phosphotungstic acid as a novel acidic catalyst for
TRANSCRIPT
Supporting Information
Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
Jyun-Siao Chen,a Arumugam Sankar,a Yi-Jyun Lin,a Po-Hsun Huang,a Chih-Hsiang Liao,b Shen-Shen Wu,c Hsin-Ru Wu,d Shun-Yuan Luoa*
a.Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan.
b.Taichung Municipal Feng Yuan Senior High School, Taichung 420, Taiwan
c.National Hsinchu Girls' Senior High School, Hsinchu 300, Taiwan.
d.Instrumentation Center, MOST, National Tsing Hua University, Hsinchu 300, Taiwan.
E-mail: [email protected]
Contents Page
NMR spectrum of important compounds 2-45
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2019
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
0.55
2.87
3.08
0.47
0.49
3.04
0.67
3.00
0.59
3.04
0.41
1.84
0.64
0.48
0.48
0.90
0.97
0.18
1.01
0.15
1.00
-0.0
08
1.59
32.
014
2.01
82.
029
2.03
22.
035
2.04
22.
087
2.09
52.
116
2.18
24.
070
4.07
64.
100
4.10
4
4.12
24.
122
4.13
14.
248
4.25
94.
280
4.29
05.
080
5.09
05.
106
5.11
65.
118
5.14
35.
168
5.44
65.
471
5.49
5
6.32
46.
333
7.26
0
Parameter Value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 16
Receiver Gain 36
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -800.3
Nucleus 1H
2
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.4
1520
.534
20.6
3320
.665
20.8
46
61.4
23
67.8
5769
.158
69.7
93
76.6
7476
.992
77.3
10
89.0
32
168.
707
169.
348
169.
610
170.
182
170.
588
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 216
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1441.7
Nucleus 13C
3
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
0.53
2.99
2.97
3.21
0.52
0.59
2.95
2.55
0.55
0.29
0.96
1.03
0.44
1.18
0.24
2.05
0.16
0.99
0.17
1.00
1.99
52.
005
2.02
22.
044
2.05
32.
124
2.15
92.
162
2.16
64.
054
4.07
14.
082
4.09
14.
099
4.10
74.
119
4.13
64.
322
4.32
64.
339
4.34
24.
356
4.35
9
5.33
05.
334
5.33
75.
418
5.42
15.
497
5.50
05.
684
5.70
5
6.37
46.
378
7.26
0
Parameter Value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 20
Receiver Gain 36
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -800.3
Nucleus 1H
4
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.2
5020
.352
20.5
1520
.589
60.9
8466
.199
67.1
0167
.175
68.4
99
76.6
6976
.989
77.3
08
89.4
22
168.
638
169.
579
169.
799
169.
849
170.
034
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 176
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1455.5
Nucleus 13C
5
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.22
3.14
2.92
3.13
3.13
1.14
1.38
1.16
1.19
2.04
1.00
1.99
92.
045
2.08
72.
163
2.17
1
4.03
74.
049
4.06
64.
071
4.09
84.
102
4.25
44.
266
4.28
44.
296
5.25
05.
332
5.33
45.
347
6.07
8
7.26
0
Parameter Value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 16
Receiver Gain 24
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -800.0
Nucleus 1H
6
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.2
5920
.286
20.3
2920
.382
20.4
74
61.7
6765
.195
68.0
1068
.447
70.2
46
76.6
7977
.000
77.3
19
90.2
48
167.
797
169.
266
169.
433
169.
672
170.
329
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 144
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1459.3
Nucleus 13C
7
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
2.92
3.19
2.79
2.90
2.96
0.96
1.43
1.21
0.94
0.90
1.03
1.00
2.00
72.
025
2.07
62.
098
3.40
74.
083
4.08
84.
113
4.11
94.
240
4.25
24.
271
4.88
84.
913
4.94
55.
065
5.44
85.
472
5.47
45.
497
7.26
0
Parameter Value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 16
Receiver Gain 30
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -800.0
Nucleus 1H
8
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.3
9920
.459
20.4
98
55.2
48
61.7
25
66.9
4168
.334
69.9
0270
.571
76.6
8177
.000
77.3
19
96.5
70
169.
377
169.
831
169.
897
170.
414
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 168
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1451.3
Nucleus 13C
9
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.04
3.22
2.91
9.09
3.07
0.20
1.14
1.13
0.23
0.24
0.15
0.22
1.95
0.26
0.28
0.33
1.25
0.18
1.00
-0.0
18-0
.016
-0.0
151.
854
1.87
91.
883
2.01
92.
044
2.04
72.
170
2.20
42.
208
2.21
52.
218
3.49
23.
513
3.52
23.
543
3.67
33.
701
3.72
83.
909
3.92
33.
936
3.95
13.
968
3.98
33.
998
4.01
34.
121
4.13
24.
151
4.16
34.
235
4.23
94.
252
4.33
14.
341
4.36
14.
371
4.95
25.
007
5.01
25.
014
5.01
65.
023
5.02
65.
030
5.03
25.
035
5.03
85.
040
5.04
15.
177
5.19
85.
219
5.23
45.
245
5.24
95.
259
5.26
45.
274
5.34
55.
358
5.37
05.
436
5.46
05.
486
5.69
65.
713
6.24
46.
253
7.26
0
Parameter Value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 28
Receiver Gain 26
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -800.0
Nucleus 1H
10
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.3
9020
.563
20.6
2620
.766
60.4
94
68.5
1669
.161
69.1
87
76.6
8277
.000
77.3
19
89.0
81
168.
920
169.
628
169.
666
170.
023
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 96
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1449.0
Nucleus 13C
11
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.02
2.77
0.52
1.02
0.55
2.83
2.70
3.08
0.62
0.61
2.77
0.50
2.95
2.95
0.37
1.37
1.37
1.21
4.35
1.01
1.30
1.26
1.19
0.37
1.24
0.30
0.17
1.21
1.18
0.21
1.00
-0.0
08-0
.007
1.23
51.
253
1.27
11.
604
1.96
52.
008
2.02
82.
040
2.04
82.
053
2.05
82.
062
2.09
52.
118
2.12
82.
152
2.15
92.
179
3.78
83.
812
3.83
63.
861
3.87
73.
895
3.98
03.
985
3.99
03.
994
4.00
64.
010
4.01
54.
019
4.05
94.
077
4.08
74.
105
4.12
34.
131
4.14
64.
158
4.17
44.
433
4.46
74.
475
4.48
74.
938
4.94
74.
964
4.97
24.
985
4.99
45.
011
5.02
05.
043
5.09
95.
118
5.12
55.
144
5.21
65.
239
5.29
75.
350
5.35
95.
434
5.45
95.
483
5.65
55.
676
6.24
46.
253
7.26
0
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 40
Receiver Gain 48
Relaxation Delay 1.0000
Acquisition Time 2.5559
Spectrometer Frequency 399.76
Spectral Width 6410.3
Lowest Frequency -799.4
Nucleus 1H
12
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.4
5620
.606
20.7
9820
.906
60.7
0161
.362
66.4
9069
.495
70.6
1170
.913
75.7
2576
.676
76.9
9577
.313
88.8
69
101.
132
168.
877
169.
073
169.
555
169.
874
170.
006
170.
080
170.
243
170.
284
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 248
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1445.9
Nucleus 13C
13
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
0.79
0.76
3.00
0.78
0.96
1.96
0.95
0.95
0.91
0.94
2.65
1.77
1.84
9
2.14
6
2.65
43.
413
3.44
93.
472
3.70
33.
727
3.74
23.
776
3.86
63.
889
4.24
14.
251
4.26
4
4.73
04.
740
5.49
5
7.24
27.
325
7.33
47.
340
7.34
87.
352
7.36
17.
375
7.45
67.
462
7.47
07.
481
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 8
Receiver Gain 30
Relaxation Delay 1.0000
Acquisition Time 2.5559
Spectrometer Frequency 399.76
Spectral Width 6410.3
Lowest Frequency -806.6
Nucleus 1H
14
0102030405060708090100110120130140150160170180190200f1 (ppm)
55.8
25
62.8
02
69.1
8371
.832
73.0
5376
.993
77.3
1177
.629
81.1
77
100.
048
102.
194
126.
578
128.
613
129.
548
137.
261
ParametersParameter Value
1 Origin Varian2 Spectrometer vnmrs3 Solvent cdcl34 Temperature 20.05 Pulse Sequence s2pul6 Experiment 1D7 Number of Scans 10728 Receiver Gain 309 Relaxation Delay 2.000010 Acquisition Time 1.310711 Spectrometer Frequency 100.5312 Spectral Width 25000.013 Lowest Frequency -1413.914 Nucleus 13C
15
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
2.89
1.01
1.07
1.07
1.05
1.03
1.02
1.05
0.96
1.00
1.88
1.99
2.77
1.95
1.95
1.87
-0.0
16
1.69
4
2.28
83.
309
3.52
93.
552
3.57
53.
623
3.63
53.
642
3.64
73.
760
3.78
63.
811
4.24
84.
274
4.29
94.
342
4.35
54.
369
4.38
14.
552
4.57
7
5.52
95.
585
5.61
27.
037
7.05
67.
240
7.24
77.
263
7.26
77.
329
7.33
17.
336
7.34
57.
434
7.44
07.
446
7.45
27.
455
7.46
47.
703
7.70
87.
716
7.72
17.
724
7.81
47.
865
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent cdcl3
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 20
8 Receiver Gain 30
9 Relaxation Delay 1.0000
10 Acquisition Time 2.5559
11 Spectrometer Frequency 399.76
12 Spectral Width 6410.3
13 Lowest Frequency -806.6
14 Nucleus 1H
16
0102030405060708090100110120130140150160170180190200f1 (ppm)
18.5
53
53.0
49
65.9
7967
.137
67.6
88
74.1
2274
.440
74.7
5879
.314
81.8
78
99.3
43
120.
757
121.
261
123.
700
125.
206
125.
789
126.
784
127.
115
129.
061
130.
731
131.
627
134.
295
135.
859
165.
006
165.
665
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent D2O
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 1024
8 Receiver Gain 30
9 Relaxation Delay 2.0000
10 Acquisition Time 1.3107
11 Spectrometer Frequency 100.53
12 Spectral Width 25000.0
13 Lowest Frequency -1443.0
14 Nucleus 13C
17
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
5.91
9.21
1.25
1.15
1.03
2.26
1.17
1.14
1.12
1.00
2.87
1.95
0.17
40.
187
0.96
40.
971
3.17
63.
262
3.28
13.
284
3.30
43.
331
3.34
13.
480
3.50
33.
521
3.54
03.
563
3.71
33.
739
3.76
44.
245
4.25
74.
271
4.58
04.
599
5.50
0
7.26
07.
370
7.37
57.
383
7.38
77.
392
7.39
37.
396
7.48
07.
485
7.49
47.
505
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent cdcl3
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 36
8 Receiver Gain 30
9 Relaxation Delay 1.0000
10 Acquisition Time 2.5559
11 Spectrometer Frequency 399.76
12 Spectral Width 6410.3
13 Lowest Frequency -798.6
14 Nucleus 1H
18
-100102030405060708090100110120130140150160170180190200f1 (ppm)
-5.2
53-4
.431
17.8
18
25.4
74
66.1
4968
.397
68.8
7471
.501
76.6
8277
.000
77.3
1880
.650
97.3
97
101.
834
126.
247
128.
268
129.
243
136.
808
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent cdcl3
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 80
8 Receiver Gain 30
9 Relaxation Delay 2.0000
10 Acquisition Time 1.3107
11 Spectrometer Frequency 100.53
12 Spectral Width 25000.0
13 Lowest Frequency -1452.2
14 Nucleus 13C
19
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.00
0.79
0.80
1.06
2.01
0.96
0.87
0.97
0.94
0.93
1.86
2.91
3.95
-0.0
07
1.59
9
2.36
2
2.65
82.
803
3.40
93.
430
3.43
33.
454
3.49
33.
499
3.51
13.
516
4.36
14.
372
4.38
74.
398
4.56
14.
585
5.52
7
7.14
47.
164
7.26
07.
356
7.36
17.
369
7.37
37.
383
7.42
27.
427
7.43
17.
443
7.44
77.
452
7.46
17.
466
7.47
47.
485
Parameter value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 80
Receiver Gain 39
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -801.5
Nucleus 1H
20
0102030405060708090100110120130140150160170180190200f1 (ppm)
21.1
26
68.4
4870
.301
72.3
9974
.346
76.6
7376
.991
77.3
0980
.052
88.5
01
101.
758
126.
248
127.
365
128.
292
129.
248
129.
782
133.
471
136.
787
138.
633
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 1204
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1450.9
Nucleus 13C
21
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.00
1.78
0.96
1.03
0.93
0.95
0.95
0.92
0.93
0.94
1.91
4.89
1.99
2.24
0
2.54
7
3.40
43.
479
3.50
23.
524
3.55
03.
881
3.91
24.
061
4.06
94.
236
4.26
74.
316
4.33
8
5.37
5
6.98
37.
003
7.14
17.
250
7.26
07.
448
7.46
8
Parameter value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 104
Receiver Gain 30
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -846.9
Nucleus 1H
22
0102030405060708090100110120130140150160170180190200f1 (ppm)
21.2
22
68.6
0069
.232
69.9
1173
.774
75.2
8776
.673
76.9
9177
.309
86.9
34
101.
327
126.
532
128.
144
129.
299
129.
673
134.
228
137.
538
138.
472
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 732
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1446.3
Nucleus 13C
23
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.00
3.19
0.81
3.09
4.40
2.21
1.08
1.06
1.00
4.96
-0.0
03
0.89
2
1.25
11.
437
1.63
71.
905
1.98
62.
079
2.09
42.
144
2.82
53.
395
3.72
03.
736
3.74
43.
763
3.77
33.
792
3.81
9
4.50
84.
559
4.58
94.
610
4.64
04.
849
4.85
84.
875
4.88
44.
904
4.91
35.
127
5.27
65.
299
5.32
4
7.26
07.
289
7.30
57.
311
7.33
77.
344
7.35
0
Parameter value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 28
Receiver Gain 39
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -800.3
Nucleus 1H
24
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.6
4020
.775
55.0
68
69.1
7969
.962
70.0
5870
.708
72.9
2173
.500
76.6
8177
.000
77.3
18
96.6
36
127.
496
127.
599
128.
269
137.
658
170.
250
171.
344
176.
837
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 120
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1454.3
Nucleus 13C
25
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.16
2.92
3.11
1.19
1.18
2.08
2.21
0.98
1.02
1.00
2.04
7.45
-0.0
10-0
.004
-0.0
020.
006
0.91
60.
934
0.95
30.
977
0.99
41.
065
1.24
01.
258
1.27
6
1.65
62.
009
2.04
52.
057
2.06
62.
089
2.16
42.
227
2.31
93.
540
3.55
23.
564
3.69
63.
719
3.78
83.
799
3.80
33.
815
4.53
24.
561
4.57
44.
604
4.61
84.
643
4.87
84.
902
4.90
34.
926
5.03
55.
058
5.08
25.
299
7.06
57.
086
7.26
07.
287
7.29
27.
303
7.31
27.
321
7.33
87.
347
7.35
27.
368
7.37
37.
384
7.38
9
Parameter value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 24
Receiver Gain 39
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -800.0
Nucleus 1H
26
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.7
8021
.080
69.8
6869
.934
70.0
1273
.653
76.6
8177
.000
77.3
1878
.441
85.7
58
127.
641
127.
756
127.
980
128.
365
129.
598
133.
351
137.
587
138.
352
169.
519
171.
155
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 80
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1418.8
Nucleus 13C
27
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.04
0.81
2.38
1.18
1.16
1.70
1.79
1.03
2.18
1.12
0.82
1.96
12.9
12.
212.
13
2.15
32.
312
2.33
42.
552
3.43
33.
455
3.46
93.
478
3.50
53.
527
3.64
43.
757
3.77
03.
782
4.56
44.
575
4.61
54.
639
4.72
74.
753
4.76
54.
793
4.89
54.
910
4.92
44.
935
7.04
27.
062
7.11
17.
260
7.29
87.
306
7.31
47.
319
7.32
37.
331
7.33
67.
344
7.35
07.
353
7.36
67.
413
7.42
97.
433
7.45
27.
472
Parameter value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 64
Receiver Gain 39
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -799.6
Nucleus 1H
28
0102030405060708090100110120130140150160170180190200f1 (ppm)
21.0
90
70.3
3071
.638
73.6
0175
.310
75.4
5776
.682
77.0
0077
.318
77.9
8980
.386
86.1
2687
.899
127.
665
127.
915
128.
233
128.
369
128.
399
128.
565
129.
634
129.
682
132.
571
137.
727
137.
876
137.
950
138.
105
138.
165
138.
390
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 60
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1446.7
Nucleus 13C
29
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.14
2.97
3.05
0.91
1.11
1.96
1.00
1.79
1.02
1.02
1.00
2.12
4.79
2.09
2.07
42.
082
2.31
32.
611
2.61
32.
617
2.61
92.
620
3.69
63.
709
3.72
13.
774
3.78
43.
796
4.16
34.
171
4.55
64.
568
4.94
24.
950
4.96
74.
974
5.24
25.
267
5.29
1
7.06
07.
080
7.30
07.
318
7.33
47.
350
7.40
17.
421
Parameter value
Origin Varian
Spectrometer mercury
Solvent cdcl3
Temperature 25.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 72
Receiver Gain 39
Relaxation Delay 1.0000
Acquisition Time 2.5575
Spectrometer Frequency 400.43
Spectral Width 6406.1
Lowest Frequency -800.7
Nucleus 1H
30
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.8
9721
.159
29.6
94
67.6
1568
.269
69.5
0773
.794
74.5
0976
.682
76.9
0077
.000
77.3
18
86.4
61
127.
750
127.
879
128.
320
128.
467
129.
643
133.
271
137.
490
138.
315
155.
200
164.
778
169.
455
170.
182
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 448
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1443.0
Nucleus 13C
31
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
1.64
3.00
1.13
0.83
1.11
1.02
1.73
0.64
0.78
1.20
3.08
0.87
1.16
0.74
8.39
2.15
52.
165
3.27
53.
293
3.30
13.
497
3.51
93.
537
3.65
63.
670
3.71
63.
723
3.74
14.
065
4.07
3
4.55
24.
558
4.56
54.
573
4.77
3
5.29
15.
299
5.32
35.
325
5.34
9
7.27
47.
290
7.30
67.
311
7.32
67.
339
7.34
27.
361
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 40
Receiver Gain 30
Relaxation Delay 1.0000
Acquisition Time 2.5559
Spectrometer Frequency 399.76
Spectral Width 6410.3
Lowest Frequency -799.4
Nucleus 1H
32
0102030405060708090100110120130140150160170180190200f1 (ppm)
20.9
53
61.3
76
64.5
0369
.378
70.0
1370
.261
70.4
1873
.498
73.6
0173
.646
74.5
1276
.682
77.0
0077
.318
91.8
41
95.8
42
127.
942
127.
976
128.
455
128.
485
137.
131
137.
300
171.
784
171.
906
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 208
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1443.1
Nucleus 13C
33
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
2.99
3.00
1.09
4.17
1.25
2.26
2.16
2.07
2.14
4.75
2.23
2.06
-0.0
02
1.90
8
2.29
2
2.91
23.
756
3.78
93.
811
3.83
03.
841
3.85
53.
867
4.23
94.
265
4.29
14.
561
4.59
14.
608
4.63
7
5.62
35.
645
5.64
95.
652
5.67
15.
679
7.01
57.
035
7.26
07.
277
7.29
77.
327
7.33
57.
344
7.35
37.
371
7.73
57.
743
7.74
97.
757
7.85
37.
861
7.86
67.
874
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 28
Receiver Gain 58
Relaxation Delay 1.0000
Acquisition Time 2.5559
Spectrometer Frequency 399.76
Spectral Width 6410.3
Lowest Frequency -799.4
Nucleus 1H
34
0102030405060708090100110120130140150160170180190200f1 (ppm)
13.9
02
20.5
3420
.646
21.1
26
52.5
8453
.585
70.1
7971
.027
73.6
8774
.281
76.6
7676
.994
77.3
1278
.257
83.1
79
123.
539
123.
640
127.
506
127.
695
127.
790
128.
419
129.
603
131.
164
131.
588
133.
454
134.
143
134.
337
137.
681
138.
348
167.
245
167.
824
171.
072
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 240
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1445.5
Nucleus 13C
35
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.15
2.85
9.02
3.01
3.03
3.09
1.08
1.00
2.46
1.19
1.06
1.06
2.05
1.00
1.07
1.03
1.01
1.09
2.02
3.07
3.01
0.93
1.04
2.01
2.02
0.07
00.
073
0.87
51.
861
2.14
93.
246
3.26
53.
271
3.28
63.
291
3.29
53.
329
3.61
23.
623
3.69
53.
718
3.74
13.
766
3.90
53.
928
3.95
24.
182
4.20
34.
208
4.22
94.
250
4.28
04.
361
4.36
94.
386
4.39
94.
457
4.47
74.
876
4.89
94.
902
4.92
55.
490
5.51
15.
517
5.81
95.
842
5.84
45.
868
7.19
17.
207
7.21
17.
260
7.26
67.
280
7.28
47.
299
7.30
37.
313
7.31
77.
353
7.35
97.
367
7.37
17.
376
7.38
07.
437
7.44
27.
451
7.46
27.
695
7.70
27.
708
7.71
67.
822
7.83
07.
836
7.84
3
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent cdcl3
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 88
8 Receiver Gain 30
9 Relaxation Delay 1.0000
10 Acquisition Time 2.5559
11 Spectrometer Frequency 399.76
12 Spectral Width 6410.3
13 Lowest Frequency -799.0
14 Nucleus 1H
36
-100102030405060708090100110120130140150160170180190200f1 (ppm)
-5.3
86-4
.580
17.7
6220
.371
21.1
4225
.379
55.4
6865
.795
66.2
7467
.258
68.5
2469
.514
72.4
3172
.683
74.1
8574
.583
76.6
8277
.000
77.3
1978
.840
96.7
2598
.156
101.
503
123.
435
126.
095
127.
257
127.
395
128.
125
129.
096
131.
206
134.
247
136.
628
137.
787
169.
232
170.
053
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent cdcl3
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 2016
8 Receiver Gain 30
9 Relaxation Delay 2.0000
10 Acquisition Time 1.3107
11 Spectrometer Frequency 100.53
12 Spectral Width 25000.0
13 Lowest Frequency -1441.8
14 Nucleus 13C
37
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
2.412.83
9.01
2.88
4.60
2.292.371.02
3.341.101.05
1.151.17
1.101.07
1.23
1.983.102.854.672.262.932.95
3.29
03.
314
3.33
23.
349
3.36
93.
393
3.42
13.
441
3.46
53.
697
3.70
93.
723
3.73
53.
746
3.75
93.
770
3.79
53.
818
3.83
93.
863
3.88
84.
041
4.06
64.
316
4.34
34.
367
4.39
34.
413
4.47
14.
489
4.59
54.
622
4.85
44.
882
4.99
25.
020
5.52
45.
545
5.57
05.
847
5.87
15.
896
7.02
57.
040
7.24
07.
257
7.28
07.
388
7.39
97.
459
7.48
17.
486
7.49
57.
503
7.51
17.
585
7.59
27.
598
7.60
57.
727
7.73
47.
739
7.74
87.
755
7.79
17.
815
7.83
77.
848
7.86
3
ParametersParameter Value
1 Origin Varian2 Spectrometer vnmrs3 Solvent cdcl34 Temperature 20.05 Pulse Sequence s2pul6 Experiment 1D7 Number of Scans 928 Receiver Gain 309 Relaxation Delay 1.000010 Acquisition Time 2.555911 Spectrometer Frequency 399.7612 Spectral Width 6410.313 Lowest Frequency -791.214 Nucleus 1H
38
-100102030405060708090100110120130140150160170180190200f1 (ppm)
-5.397
-4.206
17.891
20.571
25.623
30.913
55.226
66.240
68.048
68.530
68.649
69.948
74.245
74.850
75.377
76.877
77.195
77.514
77.653
79.186
82.612
97.121
98.178
101.664
123.510
125.965
126.061
126.100
126.285
126.734
127.653
127.711
127.827
127.975
128.164
128.282
128.341
129.204
133.038
133.278
134.168
135.531
136.948
137.626
170.217
ParametersParameter Value
1 Origin Varian2 Spectrometer vnmrs3 Solvent cdcl34 Temperature 20.05 Pulse Sequence s2pul6 Experiment 1D7 Number of Scans 13608 Receiver Gain 309 Relaxation Delay 2.000010 Acquisition Time 1.310711 Spectrometer Frequency 100.5312 Spectral Width 25000.013 Lowest Frequency -1443.114 Nucleus 13C
39
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.07
2.83
9.70
3.00
2.97
1.08
2.43
2.11
2.36
1.04
1.92
2.14
1.03
1.06
1.08
0.83
1.09
2.12
3.06
1.98
3.55
2.39
2.12
2.20
0.01
00.
074
0.86
5
1.56
7
1.89
01.
971
3.19
63.
242
3.45
33.
706
3.71
73.
731
3.74
23.
774
3.83
13.
986
4.26
34.
273
4.35
24.
365
4.37
34.
378
4.39
94.
525
4.88
84.
914
4.93
2
5.48
85.
525
5.54
25.
821
5.84
75.
870
6.94
16.
952
6.95
86.
964
7.21
17.
213
7.21
87.
224
7.22
97.
260
7.26
47.
354
7.35
97.
367
7.37
17.
448
7.45
37.
462
7.47
17.
632
7.63
97.
645
7.65
37.
760
Parameter value
Origin Varian
Spectrometer mercury
Solvent CDCl3
Temperature 29.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 80
Receiver Gain 20
Relaxation Delay 0.0000
Acquisition Time 2.8000
Spectrometer Frequency 400.44
Spectral Width 6006.0
Lowest Frequency -476.4
Nucleus 1H
40
0102030405060708090100110120130140150160170180190200f1 (ppm)
17.7
4120
.535
20.8
3425
.498
55.1
98
66.2
3166
.312
67.8
4768
.602
69.7
8573
.580
74.0
7274
.379
76.0
5776
.675
76.9
9377
.311
79.1
18
97.0
2398
.190
101.
653
123.
523
126.
204
127.
529
127.
839
128.
231
128.
307
129.
159
134.
202
136.
839
137.
124
169.
711
170.
193
Parameter value
Origin Varian
Spectrometer vnmrs
Solvent cdcl3
Temperature 20.0
Pulse Sequence s2pul
Experiment 1D
Number of Scans 612
Receiver Gain 30
Relaxation Delay 2.0000
Acquisition Time 1.3107
Spectrometer Frequency 100.53
Spectral Width 25000.0
Lowest Frequency -1443.2
Nucleus 13C
41
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
2.94
3.01
9.05
3.00
1.07
1.09
1.08
1.09
1.00
3.10
1.04
1.04
1.07
1.00
2.08
1.06
1.09
6.02
4.02
2.01
2.00
0.06
00.
071
0.84
8
1.88
13.
179
3.19
83.
203
3.22
23.
476
3.50
03.
557
3.58
03.
693
3.71
83.
737
3.76
04.
052
4.06
34.
229
4.24
34.
369
4.39
14.
395
4.41
64.
517
4.53
6
5.48
55.
522
5.55
35.
574
5.87
35.
897
5.92
27.
260
7.33
97.
344
7.35
57.
373
7.38
67.
432
7.43
77.
447
7.45
67.
473
7.47
87.
666
7.67
37.
679
7.68
77.
842
7.85
07.
855
7.86
3
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent cdcl3
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 52
8 Receiver Gain 18
9 Relaxation Delay 1.0000
10 Acquisition Time 2.5559
11 Spectrometer Frequency 399.76
12 Spectral Width 6410.3
13 Lowest Frequency -797.8
14 Nucleus 1H
42
-100102030405060708090100110120130140150160170180190200f1 (ppm)
-5.3
24-4
.543
17.6
5520
.460
25.3
61
55.3
74
66.0
4066
.340
67.4
1168
.228
68.4
5969
.679
76.6
8177
.000
77.3
1878
.865
79.0
1280
.614
97.6
8099
.821
101.
080
101.
478
123.
359
125.
868
126.
161
128.
014
128.
111
129.
037
131.
249
134.
084
136.
779
136.
930
170.
010
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent cdcl3
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 440
8 Receiver Gain 30
9 Relaxation Delay 2.0000
10 Acquisition Time 1.3107
11 Spectrometer Frequency 100.53
12 Spectral Width 25000.0
13 Lowest Frequency -1454.3
14 Nucleus 13C
43
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.03
3.04
9.06
3.13
3.10
3.08
3.01
1.36
1.03
1.24
1.25
1.21
1.21
1.17
1.21
1.18
1.17
1.15
2.73
1.04
1.00
3.05
2.30
0.13
10.
146
0.91
3
1.95
71.
966
1.97
52.
054
3.28
93.
308
3.31
33.
332
3.58
63.
610
3.63
53.
658
3.77
03.
848
3.85
44.
058
4.06
84.
239
4.58
44.
604
4.72
64.
746
5.06
15.
133
5.15
7
5.52
1
7.26
07.
315
7.31
87.
326
7.33
27.
423
7.43
27.
442
7.44
7
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent cdcl3
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 24
8 Receiver Gain 30
9 Relaxation Delay 1.0000
10 Acquisition Time 2.5559
11 Spectrometer Frequency 399.76
12 Spectral Width 6410.3
13 Lowest Frequency -806.6
14 Nucleus 1H
44
-100102030405060708090100110120130140150160170180190200f1 (ppm)
-5.3
35-4
.466
17.7
5220
.460
20.4
9220
.563
25.3
91
61.4
3466
.356
67.8
6868
.346
68.3
8271
.397
71.6
4572
.694
76.6
8177
.000
77.3
1879
.123
79.4
18
97.5
2010
0.95
010
1.21
5
125.
875
128.
079
129.
100
136.
919
169.
194
169.
299
170.
199
170.
539
Parameter Value
1 Origin Varian
2 Spectrometer vnmrs
3 Solvent cdcl3
4 Temperature 20.0
5 Pulse Sequence s2pul
6 Experiment 1D
7 Number of Scans 2408
8 Receiver Gain 30
9 Relaxation Delay 2.0000
10 Acquisition Time 1.3107
11 Spectrometer Frequency 100.53
12 Spectral Width 25000.0
13 Lowest Frequency -1451.3
14 Nucleus 13C
45