147.
368
136.
027
133.
352
128.
300
126.
370
125.
624
125.
492
117.
447
42.5
74
31.1
58
22.4
99
13.6
6812
.688
N+
HN
S
S
HN
O
I-1i
300 MHz, CD3OD
N+
HN
S
S
HN
O
I-1i
75 MHz, CD3OD
SI-18
ppm (t1)1.02.03.04.05.06.07.08.09.0
0
50000
10000
8.02
88.
000
7.84
87.
845
7.75
37.
747
7.69
5
7.53
17.
504
7.46
37.
439
7.41
27.
387
7.35
4
7.28
77.
234
7.04
97.
000
3.48
53.
432
3.31
0
2.30
42.
301
1.91
81.
819
1.50
01.
456
1.30
61.
257
0.91
00.
889
0.86
6
1.031.001.04
4.372.30
1.09
1.99
2.02
14.39
3.23
ppm (t1)050100150
0
50000
10000
15000
20000
25000
30000
180.
339
154.
219
148.
140
139.
888
136.
140
134.
110
129.
920
129.
004
127.
578
126.
931
126.
691
124.
330
120.
268
117.
981
49.0
0037
.316
33.0
2430
.599
30.4
8230
.373
30.0
7129
.744
28.9
05
23.7
06
14.4
2214
.370
HN
HN
O
N+
S
S1j I-
300 MHz, CD3OD
HN
HN
O
N+
S
SI-
1j
75 MHz, CD3OD
SI-19
ppm (t1)0.01.02.03.04.05.06.07.08.09.0
0
50000
10000
15000
20000
25000
30000
9.19
7
8.49
68.
374
8.33
68.
332
7.67
27.
664
7.61
67.
611
7.48
27.
260
7.19
57.
189
7.07
07.
063
7.00
6
3.66
13.
533
3.37
23.
243
2.25
82.
239
2.23
61.
943
1.84
5
1.77
11.
459
1.23
1
0.89
80.
867
0.83
3
0.90
0.930.97
0.702.97
1.97
6.00
1.97
14.13
3.01
3.92
ppm (t1)050100150
0
50000
10000
15000
20000
25000
30000
35000179.
194
152.
667
146.
092
136.
433
135.
726
132.
969
131.
994
129.
113
126.
373
125.
877
124.
107
123.
823
118.
945
117.
184
77.0
00
37.2
9431
.795
29.3
9729
.237
29.1
8328
.926
28.7
38
27.4
86
22.6
0420
.734
14.5
0114
.047
N+
HN
HN
O
S
S 1k I-
200 MHz, CDCl3
N+
HN
HN
O
S
SI-
1k 50 MHz, CDCl3
SI-20
ppm (t1)1.02.03.04.05.06.07.08.0
0
10000
20000
30000
400007.
430
7.40
4
7.34
47.
319
7.29
17.
260
7.13
77.
089
2.42
6
2.052.08
1.98
3.00
300 MHz, CDCl3
2a
SHN
O
ppm (t1)50100150200
0
50000
10000
15000
166.
234
137.
689
129.
132
124.
438
119.
734
77.0
00
12.6
20
2a 75 MHz, CDCl3
SHN
O
SI-21
ppm (t1)0.01.02.03.04.05.06.07.08.0
0
10000
20000
30000
40000
50000
7.30
37.
275
7.26
07.
133
7.10
57.
028
2.41
22.
313
2.953.00
3.07
2.22
300 MHz, CDCl3
SHN
O
2b
ppm (t1)050100150
0
50000
10000
166.
346
135.
062
134.
278
129.
618
120.
120
77.0
00
20.8
37
12.6
03
166.
346
75 MHz, CDCl3 2b
SHN
O
SI-22
ppm (t1)2.03.04.05.06.07.08.09.0
0
10000
20000
300007.
941
7.59
8
7.31
5
7.26
0
2.46
61.94
0.96
1.52
3.00
200 MHz, CDCl3
HNS
O
CF3
CF3
2c
ppm (t1)050100150
0
50000
10000
166.
976
139.
060
133.
247
132.
800
132.
355
131.
909
128.
383
124.
768
121.
152
118.
928
118.
888
117.
527
117.
474
117.
424
77.0
00
12.6
92
75 MHz, CDCl3 HNS
O
CF3
CF3
2c
SI-23
ppm (t1)2.03.04.05.06.07.08.0
0
10000
20000
30000
40000
50000
8.23
18.
200
7.61
77.
586
7.34
97.
260
2.46
8
3.00
0.81
2.00
2.10
300 MHz, CDCl3
S
O
HN
NO2
2d
ppm (t1)50100150
0
50000
10000
166.
726
143.
439
143.
361
125.
309
118.
467
77.0
00
12.7
66
75 MHz, CDCl3
2d
S
O
HN
NO2
SI-24
ppm (t1)0.01.02.03.04.05.06.07.08.0
0
10000
20000
30000
40000
500007.
796
7.73
5
7.26
0
5.90
7
4.60
44.
584
2.38
9
3.00
2.01
1.04
3.21
SHN
O
CF3
CF3
300 MHz, CDCl3
2e
ppm (t1)050100150
0
50000
10000
168.
795
140.
585
132.
703
132.
260
131.
818
131.
375
128.
564
127.
632
127.
600
124.
948
121.
732
121.
684
121.
634
121.
584
121.
533
121.
335
117.
720
77.0
00
44.3
22
12.4
29
168.
795
75 MHz, CDCl3
SHN
O
CF3
CF3
2e
SI-25
ppm (t1)0.01.02.03.04.05.06.07.08.0
0
10000
20000
30000
400007.
432
7.40
37.
400
7.33
9
7.28
67.
260
7.13
17.
082
7.06
3
3.02
53.
001
2.97
62.
951
1.37
01.
346
1.32
1
3.00
2.04
2.03
4.21
300 MHz, CDCl3
2f
SHN
O
ppm (t1)050100150200
0
10000
20000
30000
40000
50000
165.
866
137.
725
129.
093
124.
355
119.
726
77.0
00
24.6
86
15.5
39
2f
SHN
O
75 MHz, CDCl3
SI-26
ppm (t1)0.01.02.03.04.05.06.07.08.0
0
10000
20000
30000
40000
50000
600007.32
37.
295
7.28
07.
145
7.11
77.
070
3.03
03.
006
2.98
12.
957
2.32
8
1.37
91.
355
1.33
0
1.78
3.03
2.03
3.13
3.00
300 MHz, CDCl3
2g
SHN
O
ppm (t1)050100150200
0
50000
10000
15000
20000
25000
30000
165.
834
135.
115
134.
182
120.
011
77.0
00
24.6
39
20.8
1515
.552
2g
SHN
O
75 MHz, CDCl3
SI-27
ppm (t1)1.02.03.04.05.06.07.08.0
0
10000
20000
30000
40000
50000
600007.
798
7.73
5
7.26
0
5.80
1
4.60
24.
582
2.99
82.
973
2.94
92.
924
1.34
11.
317
1.29
2
1.00
2.00
3.11
2.19
3.32
SHN
O
CF3
CF3
300 MHz, CDCl3
2h
ppm (t1)050100150
0
10000
20000
30000
40000
50000
60000
70000
80000168.
393
140.
642
132.
690
132.
248
131.
804
131.
360
128.
567
127.
607
127.
576
124.
954
121.
699
121.
648
121.
599
121.
548
121.
495
121.
340
117.
724
77.0
00
44.2
06
24.5
85
15.5
34
SHN
O
CF3
CF3
2h 75 MHz, CDCl3
SI-28
ppm (t1)1.02.03.04.05.06.07.0
0
10000
20000
30000
40000
500007.
260
5.26
0
4.04
24.
029
2.91
42.
889
2.86
42.
840
1.28
61.
262
1.23
71.
159
1.13
7
3.246.12
2.00
1.08
1.06
300 MHz, CDCl3 2i
SHN
O
ppm (t1)50100150
0
50000
10000
15000
20000
25000
30000
166.
141
77.0
00
43.5
64
24.1
46
22.7
7515
.662
75 MHz, CDCl3
2i
SHN
O
SI-29
ppm (t1)1.02.03.04.05.06.07.0
0
50000
10000
15000
20000
25000
30000
7.42
17.
401
7.32
97.
297
7.26
0
7.11
97.
089
7.00
3
2.98
62.
971
2.95
6
1.69
01.
675
1.66
01.
645
1.63
0
1.42
4
1.36
61.
261
0.89
30.
879
0.86
52.011.98
1.021.01
2.00
2.24
2.99
14.43
500 MHz, CDCl3 2j
HNS
O
ppm (t1)050100150
-15000
-10000
-50000
0
50000
10000
15000
20000
165.
903
137.
784
129.
113
124.
326
119.
643
77.0
00
31.8
75
30.3
5730
.284
29.5
1929
.505
29.2
8329
.125
28.7
7222
.664
14.0
97
2j HNS
O
DeptQ 135, 125 MHz, CDCl3
SI-30
ppm (t1)1.02.03.04.05.06.07.0
0
50000
10000
15000
7.30
37.
275
7.26
0
7.12
67.
099
6.97
6
2.98
12.
957
2.93
3
2.30
9
1.65
11.
388
1.35
91.
260
0.87
8
20000
1.95
3.00
2.31
14.32
3.00
2.241.950.73
300 MHz, CDCl3
2k HNS
O
ppm (t1)050100150
0
50000
10000
15000
165.
877
135.
158
134.
116
129.
588
119.
903
77.0
00
31.8
72
30.3
1129
.524
29.5
0029
.287
29.1
3228
.781
22.6
6620
.833
14.1
06
S
NH
O
2k
75 MHz, CDCl3
SI-31
ppm (t1)1.02.03.04.05.06.07.08.0
0
10000
20000
30000
40000
50000
7.26
0
3.57
13.
543
3.51
3
3.45
83.
429
3.39
92.
945
2.90
82.
871
2.83
4
1.72
91.
570
1.52
6
1.30
71.
270
1.23
4
4.16
2.01
4.203.89
3.18
S N
O
2l
ppm (t1)50100150
0
10000
20000
30000
40000
50000
167.
764
77.0
00
47.5
8447
.250
28.3
5427
.855
27.1
6426
.926
24.5
2315
.335
200 MHz, CDCl3
75 MHz, CDCl3
S N
O
2l
SI-32
ppm (t1)1.02.03.04.05.06.07.0
0
50000
10000
15000
20000
250007.26
0
3.36
7
2.91
82.
900
2.88
12.
863
1.29
31.
274
1.25
61.
154
5.90
2.00
4.00
3.15
ppm (t1)50100150
0
50000
10000
167.
200
77.0
00
41.8
81
24.4
66
15.3
4313
.371
S N
O
2m
400 MHz, CDCl3
100 MHz, CDCl3
S N
O
2m
SI-33
ppm (t1)1.02.03.04.05.06.07.0
0
10000
20000
30000
40000
50000
7.26
0
3.25
7
2.92
12.
896
2.87
22.
847
1.57
91.
293
1.26
81.
244
0.91
40.
889
0.86
5
4.21
1.99
4.36
2.98
6.20
S N
O
2n
ppm (t1)50100150
0
10000
20000
30000
40000167.
757
77.0
00
49.6
0249
.051
24.5
75
21.5
4021
.128
15.3
4011
.222
300 MHz, CDCl3
75 MHz, CDCl3
S N
O
2n
SI-34