Supporting Information
Table of Contents:
1
H,
13C and bidimensional NMR spectra S2 – S48
-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
f1 (ppm)
3.25
5.99
3.98
4.17
4.00
2.40
6.66
2.09
5.81 2.41
2.49
2.87
3.35
4.46
7.28
7.30
7.39
7.41
7.42
7.44
7.57
7.59
7.73
7.75
7.78
7.80
7.82
7.84
7.86 1
H NMR, 300 MHz, CDCl
3, 330K
DCE [Ag(PcL
2)
]
hexanes
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
f1 (ppm)
21.73
21.85
57.03
125.48
127.80
128.32
130.19
130.56
141.11
144.98
145.37
[Ag(PcL
2) ]
13
C NMR, 100 MHz, CDCl
3, 300K DCE
hexanes
21.6 21.8 22.0
f1 (ppm)
21.73
21.85
124 126 128 130 132 134 136 138 140 142 144 146
f1 (ppm)
125.48
127.80
128.32
130.19
130.56
141.11
144.98
145.37
1 2
3 4
5 6
7 8
f2 (ppm)
10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160
f1 ( p p m )
[Ag(PcL
2) ]
HSQC, 400 MHz, CDCl
3, 330K
-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
f1 (ppm)
2.11
2.04
3.99
5.95
3.95
1.98
2.59
17.83
1.54 3.01
3.23
3.33
3.80
3.94
6.86
6.88
7.16
7.17
7.28
7.31
7.32
7.35
7.36
7.51
7.53 1
H NMR, 400 MHz, CDCl
3[Ag(PcL
3)
]
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
f1 (ppm)
49.9
51.4
52.0
58.7
61.8
120.5127.9
128.6
129.3
129.4
130.0
130.8
137.3
137.9
159.1
13
C NMR, 100 MHz, CDCl
3128.0
128.5 129.0 129.5 130.0 130.5 131.0
f1 (ppm)
127.9
128.6
129.3
129.4
130.0
130.8
[Ag(PcL
3)
]
-6.5 -6.0 -5.5 -5.0 -4.5 -4.0 -3.5 -3.0 -2.5 -2.0 -1.5 -1.0 -0.5 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0
f1 (ppm)
-0.95
11
B NMR, 128.4 MHz, CD
2Cl
2[Ag(PcL
3)
]
-156.0 -155.5
-155.0 -154.5
-154.0 -153.5
-153.0 -152.5
-152.0 -151.5
-151.0 -150.5
-150.0 -149.5
-149.0 -148.5
-148.0 -147.5
-147.0 -146.5
-146.0
f1 (ppm)
-151.50
-151.45
-151.75 -151.65
-151.55 -151.45
-151.35 -151.25
f1 (ppm)
-151.50
-151.45
19
F NMR, 376.5 MHz, DMSO
[Ag(PcL
3)
]
-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
ppm
3.12
3.17
1.00
1.01
1.05
2.19
2.10
1.77
2.39
1.13
2.16
1.00 1.94
2.02
6.43
6.52
6.54
6.57
6.66
6.68
6.89
6.91
6.98
6.99
7.00
7.02
7.107.13
7.24
7.27
7.30
7.48
7.51
7.63
7.65
10.05
10.08
6.3 6.4 6.5 6.6 6.7 6.8 6.9 7.0 7.1 7.2 7.3 7.4 7.5 7.6 7.7
ppm
1.00
1.01
1.05
2.19
2.10
1.77
2.39
1.13
2.16 6.43
6.52
6.54
6.57
6.66
6.68
6.89
6.91
6.98
6.99
7.00
7.02
7.10
7.13
7.24
7.27
7.30
7.48
7.51
7.63
7.65
3a
1
H NMR, 300 MHz, C
6D
6grease DCM
O
N H
CH
3O
CH
30 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
20.94
27.33
81.19
100.36
113.83
116.60
119.48
124.46
124.92
125.60
126.59
128.06
129.08
129.13
131.66
132.55
132.64
134.51
138.42
148.35
151.20
200.40
3a
13
C NMR, 75 MHz, C
6D
6126.5 127.0
127.5 128.0
128.5 129.0
ppm
126.59
128.06
129.08
129.13
grease
O
N H
CH
3O
CH
32 3
4 5
6 7
8 9
10
ppm
2
3
4
5
6
7
8
9
10
p p m
3a
O
N H
CH
3O
CH
3COSY, 300 MHz, C
6D
6,rt
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
ppm
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
10.0
10.5
p p m
3a
O
N H
CH
3O
CH
3COSY, 300 MHz, C
6D
6,rt
1 2
3 4
5 6
7 8
9 10
ppm
10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210
p p m
3a
O
N H
CH
3O
CH
3HSQC, 300 MHz, C
6D
6,rt
6.1 6.2 6.3 6.4 6.5 6.6 6.7 6.8 6.9 7.0 7.1 7.2 7.3 7.4 7.5 7.6 7.7 7.8 7.9
ppm
80
85
90
95
100
105
110
115
120
125
130
135
p p m
3a HSQC, 300 MHz, C
6D
6,rt
O
N H
CH
3O
CH
3-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
3.34
3.00
1.03
1.03
1.03
2.15
1.14
2.31
2.37
3.79
2.04
2.01 2.00
2.16
4.49
4.52
6.41
6.46
6.49
6.51
6.53
6.81
6.84
6.89
6.92
7.00
7.00
7.03
7.05
7.16
7.17
7.19
7.20
7.59
7.61
7.83
7.86
1
H NMR, 300 MHz, C
6D
63b
6.4 6.5 6.6 6.7 6.8 6.9 7.0 7.1 7.2 7.3 7.4 7.5 7.6 7.7 7.8
ppm
1.03
1.03
2.15
1.14
2.31
2.37
3.79
2.04
2.01 6.41
6.46
6.49
6.51
6.53
6.81
6.846.89
6.92
7.00
7.00
7.03
7.05
7.16
7.17
7.19
7.20
7.59
7.61
7.83
7.86
traces of diispropyl ether
traces of diispropyl ether O
N H
CH
3O
CH
3-20 -10
0 10 20
30 40
50 60
70 80 90
100 110
120 130
140 150
160 170 180
190 200
210 220
ppm
20.91
25.60
81.03
99.38
113.34
124.25
125.62
125.67
126.42
129.23
129.36
129.45
130.49
131.53
132.36
138.94
148.61
151.55
194.58
3b
13
C NMR, 75 MHz, C
6D
6123 124
125 126
127 128
129 130
131 132
ppm
124.25
125.62
125.67
126.42
129.23
129.36
129.45
130.49
131.53
132.36
O
N H
CH
3O
CH
3-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
3.30
1.08
2.04
1.01
1.00
1.01
2.11
2.33
1.15
2.03
2.10 2.01
4.43
4.46
6.13
6.16
6.23
6.26
6.39
6.75
6.78
6.92
6.94
6.97
6.98
7.00
7.00
7.04
7.17
7.17
7.19
7.20
7.52
7.55
7.93
7.96
1
H NMR, 300 MHz, C
6D
63c
6.0 6.2 6.4 6.6 6.8 7.0 7.2 7.4 7.6 7.8 8.0
ppm
2.04
1.01
1.00
1.01
2.11
2.33
1.15
2.03
2.10 6.13
6.16
6.23
6.26
6.39
6.75
6.78
6.92
6.94
6.97
6.98
7.00
7.00
7.04
7.17
7.17
7.19
7.20
7.52
7.55
7.93
7.96
O
N H
CH
3N
+O
O
-grease
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
20.76
80.45
99.20
112.82
124.21
125.37
125.56
126.38
126.73
129.11
129.45
131.21
131.86
139.06
140.33
149.51
151.17
13
C NMR, 75 MHz, C
6D
63c
122 123
124 125
126 127
128 129
130 131
132 133
ppm
124.21
125.37
125.56
126.38
126.73
129.11
129.45
131.21
131.86
O
N H
CH
3N
+O
O
--0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
ppm
3.48
0.98
1.00
1.02
3.72
1.27
1.05
1.01
1.05
1.99
0.97
0.95 2.03
6.23
6.24
6.26
6.26
6.266.28
6.29
6.37
6.42
6.44
6.91
6.91
6.93
6.93
6.94
6.94
6.95
6.98
7.00
7.00
7.01
7.01
7.02
7.03
7.03
7.03
7.09
7.09
7.11
7.11
7.12
7.14
7.31
7.32
7.34
7.34
7.55
7.57
7.90
7.91
7.93
7.93
8.60
8.63
1
H NMR, 300 MHz, C
6D
63d
O
N H
CH
3N
+O
O
-grease
DCM
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
20.78
80.68
100.09
115.36
117.39
124.50
124.72
125.31
126.49
126.67
126.93
129.00
129.40
131.10
132.01
133.84
135.16
138.67
142.19
150.69
grease
3d
123 124 125 126 127 128 129 130 131 132 133 134 135 136
ppm
124.50
124.72
125.31
126.49
126.67
126.93
129.00
129.40
131.10
132.01
133.84
135.16
13
C NMR, 75 MHz, C
6D
6O
N H
CH
3N
+O
O
--0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
3.15
0.99
1.00
1.94
1.08
5.75
0.97
1.00
1.86 2.02
4.87
4.87
4.90
4.91
6.35
6.52
6.55
6.75
6.75
6.77
6.78
6.78
6.79
6.81
6.81
6.87
6.90
6.93
6.95
6.95
6.97
7.00
7.10
7.10
7.12
7.27
7.27
7.29
7.30
7.32
7.33
7.56
7.58
3e
1
H NMR, 300 MHz, C
6D
6O
N H
F
CH
36.5 7.0
7.5
ppm
1.00
1.94
1.08
5.75
0.97
1.00
1.86 6.35
6.52
6.55
6.75
6.75
6.77
6.78
6.78
6.79
6.81
6.81
6.87
6.90
6.93
6.95
6.95
6.97
7.00
7.10
7.10
7.12
7.27
7.27
7.29
7.30
7.32
7.33
7.56
7.58
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
20.93
81.79
81.82
99.66
114.96
115.03
115.06
115.21
119.26
119.35
124.32
124.58
124.63
125.40
125.63
126.49
127.89
129.11
129.15
131.52
132.48
133.38
133.53
138.60
150.64
151.23
153.81
13
C NMR, 75 MHz, C
6D
63e
115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134
ppm
114.96115.03
115.06
115.21
119.26
119.35
124.32
124.58
124.63
125.40
125.63
126.49
127.89
129.11
129.15
131.52
132.48
133.38
133.53
O
N H
F
CH
3-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
ppm
3.08
3.24
1.00
1.11
3.02
2.20
2.05
2.01
1.05
2.00
0.99 1.91
3.17
6.32
6.48
6.49
6.51
6.51
6.53
6.54
6.62
6.65
6.93
6.94
6.96
6.99
7.08
7.08
7.10
7.22
7.22
7.25
7.27
7.45
7.48
7.57
7.60
10.02
10.04
3f
1
H NMR, 300 MHz, C
6D
6O
N H
O CH
3O
CH
36.4 6.6
6.8 7.0
7.2 7.4
7.6
ppm
1.00
1.11
3.02
2.20
2.05
2.01
1.05
2.00 6.32
6.486.49
6.51
6.51
6.53
6.54
6.62
6.65
6.93
6.94
6.96
6.99
7.08
7.08
7.10
7.22
7.22
7.25
7.27
7.45
7.48
7.57
7.60
grease
DCM
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
27.09
54.35
81.19
99.30
113.68
113.72
116.43
119.46
124.13
124.69
126.20
126.92
127.83
128.95
131.76
132.35
134.29
148.28
151.01
160.32
200.16
3f
13
C NMR, 75 MHz, C
6D
6134 132 130 128 126 124 122 120 118 116 114 112 110
ppm
113.68
113.72
116.43
119.46
124.13
124.69
126.20
126.92
127.83
128.95
131.76
132.35
134.29
O
N H
O CH
3O
CH
3grease
-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
3.38
3.33
1.07
1.05
1.16
1.15
2.52
2.15
6.73
1.10
1.00
1.06 1.84
3.10
6.34
6.36
6.39
6.42
6.44
6.57
6.59
6.68
6.69
6.71
6.73
6.74
6.85
6.87
6.89
6.89
6.90
6.91
6.98
6.99
7.03
7.057.08
7.16
7.16
7.19
7.19
7.36
7.39
7.84
7.84
7.86
7.87
10.02
10.04 1
H NMR, 300 MHz, C
6D
63g
O
N H
O
O
CH
3CH
30 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
27.15
54.54
80.91
106.49
111.03
113.84
116.30
119.32
120.31
124.20
124.57
124.71
126.56
128.22
128.84
128.88
129.14
131.90
132.27
134.31
147.96
148.39
157.69
200.16
104 106 108 110 112 114 116 118 120 122 124 126 128 130 132 134
ppm
106.49
111.03
113.84
116.30
119.32
120.31
124.20
124.57
124.71
126.56
128.22
128.84
128.88
129.14
131.90
132.27
134.31
3g
O
N H
O
O
CH
3CH
313
C NMR, 75 MHz, C
6D
6-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
3.07
1.00
1.08
1.02
1.08
3.18
0.96
0.79
2.18
1.09
1.08
0.98
0.99 1.91
6.28
6.53
6.53
6.55
6.56
6.56
6.58
6.58
6.60
6.63
6.78
6.81
6.83
6.95
6.98
7.00
7.00
7.02
7.02
7.03
7.04
7.09
7.10
7.12
7.13
7.17
7.25
7.25
7.27
7.28
7.307.30
7.30
7.32
7.33
7.41
7.44
7.52
7.54
8.02
9.96
9.98
3h
1
H NMR, 300 MHz, C
6D
66.2 6.3 6.4 6.5 6.6 6.7 6.8 6.9 7.0 7.1 7.2 7.3 7.4 7.5 7.6 7.7 7.8 7.9 8.0
ppm
1.00
1.08
1.02
1.08
3.18
0.96
1.00
2.18
1.09
1.08
0.98 6.28
6.53
6.53
6.55
6.56
6.56
6.58
6.58
6.60
6.63
6.78
6.81
6.83
6.90
6.95
6.98
7.00
7.00
7.02
7.02
7.03
7.04
7.09
7.10
7.12
7.13
7.17
7.25
7.25
7.27
7.28
7.30
7.30
7.30
7.32
7.33
7.41
7.44
7.527.54
8.01
8.02
O
N H
O
CH
3F F
F
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
27.09
81.00
102.24
113.59
116.84
119.43
122.09
122.14122.19
122.25
122.67
124.76
124.92
126.28
126.76
127.07
128.62
129.06
129.99
130.38
130.56
130.81
131.22
132.45
134.39
136.00
147.74
148.90
200.43
13
C NMR, 75 MHz, C
6D
63h
121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137
ppm
122.09
122.14
122.19
122.25
122.67
124.76
124.92
126.28
126.76
127.07
128.12
128.62
129.06
129.99
130.38
130.56
130.81
131.22
132.45
134.39
136.00
O
N H
O
CH
3F F
F
-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
3.14
0.99
1.03
1.01
4.56
2.30
2.35
3.18
1.02 1.90
6.21
6.48
6.48
6.51
6.53
6.53
6.55
6.58
6.93
6.96
6.98
7.02
7.06
7.09
7.18
7.21
7.21
7.23
7.26
7.31
7.34
7.36
9.96
9.99 1
H NMR, 300 MHz, C
6D
66.5 7.0
7.5
ppm
0.99
1.03
1.01
4.56
2.30
2.35
3.18 6.21
6.48
6.48
6.51
6.536.53
6.55
6.58
6.93
6.96
6.98
7.02
7.06
7.09
7.18
7.21
7.21
7.23
7.26
7.31
7.34
7.36
O
N H
Cl
O
CH
33i
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
27.11
81.13
101.22
113.53
116.66
119.46
124.46
124.80
126.55
126.86
128.33
129.02
130.99
132.39
133.55
134.24
134.33
147.99
149.65
200.31
124 125
126 127
128 129
130 131
132 133
134 135
ppm
124.46
124.80
126.55
126.86
128.33
129.02
130.99
132.39
133.55
134.24
134.33
3i
13
C NMR, 75 MHz, C
6D
6O
N H
Cl
O
CH
3-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
3.35
1.00
1.07
1.05
1.04
2.30
3.20
2.23
1.96
1.03 1.93
6.22
6.50
6.50
6.52
6.52
6.53
6.55
6.55
6.58
6.60
6.70
6.71
6.72
6.73
6.94
6.94
6.96
6.97
6.97
6.99
7.00
7.05
7.05
7.07
7.07
7.08
7.10
7.20
7.22
7.22
7.23
7.25
7.257.26
7.28
7.28
7.39
7.40
7.40
7.41
7.41
10.01
10.03 1
H NMR, 300 MHz, C
6D
63j
6.2 6.3 6.4 6.5 6.6 6.7 6.8 6.9 7.0 7.1 7.2 7.3 7.4
ppm
1.00
1.07
1.05
1.04
2.30
3.20
2.23
1.96 6.22
6.50
6.50
6.52
6.52
6.53
6.55
6.55
6.58
6.60
6.70
6.71
6.72
6.73
6.94
6.946.96
6.97
6.97
6.99
7.00
7.05
7.05
7.07
7.07
7.08
7.10
7.20
7.22
7.22
7.23
7.25
7.25
7.26
7.28
7.28
7.39
7.40
7.40
7.41
7.41
O
N H
S
O
CH
30 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
27.11
81.04
100.68
113.60
116.49
119.42
122.44
124.27
124.77
125.53
126.47
127.49
128.97
131.30
132.35
134.27
137.60
147.68
148.12
200.23
13
C NMR, 75 MHz, C
6D
63j
122 123 124 125 126 127 128 129 130 131 132 133 134
ppm
122.44
124.27
124.77
125.53
126.47
127.49
128.97
131.30
132.35
134.27
O
N H
S
O
CH
3-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
2.98
2.48
4.12
1.18
0.96
1.96
1.04
1.08
1.05
1.18
1.04
1.00
1.00
0.96 0.69
0.72
0.74
1.35
1.371.40
1.42
1.44
1.47
1.92
1.95
1.97
1.98
2.00
2.02
2.07
2.10
2.12
2.14
2.17
2.19
5.64
6.48
6.50
6.50
6.52
6.53
6.53
6.55
6.556.87
6.90
6.92
6.95
6.95
6.97
6.97
7.00
7.02
7.06
7.06
7.08
7.09
7.10
7.11
7.19
7.19
7.21
7.22
7.22
7.24
7.24
7.30
7.31
7.33
7.33
7.37
7.40
9.93
9.95
1
H NMR, 300 MHz, C
6D
6O
N H
CH
3C H
33k O
6.4 6.5 6.6 6.7 6.8 6.9 7.0 7.1 7.2 7.3 7.4 7.5
ppm
1.96
1.04
1.08
1.05
1.18
1.04
1.00
1.00 6.48
6.50
6.50
6.52
6.53
6.53
6.55
6.55
6.87
6.90
6.92
6.93
6.95
6.95
6.97
6.97
7.00
7.02
7.067.06
7.08
7.09
7.10
7.117.19
7.21
7.22
7.22
7.24
7.24
7.30
7.31
7.33
7.33
7.37
7.40
1.5 2.0
ppm
2.48
4.12
1.18 1.35
1.37
1.40
1.42
1.44
1.47
1.92
1.95
1.97
1.98
2.00
2.02
2.07
2.10
2.12
2.14
2.17
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
13.07
20.09
27.22
35.90
80.60
101.04
113.78
116.27
119.19
123.41
124.89
125.89
126.81
128.89
131.24
132.26
134.28
148.26
154.72
200.31
O
N H
CH
3C H
33 O
k
13
C NMR, 75 MHz, C
6D
6123 124 125 126 127 128 129 130 131 132 133 134
ppm
123.41
124.89
125.89
126.81
128.89
131.24
132.26
134.28
-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
ppm
2.08
1.02
1.09
1.16
3.03
0.92
1.02
0.92
1.14
0.92
1.04
1.06
1.89
1.00
0.94 0.31
0.32
0.32
0.33
0.33
0.34
0.34
0.35
0.36
0.37
0.38
0.39
0.40
0.40
0.41
0.41
0.42
0.42
0.43
0.43
0.58
0.59
0.590.60
0.60
0.61
0.61
0.62
0.62
0.63
0.63
0.64
0.98
0.99
1.00
1.00
1.01
1.01
1.02
1.02
1.03
1.03
1.04
1.04
1.05
1.26
1.28
1.29
1.30
1.31
1.32
1.32
1.33
1.95
5.79
6.36
6.39
6.49
6.49
6.51
6.51
6.52
6.53
6.54
6.87
6.89
6.92
6.93
6.95
6.95
6.98
7.00
7.05
7.06
7.08
7.08
7.10
7.11
7.18
7.18
7.20
7.20
7.28
7.28
7.31
9.899.91
3l
1
H NMR, 300 MHz, C
6D
66.85 6.90 6.95 7.00 7.05 7.10 7.15 7.20 7.25 7.30
ppm
1.14
0.92
1.04
1.06
1.89
1.00 6.87
6.89
6.92
6.93
6.95
6.95
6.98
7.00
7.05
7.06
7.08
7.08
7.10
7.11
7.18
7.18
7.20
7.20
7.28
7.28
7.31
0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2 1.3
ppm
2.08
1.02
1.09
1.16 0.31
0.32
0.33
0.34
0.34
0.35
0.36
0.37
0.38
0.39
0.40
0.40
0.41
0.42
0.43
0.43
0.60
0.61
0.62
0.62
0.63
1.00
1.00
1.01
1.01
1.02
1.03
1.28
1.29
1.31
1.32
1.33
O
N H
O
CH
30 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
4.33
6.30
14.54
27.29
80.85
99.95
113.67
116.48
119.43
123.14
124.91
125.65
127.29
129.10
131.73
132.46
134.39
148.34
154.78
200.24
3l
13
C NMR, 75 MHz, C
6D
6124.0 124.5
125.0 125.5
126.0 126.5
127.0 127.5
128.0 128.5
129.0
ppm
124.91
125.65
127.29
129.10
O
N H
O
CH
3-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
2.17
6.54
3.13
1.00
1.00
0.99
0.97
1.07
1.08
1.04
1.01
1.03
0.96
1.03
0.97 1.33
1.35
1.35
1.52
1.53
1.55
1.57
1.63
1.66
1.68
1.70
1.71
1.99
2.48
2.50
2.53
2.56
2.58
5.73
6.46
6.49
6.50
6.51
6.53
6.53
6.53
6.55
6.56
6.89
6.92
6.95
6.96
6.98
6.98
7.01
7.03
7.06
7.07
7.09
7.09
7.11
7.11
7.207.20
7.22
7.23
7.23
7.25
7.26
7.31
7.31
7.34
7.34
7.35
7.38
9.90
9.92
3m
1
H NMR, 300 MHz, C
6D
66.5 6.6
6.7 6.8
6.9 7.0
7.1 7.2
7.3 7.4
ppm
0.99
0.97
1.07
1.08
1.04
1.01
1.03
0.96
1.03 6.46
6.49
6.50
6.51
6.53
6.53
6.53
6.55
6.56
6.89
6.92
6.95
6.96
6.98
6.98
7.01
7.03
7.06
7.07
7.09
7.09
7.11
7.11
7.20
7.20
7.22
7.23
7.23
7.25
7.26
7.31
7.31
7.34
7.34
7.35
7.38
2.4 2.5
2.6 2.7
ppm
0.99 2.48
2.50
2.53
2.56
2.58
O
N H
O
CH
30 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
25.69
25.81
27.36
30.45
30.62
43.95
80.78
99.55
113.98
116.43
119.32
123.70
124.98
126.00
129.03
131.52
132.45
134.37
148.50
157.85
200.32
30.3 30.6
ppm
30.45
30.62
3m
13
C NMR, 75 MHz, C
6D
625.5 26.1
ppm
25.69
25.81
O
N H
O
CH
3-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
3.01
1.00
2.08
1.20
7.80
1.12
1.10
1.04
1.02 3.15
6.22
6.25
6.27
6.44
6.47
6.80
6.82
6.85
6.95
6.97
6.99
7.04
7.06
7.31
7.34
7.78
7.79
7.81
7.82
7.91
7.91
7.937.94
8.70
8.72
3n
1
H NMR, 300 MHz, C
6D
66.2 6.4 6.6 6.8 7.0 7.2 7.4 7.6 7.8
ppm
1.00
2.08
1.20
7.80
1.12
1.10
1.04 6.22
6.25
6.27
6.44
6.47
6.80
6.82
6.85
6.95
6.97
6.99
7.04
7.06
7.31
7.34
7.78
7.79
7.81
7.82
7.91
7.91
7.93
7.94
O
N H
O C H
3N
+O
O
-0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
54.52
80.48
106.21
111.10
115.60
117.20
120.26
123.82
124.58
124.85
126.35
126.78
127.16
128.63
129.32
129.52
131.41
133.85135.12
142.42
147.89
157.72
13
C NMR, 75 MHz, C
6D
63n
126.0 126.5
127.0 127.5
128.0 128.5
ppm
126.35
126.78
127.16
128.63
O
N H
O C H
3N
+O
O
--0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
1.02
0.97
1.04
0.91
4.10
1.06
1.15
1.13
0.84
0.86
0.93 6.17
6.23
6.25
6.28
6.34
6.36
6.72
6.73
6.74
6.75
6.89
6.91
6.93
6.96
6.99
7.02
7.03
7.07
7.09
7.12
7.22
7.25
7.33
7.34
7.89
7.89
7.92
7.92
8.56
8.58
1
H NMR, 300 MHz, C
6D
6O
N H
S
N
+O
O
-3o
traces of diispropyl ether
traces of diispropyl ether
DCM
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
81.09
101.13
115.75
117.97
123.03
125.05
125.20
125.31
126.41
127.05
127.27
127.44
129.97
131.38
134.42
135.68
137.68
142.62
147.77
O
N H
S
N
+O
O
-3o
13
C NMR, 75 MHz, C
6D
6125 126
127 128
129 130
131
ppm
125.05
125.20
125.31
126.41
127.05
127.27
127.44
129.97
131.38
-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
1.10
1.00
1.02
2.12
5.00
2.01
1.92 5.35
5.37
6.47
6.72
6.75
7.00
7.03
7.26
7.29
7.30
7.30
7.31
7.32
7.32
7.32
7.32
7.40
7.41
7.42
7.42
7.43
7.44
7.44
7.45
7.46
7.47
7.48
8.15
8.19 1
H NMR, 300 MHz, CCl
2D
23p
O
N H
S
N
+O
O
-80 85
90 95
100 105
110 115
120 125
130 135
140 145
150 155
ppm
80.60
100.23
113.14
122.92
124.51
124.59
125.45
125.96
126.33
126.63
126.80
129.73
130.64
136.92
140.00
147.00
150.30
3 p
O
N H
S
N
+O
O
-13
C NMR, 75 MHz, CCl
2D
2127.0 126.5 126.0 125.5 125.0 124.5 124.0 123.5 123.0
ppm
122.92
124.51
124.59
125.45
125.96
126.33
126.63
126.80
-0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
9.07
1.03
1.00
1.99
2.09
2.11
1.06
1.36
0.98
0.94 1.31
1.32
1.33
1.34
1.37
1.37
1.38
1.40
1.43
1.54
1.56
1.57
1.58
1.60
1.60
1.61
1.62
1.62
1.63
1.64
2.40
2.43
2.46
2.48
2.51
5.67
6.24
6.24
6.25
6.26
6.27
6.27
6.28
6.29
6.30
6.84
6.86
6.88
6.92
6.93
6.95
6.95
6.97
6.98
6.98
7.00
7.01
7.06
7.06
7.087.09
7.11
7.11
7.20
7.22
7.96
7.96
7.99
7.99
8.51
8.54
3q
1
H NMR, 300 MHz, C
6D
62.35 2.40
2.45 2.50
2.55 2.60
ppm
1.03 2.40
2.43
2.46
2.48
2.51
6.8 6.9
7.0 7.1
7.2 7.3
ppm
2.09
2.11
1.06
1.36 6.84
6.86
6.88
6.92
6.93
6.95
6.95
6.97
6.98
6.98
7.00
7.01
7.06
7.06
7.08
7.09
7.11
7.11
7.20
7.22
O
N H
N
+O
O
-0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
25.60
25.72
30.36
30.53
43.77
80.25
99.63
115.71
117.44
123.95
125.01
126.26
126.50
126.55
129.49
131.05
133.90
135.21
142.44
157.39
3 q
13
C NMR, 75 MHz, C
6D
630.0 30.5
ppm
30.36
30.53
25.5 25.6 25.7 25.8
ppm
25.60
25.72
124 125
126 127
128 129
130 131
ppm
123.95
125.01
126.26
126.50
126.55
129.49
131.05
O
N H
N
+O
O
--0.5 0.0
0.5 1.0
1.5 2.0
2.5 3.0
3.5 4.0
4.5 5.0
5.5 6.0
6.5 7.0
7.5 8.0
8.5 9.0
9.5 10.0
10.5
ppm
8.74
1.05
0.95
1.09
1.06
1.91
1.00
0.98
1.04
1.02
1.86 1.33
1.33
1.34
1.35
1.35
1.36
1.37
1.40
1.55
1.55
1.56
1.571.59
1.60
1.61
1.62
1.64
2.41
2.44
2.46
2.49
2.52
4.34
4.37
5.67
6.03
6.06
6.07
6.10
6.70
6.70
6.70
6.71
6.72
6.73
6.73
6.73
6.90
6.92
6.94
6.94
6.966.97
6.99
6.99
7.10
7.11
7.13
7.13
7.94
7.97
1
H NMR, 300 MHz, C
6D
63r
5.9 6.0 6.1 6.2 6.3 6.4 6.5 6.6 6.7 6.8 6.9 7.0 7.1 7.2
ppm
1.06
1.91
1.00
0.98
1.04
1.02 6.03
6.06
6.07
6.10
6.70
6.70
6.70
6.71
6.72
6.73
6.73
6.73
6.90
6.92
6.94
6.94
6.96
6.97
6.996.99
7.10
7.11
7.13
7.13
O
N H
N
+O
O
-traces of diispropyl ether
traces of diispropyl ether
0 10
20 30
40 50
60 70
80 90
100 110
120 130
140 150
160 170
180 190
200
ppm
25.52
25.66
30.37
43.68
80.05
98.68
112.69
123.48
125.36
125.49
125.86
126.17
129.35
131.10
140.18
149.68
157.94
3r
O
N H
N
+O
O
- 13C NMR, 75 MHz, C
6D
6123 124
125 126
127 128
129 130
131
ppm
123.48
125.36
125.49
125.86
126.17
129.35
131.10
24.8 25.6
ppm
25.52
25.66
