Health Promotion and Disease Prevention under the Aquino Health Agenda by Usec. Teodoro Herbosa
Supporting information (Part II) · RG 1625.5 DW 27.800 usec DE 6.50 usec TE 295.7 K D1 2.00000000...
45
S1 NHC-Mediated Cross-Coupling of Sugar-Derived Cyclic Nitrones with Enals: General and Efficient Synthesis of Polyhydroxylated Pyrrolizidines and Indolizidines Wen-Yuan Xu, a, c Ren Iwaki, b Yue-Mei Jia, a Wei Zhang, a Atsushi Kato* b and Chu-Yi Yu* a a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100191, China. E-mail: [email protected] b Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan c University of Chinese Academy of Sciences, Beijing 100049, China Supporting information (Part II) Contents Page Number Section II. NMR Spectra of 7aa, 8 and 9 S2-S45 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2013
Transcript of Supporting information (Part II) · RG 1625.5 DW 27.800 usec DE 6.50 usec TE 295.7 K D1 2.00000000...
S1
NHC-Mediated Cross-Coupling of Sugar-Derived Cyclic Nitrones with
Enals: General and Efficient Synthesis of Polyhydroxylated Pyrrolizidines
and Indolizidines
Wen-Yuan Xu, a, c
Ren Iwaki,b Yue-Mei Jia,
a Wei Zhang,
a Atsushi Kato*
b and Chu-Yi
Yu*a
a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function,
Institute of Chemistry, Chinese Academy of Sciences, Beijing 100191, China. E-mail:
[email protected] b Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan c University of Chinese Academy of Sciences, Beijing 100049, China
Supporting information (Part II)
Contents Page Number
Section II. NMR Spectra of 7aa, 8 and 9 S2-S45
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S2
Section II. NMR Spectra of 7aa, 8 and 9
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
2.7
34
2.7
63
2.7
88
2.8
16
2.8
76
2.9
15
2.9
28
2.9
68
3.2
24
3.2
39
3.2
67
3.2
81
3.3
94
3.4
23
3.4
33
3.4
53
3.4
62
3.4
91
3.8
86
3.9
97
4.0
07
4.0
27
4.0
36
4.1
34
4.1
41
4.1
49
4.1
56
4.1
72
4.3
29
4.4
38
4.4
77
4.6
17
4.6
57
7.0
75
7.0
83
7.0
93
7.1
06
7.2
88
7.2
98
7.3
09
7.3
28
7.3
34
7.3
52
7.3
78
7.3
98
7.4
03
0.97
1.00
0.97
0.98
0.98
0.99
1.98
1.98
1.01
1.00
2.00
12.94
NAME xwy-542p1EXPNO 10PROCNO 1Date_ 20120208Time 22.06INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 32768SOLVENT CDCl3NS 16DS 0SWH 8992.806 HzFIDRES 0.274439 HzAQ 1.8219508 secRG 90.5DW 55.600 usecDE 8.00 usecTE 292.9 KD1 2.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.80 usecPL1 3.00 dBSFO1 300.1318008 MHzSI 32768SF 300.1300000 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
2030405060708090100110120130140150160170180 ppm
41.89
46.69
46.90
71.21
71.56
72.58
76.74
77.16
77.58
83.02
85.64
127.43
127.75
127.92
127.96
128.02
128.51
128.62
129.03
137.22
137.52
140.13
175.57
NAME xwy-542p1EXPNO 20PROCNO 1Date_ 20120209Time 15.13INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 82DS 4SWH 17985.611 HzFIDRES 0.274439 HzAQ 1.8219508 secRG 1149.4DW 27.800 usecDE 6.50 usecTE 296.1 KD1 2.00000000 secD11 0.03000000 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 12.50 usecPL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 100.00 usecPL2 3.00 dBPL12 22.33 dBPL13 23.00 dBSFO2 300.1312005 MHzSI 32768SF 75.4677455 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S3
2030405060708090100110120130140150160 ppm41.84
46.65
46.85
71.17
71.51
72.53
82.97
85.59
127.38
127.70
127.88
127.92
127.98
128.46
128.58
128.98
NAME xwy-542p1EXPNO 21PROCNO 1Date_ 20120209Time 15.18INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG dept135TD 65536SOLVENT CDCl3NS 26DS 4SWH 17985.611 HzFIDRES 0.274439 HzAQ 1.8219508 secRG 16384DW 27.800 usecDE 6.50 usecTE 296.1 KCNST2 145.0000000D1 2.00000000 secD2 0.00344828 secD12 0.00002000 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 12.50 usecP2 25.00 usecPL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HP3 10.80 usecP4 21.60 usecPCPD2 100.00 usecPL2 3.00 dBPL12 22.33 dBSFO2 300.1312005 MHzSI 32768SF 75.4677490 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
ppm
2.62.83.03.23.43.63.84.04.24.44.6 ppm
2.6
2.8
3.0
3.2
3.4
3.6
3.8
4.0
4.2
4.4
4.6
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S4
ppm
2.83.03.23.43.63.84.04.24.44.6 ppm
40
45
50
55
60
65
70
75
80
85
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S5
NOESY experiment and molecular model from Chem3D of 7aa
ppm
3.03.23.43.63.84.04.24.44.6 ppm
3.0
3.2
3.4
3.6
3.8
4.0
4.2
4.4
4.6
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S6
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.8
90
2.9
01
2.9
18
2.9
37
2.9
55
3.0
11
3.0
30
3.0
49
3.2
58
3.2
94
3.4
86
3.5
77
3.5
97
3.6
87
3.7
09
3.7
36
3.7
54
3.8
86
3.9
23
3.9
90
4.0
27
4.2
79
4.3
19
4.4
04
4.4
44
5.6
25
6.7
76
6.7
82
6.7
95
6.8
07
7.0
74
7.1
00
7.1
08
7.1
19
7.1
22
7.1
48
7.1
55
7.1
78
7.1
84
7.2
04
7.2
15
7.2
42
0.9
8
0.6
0
1.3
7
1.0
2
1.0
4
2.9
4
1.0
6
2.0
3
1.0
4
1.0
2
1.0
0
1.0
4
0.9
1
1.9
6
13
.60
NAME xwy-503cEXPNO 10
PROCNO 1Date_ 20120414
Time 15.07
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 4DS 0
SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 35.9
DW 55.600 usecDE 8.00 usec
TE 297.6 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.80 usecPL1 3.00 dB
SFO1 300.1324010 MHz
SI 32768SF 300.1300614 MHz
WDW EMSSB 0
LB 0.30 Hz
GB 0PC 1.00
405060708090100110120130140150160170180 ppm
34
.93
41
.00
51
.75
59
.75
70
.85
71
.28
76
.72
77
.14
77
.33
77
.57
79
.30
83
.47
12
6.6
6
12
7.5
9
12
7.7
1
12
8.0
7
12
8.1
7
12
8.4
1
12
8.4
6
13
7.5
0
13
7.9
9
14
1.0
2
17
4.2
9
NAME xwy-503cEXPNO 11
PROCNO 1Date_ 20120414
Time 15.09
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 67DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 574.7
DW 27.800 usecDE 6.50 usec
TE 297.9 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 12.50 usec
PL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
PCPD2 100.00 usecPL2 3.00 dB
PL12 22.33 dBPL13 23.00 dB
SFO2 300.1312005 MHz
SI 32768SF 75.4677572 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S7
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.8
64
2.8
91
2.9
14
2.9
33
2.9
50
2.9
70
2.9
92
3.0
11
3.2
76
3.3
12
3.5
22
3.5
79
3.5
98
3.6
58
3.6
74
3.7
64
3.7
81
3.9
52
3.9
90
4.0
64
4.1
02
4.3
10
4.3
50
4.4
36
4.4
76
5.4
70
6.7
17
6.7
46
6.8
28
6.8
35
6.8
47
6.8
59
7.0
52
7.0
81
7.1
35
7.1
43
7.1
54
7.1
57
7.2
27
7.2
34
7.2
42
7.2
65
1.0
8
1.1
1
1.9
4
1.0
7
2.9
5
1.1
2
4.1
1
0.9
7
0.9
8
0.9
6
1.0
1
1.0
0
0.8
3
2.0
3
1.9
4
1.9
9
3.0
2
5.5
4
NAME xwy-536bEXPNO 20
PROCNO 1Date_ 20120418
Time 9.04
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 16DS 0
SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 45.3
DW 55.600 usecDE 8.00 usec
TE 295.5 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.80 usecPL1 3.00 dB
SFO1 300.1324010 MHz
SI 32768SF 300.1300410 MHz
WDW EMSSB 0
LB 0.30 Hz
GB 0PC 1.00
405060708090100110120130140150160170180 ppm
35
.38
40
.39
51
.85
55
.25
59
.86
70
.96
71
.44
76
.74
77
.16
77
.36
77
.59
79
.30
83
.75
11
3.9
3
12
7.7
1
12
7.7
8
12
7.8
0
12
7.8
4
12
8.2
6
12
8.5
0
12
9.0
4
13
3.0
5
13
7.5
7
13
8.0
3
15
8.4
0
17
4.4
1
NAME xwy-536bEXPNO 21
PROCNO 1Date_ 20120418
Time 9.09
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 101DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 1625.5
DW 27.800 usecDE 6.50 usec
TE 295.7 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 12.50 usec
PL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
PCPD2 100.00 usecPL2 3.00 dB
PL12 22.33 dBPL13 23.00 dB
SFO2 300.1312005 MHz
SI 32768SF 75.4677470 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S8
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.6
31
2.6
53
2.6
85
2.7
07
2.8
66
2.8
92
2.9
20
2.9
46
3.0
19
3.0
37
3.0
54
3.0
72
3.1
79
3.1
97
3.2
15
3.3
73
3.4
08
3.6
36
3.7
32
3.7
51
3.8
37
3.8
55
3.8
85
3.9
03
4.1
76
4.1
89
4.2
27
4.4
00
4.4
40
4.5
02
4.5
42
5.6
60
6.0
96
6.1
06
6.2
65
6.2
71
6.2
75
6.2
82
7.0
77
7.0
81
7.0
91
7.0
99
7.1
07
7.2
49
7.2
72
7.2
90
7.3
06
7.3
08
7.3
12
7.3
42
7.3
55
0.9
5
0.9
9
1.0
0
1.0
0
1.0
4
2.9
6
1.0
6
2.1
6
2.1
1
1.0
8
1.1
0
0.9
8
1.0
4
1.0
7
2.0
0
9.3
3
NAME xwy-504cEXPNO 10
PROCNO 1Date_ 20120418
Time 17.04
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 11
DS 0SWH 8992.806 Hz
FIDRES 0.137219 Hz
AQ 3.6438515 secRG 57
DW 55.600 usecDE 8.00 usec
TE 295.3 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 10.80 usec
PL1 3.00 dBSFO1 300.1324010 MHz
SI 32768
SF 300.1300162 MHzWDW EM
SSB 0LB 0.30 Hz
GB 0
PC 1.00
405060708090100110120130140150160170180 ppm
33
.45
35
.25
52
.00
59
.78
70
.94
71
.61
75
.34
76
.74
77
.16
77
.58
79
.32
83
.39
10
6.1
2
11
0.2
8
12
7.7
7
12
7.8
4
12
8.3
3
12
8.5
1
13
7.7
2
13
8.0
0
14
1.6
6
15
4.9
0
17
4.1
4
NAME xwy-504cEXPNO 12
PROCNO 1Date_ 20120418
Time 17.13
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 80DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 812.7
DW 27.800 usecDE 6.50 usec
TE 295.5 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 12.50 usec
PL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
PCPD2 100.00 usecPL2 3.00 dB
PL12 22.33 dBPL13 23.00 dB
SFO2 300.1312005 MHz
SI 32768SF 75.4677458 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S9
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
1.6
22
1.6
41
2.2
77
2.3
02
2.3
29
2.3
54
2.5
51
2.5
74
2.6
03
2.6
26
2.8
63
2.8
79
2.8
84
2.9
00
3.0
05
3.0
25
3.0
40
3.0
60
3.0
75
3.3
65
3.4
00
3.6
20
3.6
65
3.6
87
3.8
94
3.9
13
4.3
79
4.4
10
4.4
17
4.4
49
4.4
55
4.4
71
4.4
94
4.5
21
4.5
61
5.3
99
5.4
02
5.4
27
5.4
34
5.4
52
5.4
72
5.5
23
7.2
61
7.2
72
7.2
85
7.3
06
7.3
16
7.3
24
7.3
29
7.3
41
7.3
56
3.0
5
1.0
0
1.0
3
1.0
2
1.9
4
1.0
6
3.0
1
1.0
0
0.9
8
4.0
8
2.1
0
0.8
7
10
.35
NAME xwy-569EXPNO 10
PROCNO 1Date_ 20120422
Time 17.10
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 16DS 0
SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 40.3
DW 55.600 usecDE 8.00 usec
TE 295.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.80 usecPL1 3.00 dB
SFO1 300.1324010 MHzSI 32768
SF 300.1300152 MHz
WDW EMSSB 0
LB 0.30 Hz
GB 0PC 1.00
30405060708090100110120130140150160170180 ppm
18
.12
35
.72
39
.36
51
.67
60
.39
71
.01
71
.63
75
.52
76
.72
77
.15
77
.57
79
.35
83
.42
12
6.7
6
12
7.8
2
12
7.9
4
12
8.4
3
12
8.4
7
13
0.5
8
13
7.7
4
13
7.9
5
17
4.4
0
NAME xwy-569EXPNO 11
PROCNO 1Date_ 20120422
Time 17.12
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 40DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 812.7
DW 27.800 usecDE 6.50 usec
TE 295.5 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 12.50 usec
PL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
PCPD2 100.00 usecPL2 3.00 dB
PL12 22.33 dBPL13 23.00 dB
SFO2 300.1312005 MHz
SI 32768SF 75.4677487 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S10
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.6
10
2.6
43
2.6
64
2.9
30
2.9
58
3.0
11
3.3
82
3.4
03
3.4
23
3.5
57
3.5
74
3.5
96
3.6
04
3.6
29
3.7
54
3.7
61
3.7
76
3.7
97
3.8
76
3.8
88
3.9
04
3.9
16
3.9
61
3.9
93
4.0
31
4.0
67
4.1
05
4.3
94
4.4
22
4.4
34
4.4
62
4.4
79
4.5
20
4.5
70
4.6
10
5.5
71
6.8
46
6.8
53
6.8
64
6.8
76
7.1
58
7.1
86
7.1
95
7.2
07
7.2
33
7.2
48
7.2
58
7.2
80
7.2
95
7.3
03
7.3
21
0.9
6
1.0
1
0.9
6
4.9
7
2.0
5
1.1
0
1.0
0
2.1
2
3.1
5
1.0
9
1.0
1
2.1
6
19
.06
NAME xwy-575EXPNO 10
PROCNO 1Date_ 20120419
Time 22.51
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 15DS 0
SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 35.9
DW 55.600 usecDE 8.00 usec
TE 295.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.80 usecPL1 3.00 dB
SFO1 300.1324010 MHz
SI 32768SF 300.1300362 MHz
WDW EMSSB 0
LB 0.30 Hz
GB 0PC 1.00
405060708090100110120130140150160170180 ppm
35
.20
41
.47
51
.75
66
.14
68
.16
71
.18
71
.27
73
.32
74
.31
76
.73
77
.16
77
.58
82
.74
83
.83
12
6.6
8
12
7.5
2
12
7.5
8
12
7.6
9
12
7.7
4
12
8.0
7
12
8.1
6
12
8.3
5
12
8.5
0
13
7.7
2
13
8.1
5
13
8.3
2
14
1.2
2
17
4.2
9
NAME xwy-575EXPNO 12
PROCNO 1Date_ 20120419
Time 22.57
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 78DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 812.7
DW 27.800 usecDE 6.50 usec
TE 295.5 K
D1 2.00000000 secD11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 12.50 usec
PL1 2.00 dB
SFO1 75.4752953 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1H
PCPD2 100.00 usecPL2 3.00 dB
PL12 22.33 dB
PL13 23.00 dBSFO2 300.1312005 MHz
SI 32768
SF 75.4677543 MHzWDW EM
SSB 0
LB 1.00 HzGB 0
PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S11
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 1.0 0.5 0.0 ppm
2.6
19
2.6
41
2.9
02
2.9
29
3.3
48
3.3
68
3.3
88
3.5
51
3.5
75
3.6
90
3.7
07
3.7
65
3.7
83
3.7
86
3.8
77
3.8
87
3.9
03
3.9
13
3.9
69
4.0
49
4.0
86
4.1
24
4.1
62
4.3
98
4.4
26
4.4
38
4.4
66
4.4
84
4.5
24
4.5
69
4.6
09
5.6
32
6.7
69
6.7
98
6.8
92
6.8
99
6.9
11
6.9
23
7.0
94
7.1
23
7.1
62
7.1
99
7.2
07
7.2
20
7.2
34
7.2
53
7.2
65
7.2
71
7.2
85
7.3
01
7.3
17
1.0
3
1.0
0
1.0
15
.16
4.2
51
.21
1.1
51
.14
2.2
4
3.3
2
1.2
9
1.0
7
2.2
02
.15
2.3
1
14
.13
30405060708090100110120130140150160170180 ppm
35
.53
40
.75
51
.68
55
.14
66
.18
68
.19
71
.17
71
.29
73
.28
74
.26
76
.72
77
.15
77
.57
82
.75
83
.94
11
3.8
31
27
.53
12
7.5
61
27
.67
12
7.7
11
28
.05
12
8.1
31
28
.32
12
8.9
61
33
.12
13
7.7
31
38
.11
13
8.2
9
15
8.3
0
17
4.2
3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S12
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 1.0 0.5 0.0 ppm
2.6
25
2.6
59
2.6
79
2.8
51
2.8
77
3.4
67
3.4
86
3.5
05
3.5
95
3.6
10
3.6
20
3.7
79
3.7
99
3.8
30
3.8
54
3.9
27
3.9
35
3.9
59
4.1
46
4.1
58
4.3
95
4.4
36
4.4
52
4.4
92
4.5
08
4.5
50
4.5
56
4.5
96
5.5
45
6.0
63
6.0
73
6.2
48
6.2
54
6.2
58
6.2
65
7.0
24
7.0
30
7.0
44
7.0
55
7.2
06
7.2
30
7.2
36
7.2
47
7.2
53
7.2
57
7.2
69
7.2
86
7.2
91
7.3
07
7.3
18
7.3
44
0.9
7
1.0
0
1.0
1
4.8
0
2.0
71
.95
1.9
5
4.3
9
0.9
1
0.9
8
0.9
8
1.9
8
14
.48
2030405060708090100110120130140150160170180 ppm
33
.44
35
.69
51
.95
65
.86
67
.96
71
.19
71
.53
72
.31
73
.44
76
.75
77
.17
77
.60
82
.55
83
.43
10
6.0
6
11
0.2
5
12
7.6
21
27
.67
12
7.7
21
27
.86
12
8.0
71
28
.27
12
8.3
91
28
.41
13
7.8
91
38
.18
13
8.3
91
41
.60
15
4.9
5
17
4.1
6
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S13
2.02.53.03.54.04.55.05.56.06.57.07.5 ppm
1.6
17
1.6
36
2.2
40
2.2
62
2.2
92
2.3
14
2.5
22
2.5
47
2.5
73
2.5
98
3.0
20
3.1
49
3.1
67
3.1
72
3.1
89
3.5
95
3.6
06
3.7
25
3.7
32
3.7
48
3.7
55
3.9
04
3.9
20
3.9
80
4.3
22
4.3
61
4.3
83
4.4
19
4.4
59
4.5
25
4.5
34
4.5
75
4.6
15
4.6
74
5.3
57
5.3
67
5.3
76
5.3
80
5.4
07
5.4
47
5.4
67
7.2
06
7.2
25
7.2
34
7.2
61
7.2
69
7.2
86
7.2
97
7.3
10
7.3
46
7.3
60
3.0
7
1.0
1
0.9
8
0.9
6
1.0
0
5.0
6
0.9
7
0.9
8
1.0
7
3.2
8
3.0
6
0.7
1
1.3
9
1.0
1
14
.98
NAME xwy-508bEXPNO 10
PROCNO 1Date_ 20120427
Time 21.39
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 12
DS 0SWH 8992.806 Hz
FIDRES 0.137219 Hz
AQ 3.6438515 secRG 128
DW 55.600 usecDE 8.00 usec
TE 300.1 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 10.80 usec
PL1 3.00 dBSFO1 300.1324010 MHz
SI 32768
SF 300.1300136 MHzWDW EM
SSB 0LB 0.30 Hz
GB 0
PC 1.00
2030405060708090100110120130140150160170180 ppm
18
.12
35
.62
39
.78
51
.65
65
.38
66
.28
68
.34
71
.29
71
.57
72
.53
73
.45
76
.69
77
.11
77
.54
82
.97
83
.48
12
6.6
11
27
.04
12
7.6
51
27
.72
12
7.9
81
28
.13
12
8.3
71
28
.42
12
8.6
11
30
.81
13
7.9
51
38
.19
13
8.3
5
17
4.5
2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S14
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
2.7
49
2.7
75
2.8
02
2.8
28
2.8
98
2.9
22
2.9
34
2.9
49
2.9
67
2.9
75
3.4
38
3.4
53
3.4
61
3.4
76
3.5
31
3.6
12
3.6
28
3.6
35
3.6
51
3.8
66
3.8
72
3.8
89
3.9
30
3.9
43
3.9
56
4.1
44
4.1
83
4.4
21
4.4
60
4.4
76
4.4
93
4.5
16
4.5
48
4.5
87
4.6
79
4.7
18
5.5
48
7.0
83
7.1
01
7.1
09
7.1
62
7.1
86
7.1
92
7.2
04
7.2
11
7.2
18
7.2
68
7.2
98
1.0
2
1.9
9
2.1
22
.91
1.0
7
2.0
61
.03
1.0
0
3.1
31
.10
1.0
1
0.9
6
21
.09
2030405060708090100110120130140150160170180 ppm
37
.63
42
.24
51
.58
65
.78
67
.00
72
.51
73
.39
76
.72
76
.93
77
.14
77
.43
77
.56
81
.12
12
6.8
71
27
.69
12
7.8
01
27
.87
12
7.8
91
27
.98
12
8.2
91
28
.40
12
8.4
21
28
.76
13
7.9
91
38
.15
13
8.2
31
40
.45
17
3.1
6
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S15
3.03.54.04.55.05.56.06.57.07.5 ppm
2.8
87
2.8
98
2.9
28
2.9
50
3.3
49
3.3
57
3.3
73
3.4
18
3.4
32
3.4
42
3.4
56
3.5
35
3.5
87
3.6
02
3.6
10
3.6
26
3.7
26
3.8
70
3.8
77
3.8
94
3.9
37
3.9
49
3.9
62
4.1
87
4.2
27
4.4
66
4.4
84
4.4
98
4.5
37
4.5
50
4.5
89
4.6
97
4.7
36
5.5
85
6.6
91
6.7
19
6.9
77
7.0
05
7.2
17
7.2
29
7.2
41
7.2
48
7.2
73
7.2
83
7.3
13
7.3
37
1.0
1
2.1
6
1.9
5
2.8
3
1.2
7
3.0
2
1.9
3
1.0
9
1.0
0
2.4
6
0.9
9
1.0
5
1.1
1
0.9
5
1.9
7
2.0
6
18
.61
2030405060708090100110120130140150160170180 ppm
38
.01
41
.51
51
.56
55
.17
65
.80
67
.02
72
.57
73
.41
73
.46
76
.72
77
.14
77
.56
81
.37
11
3.6
51
27
.72
12
7.8
21
27
.84
12
7.8
81
27
.92
12
8.0
41
28
.41
12
8.4
31
28
.46
12
8.5
11
29
.75
13
2.2
61
38
.01
13
8.1
51
38
.22
15
8.4
4
17
3.2
0
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S16
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.7
48
2.7
59
2.7
73
2.7
84
3.2
27
3.2
44
3.2
59
3.5
91
3.6
62
3.6
78
3.6
82
3.6
91
3.7
07
3.9
00
3.9
17
3.9
34
3.9
50
3.9
65
4.2
31
4.2
69
4.4
43
4.4
60
4.4
82
4.5
02
4.5
42
4.5
67
4.5
75
4.6
06
4.6
49
4.6
88
5.5
75
6.0
07
6.0
17
6.2
27
6.2
34
6.2
37
6.2
44
7.2
09
7.2
21
7.2
28
7.2
35
7.2
74
7.2
81
7.2
96
1.5
2
1.0
0
3.5
3
2.1
1
2.9
6
1.1
5
4.4
0
3.0
0
0.8
7
0.9
1
0.9
3
16
.91
NAME xwy-587p2EXPNO 10
PROCNO 1Date_ 20120502
Time 11.07
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 12
DS 0SWH 8992.806 Hz
FIDRES 0.137219 Hz
AQ 3.6438515 secRG 64
DW 55.600 usec
DE 8.00 usec
TE 298.1 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 10.30 usec
PL1 3.00 dBSFO1 300.1324010 MHz
SI 32768
SF 300.1300176 MHzWDW EM
SSB 0
LB 0.30 HzGB 0
PC 1.00
30405060708090100110120130140150160170 ppm
35
.27
36
.43
51
.83
65
.78
66
.80
72
.66
73
.19
73
.47
75
.30
76
.74
77
.16
77
.24
77
.59
80
.27
10
6.7
3
11
0.3
6
12
7.6
91
27
.81
12
7.8
61
27
.93
12
8.3
71
28
.43
13
8.1
51
38
.18
13
8.3
11
41
.54
15
4.5
9
17
3.0
3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S17
2.02.53.03.54.04.55.05.56.06.57.07.5 ppm
1.531
1.546
2.441
2.468
2.511
2.533
2.584
3.195
3.207
3.215
3.335
3.354
3.367
3.377
3.390
3.603
3.616
3.631
3.640
3.655
3.910
3.931
4.050
4.063
4.077
4.362
4.401
4.457
4.471
4.511
4.528
4.568
4.586
4.595
4.611
4.624
4.634
4.664
4.708
4.728
4.767
5.208
5.224
5.230
5.575
5.605
7.279
7.294
7.308
3.0
0
2.0
2
0.8
1
1.2
2
1.0
2
3.0
1
1.0
5
2.1
1
1.0
7
1.3
6
1.9
0
2.7
5
1.1
5
1.4
9
1.2
2
17
.29
NAME xwy-586cEXPNO 10
PROCNO 1
Date_ 20120522
Time 16.58
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 1DS 0
SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 64
DW 55.600 usec
DE 8.00 usec
TE 299.6 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.30 usecPL1 3.00 dB
SFO1 300.1324010 MHz
SI 32768SF 300.1300141 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0PC 1.00
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm
18
.08
37
.64
40
.83
51
.51
65
.95
67
.53
72
.72
73
.51
73
.60
76
.28
76
.72
77
.15
77
.57
77
.61
80
.97
12
7.7
9
12
7.8
3
12
7.9
4
12
8.0
1
12
8.0
7
12
8.4
5
12
8.4
9
12
9.5
6
13
8.0
9
13
8.2
1
13
8.2
4
17
3.4
1
NAME xwy-586cEXPNO 13
PROCNO 1Date_ 20120522
Time 17.06
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 137DS 4
SWH 17985.611 Hz
FIDRES 0.274439 Hz
AQ 1.8219508 sec
RG 3649.1DW 27.800 usec
DE 6.50 usec
TE 299.9 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 13C
P1 12.50 usec
PL1 2.00 dB
SFO1 75.4752953 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1HPCPD2 100.00 usec
PL2 3.00 dB
PL12 22.74 dBPL13 23.00 dB
SFO2 300.1312005 MHzSI 32768
SF 75.4677445 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S18
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
51
2.5
70
2.6
04
2.6
22
2.8
47
2.8
77
2.9
00
2.9
30
3.2
00
3.2
17
3.2
34
3.3
76
3.3
92
3.4
06
3.4
22
3.4
37
3.5
07
3.5
23
3.5
62
3.6
50
3.6
64
3.6
79
3.6
93
3.7
48
3.7
63
3.7
85
3.7
92
3.8
22
3.8
43
3.8
60
3.8
80
4.4
88
4.5
06
4.5
30
4.5
45
5.4
59
6.7
77
6.7
84
6.7
96
6.8
08
7.1
63
7.1
68
7.1
77
7.1
89
7.1
99
7.2
04
7.2
28
7.2
43
7.2
55
7.2
73
7.2
88
7.3
00
7.3
25
7.3
38
0.9
7
1.0
0
0.9
4
0.9
5
1.0
1
2.9
5
1.1
1
1.8
5
3.2
3
4.1
7
1.0
2
2.0
3
18
.06
NAME xwy-561dEXPNO 10
PROCNO 1Date_ 20120417
Time 9.02
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 16
DS 0SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 35.9
DW 55.600 usec
DE 8.00 usec
TE 295.3 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 10.80 usec
PL1 3.00 dBSFO1 300.1324010 MHz
SI 32768SF 300.1300347 MHz
WDW EM
SSB 0LB 0.30 Hz
GB 0
PC 1.00
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
34
.43
40
.82
51
.74
67
.24
67
.92
71
.08
71
.82
73
.44
76
.72
77
.15
77
.57
77
.89
79
.00
81
.71
12
6.7
21
27
.45
12
7.5
81
27
.61
12
7.6
71
27
.75
12
8.0
61
28
.18
12
8.3
61
28
.37
12
8.5
41
37
.51
13
8.2
91
38
.44
14
0.9
0
17
4.6
4
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S19
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
49
2.5
83
2.6
02
2.8
25
2.8
54
2.8
77
2.9
07
3.1
95
3.4
12
3.4
26
3.5
11
3.5
27
3.5
67
3.6
58
3.6
72
3.6
87
3.7
01
3.7
33
3.7
71
3.8
00
3.8
33
3.8
56
3.8
72
3.9
44
3.9
82
4.4
58
4.4
98
4.5
14
4.5
23
4.5
53
6.7
92
6.8
21
6.8
39
6.8
46
6.8
59
6.8
71
7.1
18
7.1
47
7.1
92
7.2
00
7.2
06
7.2
13
7.2
54
7.2
65
7.2
82
7.2
92
7.2
97
7.3
20
7.3
29
7.3
34
7.3
35
1.0
2
1.0
4
1.0
4
1.0
5
1.0
8
3.0
0
1.0
8
2.9
9
1.9
1
2.2
5
1.0
6
4.2
3
0.7
3
2.0
5
2.0
3
2.1
5
13
.58
NAME xwy-562-0707EXPNO 10
PROCNO 1Date_ 20120707
Time 9.53
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 9
DS 0
SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 45.3
DW 55.600 usec
DE 8.00 usec
TE 299.7 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.30 usecPL1 3.00 dB
SFO1 300.1324010 MHz
SI 32768SF 300.1300219 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0PC 1.00
30405060708090100110120130140150160170180 ppm
34
.92
40
.19
51
.74
55
.26
67
.27
68
.16
71
.20
71
.91
73
.50
76
.72
77
.15
77
.57
77
.89
79
.05
81
.84
11
3.9
61
27
.52
12
7.6
51
27
.69
12
7.7
91
28
.23
12
8.4
11
29
.05
13
2.8
51
37
.60
13
8.3
2
13
8.4
2
15
8.4
5
17
4.5
9
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S20
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 1.0 0.5 0.0 ppm
2.5
53
2.5
87
2.6
07
2.7
87
2.8
15
2.8
69
3.3
03
3.3
18
3.3
34
3.4
26
3.4
41
3.5
95
3.6
18
3.6
34
3.6
58
3.6
72
3.6
87
3.7
02
3.7
61
3.7
90
3.8
72
3.8
89
3.9
20
4.0
37
4.5
03
4.5
18
4.5
37
4.5
52
5.3
51
6.1
02
6.1
13
6.2
68
6.2
74
6.2
78
6.2
85
7.0
48
7.0
66
7.0
73
7.2
25
7.2
41
7.2
49
7.2
63
7.2
70
7.2
86
7.2
94
7.3
03
7.3
11
7.3
13
7.3
23
7.3
32
7.3
37
1.0
1
1.0
2
1.0
61
.06
2.9
51
.09
1.0
31
.09
2.0
21
.99
4.2
4
0.9
5
1.0
3
1.0
0
2.0
8
14
.67
2030405060708090100110120130140150160170180 ppm
33
.28
35
.42
51
.89
67
.35
67
.94
71
.36
71
.87
73
.54
75
.73
76
.73
77
.15
77
.58
79
.20
81
.85
10
6.1
21
10
.33
12
7.5
11
27
.64
12
7.6
81
27
.71
12
7.7
51
27
.82
12
8.3
41
28
.41
12
8.4
51
37
.78
13
8.3
61
38
.43
14
1.6
5
15
4.9
9
17
4.3
3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S21
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 1.0 0.5 0.0 ppm
-0.0
00
1.6
15
1.6
36
2.1
95
2.2
15
2.2
46
2.2
67
2.4
71
2.4
97
2.5
23
2.5
49
2.9
57
2.9
74
2.9
91
3.3
65
3.3
79
3.3
94
3.5
35
3.5
53
3.5
83
3.6
80
3.6
95
3.7
10
3.7
68
3.7
97
3.8
26
3.9
03
3.9
21
4.2
74
4.3
12
4.3
61
4.3
99
4.5
11
4.5
17
4.5
26
4.5
59
4.5
61
5.3
29
5.3
42
5.3
97
5.4
01
5.4
74
5.4
95
7.2
34
7.2
50
7.2
56
7.2
67
7.2
77
7.2
95
7.3
19
7.3
34
3.1
1
1.1
3
0.9
6
1.0
20
.88
1.1
20
.97
3.0
01
.05
1.0
21
.00
2.2
2
3.9
9
0.9
00
.89
1.0
1
15
.00
2030405060708090100110120130140150160170180 ppm
18
.21
35
.38
39
.26
51
.68
67
.53
68
.39
71
.53
71
.93
73
.57
75
.89
76
.75
77
.18
77
.60
79
.14
82
.05
12
6.5
51
27
.61
12
7.7
21
27
.87
12
7.9
01
28
.46
12
8.4
81
28
.51
13
0.7
81
37
.86
13
8.3
71
38
.45
17
4.7
5
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S22
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.834
2.865
2.887
2.918
3.199
3.216
3.233
3.386
3.400
3.415
3.430
3.520
3.535
3.586
3.648
3.663
3.678
3.692
3.766
3.790
3.804
3.819
3.832
3.847
3.864
3.900
4.504
4.519
4.540
5.412
6.817
6.827
7.187
7.197
7.208
7.215
7.243
7.272
7.289
7.303
7.335
7.349
1.0
6
1.1
3
1.0
0
1.0
0
1.0
1
2.8
9
1.1
5
5.3
5
4.1
5
0.8
8
1.9
9
19
.37
NAME xwy-591EXPNO 10
PROCNO 1Date_ 20120608
Time 20.11
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 8DS 0
SWH 8992.806 Hz
FIDRES 0.137219 Hz
AQ 3.6438515 sec
RG 181
DW 55.600 usecDE 8.00 usec
TE 299.4 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.30 usecPL1 3.00 dB
SFO1 300.1324010 MHz
SI 32768SF 300.1300105 MHz
WDW EMSSB 0
LB 0.30 Hz
GB 0PC 1.00
405060708090100110120130140150160170180 ppm
34
.70
41
.00
51
.84
67
.34
68
.03
71
.21
71
.98
73
.57
76
.74
77
.16
77
.58
77
.98
79
.17
81
.95
12
6.8
4
12
7.5
5
12
7.6
9
12
7.7
2
12
7.7
8
12
7.8
6
12
8.1
9
12
8.2
9
12
8.4
7
12
8.4
8
12
8.6
4
13
7.6
3
13
8.4
0
13
8.5
5
14
1.0
3
17
4.6
8
NAME xwy-591EXPNO 21
PROCNO 1Date_ 20120608
Time 23.38
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30TD 65536
SOLVENT CDCl3
NS 270DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 574.7DW 27.800 usec
DE 6.50 usec
TE 299.7 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 13C
P1 12.50 usec
PL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1HPCPD2 100.00 usec
PL2 3.00 dB
PL12 22.74 dBPL13 23.00 dB
SFO2 300.1312005 MHzSI 32768
SF 75.4677392 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S23
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.8
08
2.8
38
2.8
61
2.8
91
3.1
51
3.1
68
3.1
84
3.3
78
3.3
93
3.4
07
3.4
23
3.5
01
3.5
17
3.5
51
3.5
80
3.6
47
3.6
62
3.6
77
3.6
91
3.7
50
3.7
88
3.8
22
3.8
50
3.8
61
3.9
35
3.9
72
4.5
05
4.5
19
4.5
34
5.2
77
6.8
00
6.8
29
6.8
51
6.8
62
7.1
22
7.1
50
7.1
94
7.2
03
7.2
15
7.2
35
7.2
63
7.2
73
7.2
89
7.3
28
1.0
6
1.0
2
1.0
0
1.1
0
1.0
2
2.9
7
1.1
0
3.9
3
3.0
6
1.0
0
3.9
1
0.9
3
4.0
1
15
.00
NAME xwy-639EXPNO 10
PROCNO 1
Date_ 20120611
Time 17.18
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 0SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 90.5
DW 55.600 usecDE 8.00 usec
TE 299.8 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 10.30 usec
PL1 3.00 dBSFO1 300.1324010 MHz
SI 32768SF 300.1300132 MHz
WDW EM
SSB 0LB 0.30 Hz
GB 0
PC 1.00
2030405060708090100110120130140150160170180 ppm
34
.97
40
.26
51
.80
55
.33
67
.43
68
.08
71
.25
71
.95
73
.56
76
.74
77
.16
77
.58
77
.88
79
.13
82
.03
11
4.0
01
27
.54
12
7.6
91
27
.73
12
7.8
41
28
.27
12
8.4
41
28
.47
12
9.0
81
33
.01
13
7.6
71
38
.40
13
8.5
5
15
8.4
9
17
4.6
8
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S24
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.4
62
2.4
71
2.5
11
2.5
20
3.0
26
3.0
58
3.0
75
3.1
07
3.2
62
3.3
72
3.4
21
3.6
69
3.7
66
3.7
82
3.8
84
3.8
90
3.9
02
3.9
32
4.2
88
4.3
12
4.4
25
4.5
80
4.6
20
4.6
32
4.6
73
4.6
96
4.7
17
4.7
37
4.7
57
7.0
29
7.0
40
7.1
99
7.2
08
7.2
21
7.2
46
7.2
53
7.2
63
7.2
77
7.2
89
7.3
09
7.3
34
0.9
5
1.0
0
0.9
3
0.9
8
0.9
5
4.9
7
2.9
3
1.1
3
4.0
4
5.2
4
20
.75
NAME xwy-599-0914EXPNO 10
PROCNO 1
Date_ 20120915
Time 10.13
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 10
DS 0SWH 8992.806 Hz
FIDRES 0.137219 Hz
AQ 3.6438515 secRG 71.8
DW 55.600 usec
DE 8.00 usec
TE 299.6 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 10.30 usec
PL1 3.00 dBSFO1 300.1324010 MHz
SI 32768
SF 300.1300173 MHzWDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
30405060708090100110120130140150160170180 ppm
36.03
42.33
52.42
71.55
72.30
72.50
73.37
73.71
76.02
76.74
77.16
77.36
77.58
78.21
127.06
127.65
127.70
127.74
127.80
127.90
127.92
127.95
128.36
128.38
128.46
128.81
137.38
138.40
138.42
138.78
143.24
174.94
NAME xwy-599-0914EXPNO 11
PROCNO 1Date_ 20120915
Time 10.16
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 396DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 3649.1
DW 27.800 usecDE 6.50 usec
TE 300.0 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 12.50 usec
PL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
PCPD2 100.00 usecPL2 3.00 dB
PL12 22.74 dBPL13 23.00 dB
SFO2 300.1312005 MHz
SI 32768SF 75.4677434 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S25
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
88
2.5
97
2.6
44
2.6
53
3.0
36
3.0
65
3.0
92
3.1
22
3.3
05
3.3
19
3.3
28
3.3
42
3.3
63
3.3
83
3.4
05
3.6
64
3.6
79
3.7
05
3.7
19
3.7
99
3.8
04
4.0
24
4.0
61
4.1
12
4.1
27
4.1
34
4.1
42
4.1
49
4.1
58
4.1
82
4.2
06
4.2
47
4.2
71
4.2
85
4.3
09
4.3
39
4.3
78
7.1
09
7.1
14
7.1
20
7.1
34
7.1
96
7.2
16
7.2
24
7.2
36
7.2
39
7.2
60
7.2
80
7.2
87
7.3
03
7.3
12
1.0
5
1.0
0
1.9
4
1.0
2
0.9
9
0.9
81
.97
1.9
61
.01
4.0
3
11
.50
405060708090100110120130140150160170180 ppm
40
.30
40
.54
46
.39
68
.52
71
.62
72
.28
76
.73
77
.16
77
.58
81
.84
84
.64
12
7.3
6
12
7.7
9
12
7.8
5
12
7.9
5
12
8.4
1
12
8.4
7
12
8.8
2
13
7.3
1
13
7.6
4
14
0.1
1
17
4.4
1
NAME xwy-570EXPNO 11
PROCNO 1Date_ 20120418
Time 17.25
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 38DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 2896.3
DW 27.800 usecDE 6.50 usec
TE 295.9 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 12.50 usec
PL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
PCPD2 100.00 usecPL2 3.00 dB
PL12 22.33 dBPL13 23.00 dB
SFO2 300.1312005 MHz
SI 32768SF 75.4677515 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S26
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
19
2.5
28
2.5
76
2.5
84
3.0
13
3.0
42
3.0
69
3.0
99
3.3
25
3.3
39
3.3
48
3.3
61
3.3
75
3.3
97
3.6
61
3.6
75
3.7
05
3.7
20
3.7
60
3.7
68
4.0
95
4.1
24
4.1
32
4.1
46
4.1
70
4.2
44
4.2
83
4.3
12
4.3
49
4.3
88
6.7
39
6.7
62
6.7
68
6.9
99
7.0
28
7.1
34
7.1
39
7.1
58
7.1
65
7.2
04
7.2
25
7.2
30
7.2
62
7.2
77
7.2
83
0.9
8
1.0
0
2.0
1
5.1
4
3.0
81
.07
2.1
1
2.0
7
2.1
5
2.0
6
8.4
8
30405060708090100110120130140150160170180 ppm
39
.87
40
.56
46
.30
55
.14
68
.69
71
.51
72
.16
76
.73
77
.16
77
.58
81
.69
84
.67
11
4.0
31
27
.72
12
7.7
51
27
.77
12
7.8
41
28
.33
12
8.3
91
28
.87
13
2.1
21
37
.32
13
7.6
3
15
8.6
3
17
4.2
9
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S27
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
59
2.5
70
2.6
15
2.6
26
2.9
18
2.9
47
3.3
73
3.3
82
3.3
97
3.4
05
3.4
21
3.6
25
3.6
41
3.6
66
3.6
81
3.8
39
3.8
49
4.0
53
4.0
77
4.1
01
4.1
53
4.1
59
4.1
68
4.1
75
4.2
93
4.3
31
4.3
41
4.3
81
4.4
12
4.4
29
4.4
52
4.4
67
6.1
12
6.1
23
6.2
58
6.2
64
6.2
68
6.2
74
7.2
32
7.2
52
7.2
58
7.2
70
7.2
75
7.2
84
7.2
90
7.2
97
7.3
03
7.3
21
7.3
29
7.3
41
7.3
49
1.0
0
1.0
0
1.9
8
1.0
3
1.0
0
0.9
91
.03
2.0
32
.00
0.9
6
0.9
7
10
.99
30405060708090100110120130140150160170180 ppm
34
.84
38
.13
46
.31
67
.75
71
.74
72
.59
76
.72
77
.15
77
.57
82
.55
84
.51
10
7.1
7
11
0.4
5
12
7.7
51
27
.82
12
7.8
91
28
.36
12
8.4
31
37
.37
13
7.7
41
42
.03
15
3.5
7
17
3.8
9
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S28
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 1.0 0.5 0.0 ppm
1.5
73
1.5
93
2.1
33
2.1
41
2.1
88
2.1
96
2.7
75
2.8
02
2.8
30
2.8
57
3.0
83
3.1
09
3.2
56
3.2
75
3.2
97
3.3
17
3.7
56
3.7
67
3.7
98
3.8
08
3.9
32
3.9
36
3.9
51
3.9
70
4.1
53
4.1
64
4.1
72
4.1
83
4.4
31
4.4
70
4.4
77
4.5
13
4.5
17
4.5
42
4.5
81
5.3
05
5.3
09
5.3
38
5.3
55
5.3
59
5.3
89
5.4
19
5.4
39
5.4
60
5.4
90
5.5
10
7.2
90
7.3
12
7.3
22
7.3
40
7.3
68
3.1
8
1.0
0
1.0
5
1.0
2
1.0
0
1.0
5
2.0
3
1.0
4
3.9
5
1.0
3
1.0
3
10
.04
2030405060708090100110120130140150160170180 ppm
17
.80
39
.02
40
.06
46
.32
68
.35
71
.48
72
.00
76
.72
77
.15
77
.57
81
.70
84
.25
12
7.4
91
27
.70
12
7.7
71
27
.79
12
7.8
91
28
.43
12
8.4
61
29
.57
13
7.4
11
37
.66
17
4.4
4
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S29
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 1.0 0.5 0.0 ppm
2.5
75
2.5
84
2.6
32
2.6
41
3.0
26
3.0
56
3.3
57
3.3
75
3.3
84
3.4
02
3.5
75
3.5
89
3.6
68
3.6
87
3.7
65
3.8
76
3.9
13
4.0
67
4.0
83
4.1
78
4.2
15
4.2
23
4.2
50
4.2
58
4.2
75
4.2
90
4.3
29
4.3
68
4.4
25
4.4
65
4.5
06
4.5
42
4.5
82
7.0
37
7.0
42
7.0
49
7.0
59
7.0
67
7.1
41
7.1
48
7.1
63
7.1
84
7.2
38
7.2
45
7.2
55
7.2
62
7.2
69
7.2
73
7.2
87
7.3
03
7.3
15
0.9
8
1.0
0
1.0
3
1.0
3
2.0
2
1.0
4
1.0
2
3.0
5
4.1
7
2.1
44
.41
13
.97
30405060708090100110120130140150160170180 ppm
40
.24
40
.26
58
.86
67
.44
69
.00
72
.19
72
.30
73
.28
76
.75
77
.17
77
.60
83
.02
87
.74
12
7.3
81
27
.73
12
7.8
01
27
.93
12
7.9
81
28
.32
12
8.3
61
28
.41
12
8.8
51
37
.65
13
7.7
5
13
7.9
31
40
.10
17
3.9
7
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S30
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 1.0 0.5 0.0 ppm
2.5
88
2.5
96
3.3
70
3.3
87
3.3
97
3.4
14
3.5
83
3.5
96
3.6
69
3.6
88
3.7
01
3.7
21
3.7
52
3.9
61
3.9
99
4.0
58
4.0
75
4.2
03
4.2
28
4.2
54
4.2
66
4.2
81
4.2
97
4.3
42
4.3
81
4.4
42
4.4
79
4.5
18
4.5
53
4.5
93
6.7
94
6.8
23
7.0
47
7.0
76
7.0
87
7.0
95
7.1
03
7.1
59
7.1
65
7.1
80
7.1
90
7.2
24
7.2
46
7.2
54
7.2
60
7.2
69
7.2
72
7.2
92
7.3
03
7.3
13
7.3
24
1.0
0
1.0
0
1.0
1
1.0
05
.15
1.0
91
.08
3.2
11
.12
1.3
52
.01
2.1
6
4.3
12
.16
11
.28
2030405060708090100110120130140150160170180 ppm
39
.73
40
.63
55
.27
58
.87
67
.73
69
.02
72
.24
72
.34
73
.33
76
.72
77
.14
77
.57
83
.02
87
.86
11
4.1
91
27
.76
12
7.8
31
27
.96
12
8.3
61
28
.40
12
8.4
51
28
.99
13
2.2
01
37
.73
13
7.8
41
37
.99
15
8.7
9
17
4.0
3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S31
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
70
2.5
81
2.6
26
2.6
37
2.9
27
2.9
57
2.9
83
3.0
14
3.4
38
3.4
56
3.4
65
3.4
83
3.5
30
3.5
43
3.5
63
3.5
75
3.6
62
3.6
80
3.6
95
3.7
13
3.8
33
4.0
26
4.0
41
4.1
36
4.1
62
4.1
87
4.2
04
4.2
42
4.2
83
4.3
00
4.3
16
4.3
74
4.4
12
4.4
51
4.4
59
4.4
84
4.5
00
4.5
23
4.5
37
4.5
77
4.6
67
6.1
51
6.1
61
6.2
89
6.2
96
6.3
05
7.1
90
7.2
08
7.2
15
7.2
28
7.2
50
7.2
63
7.2
87
7.3
03
7.3
35
7.3
43
7.3
53
1.00
1.00
1.00
1.03
1.05
1.06
1.04
2.06
1.08
1.26
4.35
1.04
1.02
17.08
2030405060708090100110120130140150160170180 ppm
34
.69
38
.21
58
.99
66
.94
69
.20
72
.44
72
.77
73
.40
76
.74
77
.16
77
.58
83
.83
87
.75
10
7.3
2
11
0.5
6
12
7.7
91
27
.87
12
8.0
21
28
.42
12
8.4
51
28
.48
13
7.8
61
38
.05
14
2.1
8
15
3.6
5
17
3.5
6
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S32
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 1.0 0.5 ppm
1.6
15
1.6
35
2.1
55
2.1
65
2.2
11
2.2
21
2.7
54
2.7
81
2.8
09
2.8
37
3.5
37
3.5
52
3.5
70
3.5
84
3.6
05
3.6
26
3.6
37
3.6
58
3.9
08
3.9
23
3.9
33
3.9
49
3.9
86
4.0
09
4.0
34
4.0
82
4.1
00
4.2
93
4.3
07
4.3
21
4.4
51
4.4
78
4.4
89
4.5
17
4.5
38
4.5
61
4.5
78
4.6
01
5.4
01
5.4
05
5.4
33
5.4
72
5.4
92
7.2
51
7.2
56
7.2
71
7.2
80
7.2
93
7.3
07
7.3
21
7.3
24
3.1
6
1.0
5
1.0
7
1.0
0
2.2
9
1.0
11
.06
1.1
0
1.1
0
6.7
1
2.2
4
15
.93
2030405060708090100110120130140150160170180 ppm
17
.96
38
.52
39
.70
58
.95
67
.26
69
.12
72
.18
72
.27
73
.35
76
.74
77
.17
77
.59
82
.88
87
.70
12
7.7
11
27
.77
12
7.8
41
27
.90
12
8.0
41
28
.48
12
9.2
91
37
.84
13
7.9
41
38
.06
17
4.1
7
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S33
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.4
29
2.4
85
2.8
94
2.9
08
2.9
21
2.9
35
3.0
20
3.0
49
3.0
76
3.1
04
3.6
09
3.6
35
3.6
57
3.6
84
3.7
12
3.7
67
3.8
04
3.8
76
3.8
90
3.9
05
3.9
27
3.9
56
3.9
77
3.9
91
4.0
05
4.0
42
4.3
75
4.4
01
4.4
26
4.4
52
4.4
57
4.4
67
6.9
90
6.9
95
7.0
06
7.0
13
7.0
21
7.0
36
7.1
47
7.1
53
7.1
73
7.1
89
7.2
06
7.2
12
7.2
21
7.2
32
1.0
0
1.0
2
1.0
1
2.0
0
1.0
2
4.0
0
1.2
0
3.9
9
3.9
3
16
.28
NAME xwy-614EXPNO 10
PROCNO 1
Date_ 20120524
Time 9.59
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 9
DS 0SWH 8992.806 Hz
FIDRES 0.137219 Hz
AQ 3.6438515 secRG 64
DW 55.600 usecDE 8.00 usec
TE 299.5 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.30 usec
PL1 3.00 dBSFO1 300.1324010 MHz
SI 32768
SF 300.1300404 MHz
WDW EM
SSB 0
LB 0.30 HzGB 0
PC 1.00
30405060708090100110120130140150160170180 ppm
41
.15
41
.47
56
.96
66
.28
67
.01
72
.36
73
.33
73
.87
76
.72
77
.15
77
.57
79
.06
79
.23
12
7.4
61
27
.68
12
7.7
01
27
.80
12
7.9
11
27
.96
12
8.3
71
28
.42
12
8.4
51
28
.86
13
7.4
71
38
.16
13
8.2
31
40
.58
17
5.6
3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S34
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.4
44
2.4
99
3.0
01
3.0
15
3.0
27
3.0
41
3.0
64
3.0
92
3.1
19
3.1
47
3.6
19
3.6
44
3.6
70
3.7
36
3.7
59
3.7
93
3.9
14
3.9
52
3.9
59
3.9
74
3.9
85
4.0
04
4.0
33
4.0
45
4.0
62
4.0
73
4.1
50
4.1
87
4.4
08
4.4
33
4.4
57
4.5
33
4.5
51
6.7
82
6.8
11
6.9
66
6.9
95
7.1
06
7.1
12
7.1
28
7.1
38
7.2
07
7.2
29
7.2
51
7.2
58
7.2
67
7.2
73
7.2
84
7.2
95
7.3
00
7.3
11
0.9
9
0.9
8
1.0
0
1.0
2
4.0
0
4.1
1
1.0
7
1.0
9
3.9
7
1.9
8
2.0
7
2.0
4
13
.31
NAME xwy-588EXPNO 10
PROCNO 1Date_ 20120503
Time 15.03
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 8
DS 0SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 35.9
DW 55.600 usecDE 8.00 usec
TE 298.2 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 10.30 usecPL1 3.00 dB
SFO1 300.1324010 MHz
SI 32768SF 300.1300217 MHz
WDW EM
SSB 0LB 0.30 Hz
GB 0
PC 1.00
30405060708090100110120130140150160170180 ppm
40
.46
41
.58
55
.26
56
.82
66
.25
67
.19
72
.27
73
.24
73
.74
76
.75
77
.17
77
.60
78
.85
79
.13
11
4.0
91
27
.61
12
7.6
51
27
.74
12
7.8
51
27
.88
12
8.3
01
28
.36
12
8.3
81
28
.69
13
2.4
81
37
.47
13
8.0
91
38
.19
15
8.7
8
17
5.6
3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S35
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.4
72
2.4
77
2.5
27
2.5
31
2.9
89
3.0
18
3.0
43
3.0
72
3.1
48
3.1
62
3.1
72
3.1
87
3.7
35
3.7
64
3.7
93
3.9
49
3.9
69
3.9
79
3.9
91
3.9
99
4.0
06
4.0
21
4.0
85
4.1
03
4.1
13
4.1
30
4.1
81
4.2
19
4.3
18
4.3
36
4.3
58
4.3
83
4.5
38
4.5
67
4.5
85
4.6
23
6.0
99
6.1
10
6.2
75
6.2
81
6.2
86
6.2
92
7.2
02
7.2
07
7.2
24
7.2
33
7.2
54
7.2
76
7.2
81
7.2
97
7.3
06
7.3
17
7.3
54
1.0
6
1.0
8
1.0
3
2.1
3
2.1
3
1.1
1
1.0
5
2.1
4
2.2
2
2.2
6
1.0
0
0.9
9
16
.40
NAME xwy-594p1EXPNO 10
PROCNO 1Date_ 20120505
Time 14.57
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 16DS 0
SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 181
DW 55.600 usecDE 8.00 usec
TE 298.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.30 usecPL1 3.00 dB
SFO1 300.1324010 MHzSI 32768
SF 300.1300092 MHz
WDW EMSSB 0
LB 0.30 Hz
GB 0PC 1.00
30405060708090100110120130140150160170180 ppm
35
.77
39
.57
57
.00
66
.50
66
.88
72
.88
73
.34
73
.89
76
.74
77
.16
77
.58
79
.42
10
7.1
5
11
0.5
1
12
7.7
21
27
.78
12
7.9
11
27
.99
12
8.0
61
28
.43
12
8.4
71
28
.51
13
7.6
91
38
.23
13
8.3
21
42
.14
15
4.3
0
17
5.1
8
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S36
2.02.53.03.54.04.55.05.56.06.57.07.5 ppm
1.5
91
1.6
10
2.1
24
2.1
28
2.1
79
2.1
83
2.7
98
2.8
24
2.8
52
2.8
78
3.0
07
3.0
32
3.0
58
3.6
58
3.6
72
3.6
83
3.6
97
3.7
33
3.7
63
3.7
90
3.9
08
3.9
25
3.9
38
3.9
57
4.1
07
4.1
33
4.1
44
4.1
57
4.1
73
4.1
81
4.2
05
4.2
28
4.3
57
4.3
96
4.5
21
4.5
39
4.5
59
4.6
59
4.6
68
5.1
95
5.1
99
5.2
24
5.2
28
5.2
46
5.2
50
5.2
74
5.2
79
5.4
63
5.4
84
5.5
14
5.5
35
7.2
46
7.2
68
7.2
77
7.2
95
7.3
12
2.9
2
1.0
2
0.9
7
0.9
4
0.9
9
1.1
7
1.1
2
2.9
4
1.0
8
3.0
0
2.1
7
1.1
4
1.0
0
15
.34
405060708090100110120130140150160170180 ppm
38
.49
40
.35
56
.63
66
.30
66
.51
72
.29
73
.29
73
.85
76
.70
77
.12
77
.54
78
.07
79
.36
12
7.6
7
12
7.7
8
12
7.8
8
12
7.9
1
12
7.9
7
12
8.0
2
12
8.4
1
12
8.5
1
12
8.6
3
13
7.6
5
13
8.2
0
13
8.2
5
17
5.4
5
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S37
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
58
2.6
15
3.0
13
3.0
42
3.4
66
3.4
93
3.5
18
3.6
60
3.6
86
3.7
35
3.7
40
3.7
67
3.7
72
3.9
29
3.9
48
4.0
19
4.0
56
4.0
77
4.1
03
4.1
39
4.1
56
4.1
71
4.1
91
4.2
17
4.2
41
4.3
58
4.3
96
4.4
14
4.4
53
4.4
77
4.4
84
4.5
15
4.5
30
4.5
69
7.0
16
7.0
39
7.0
64
7.0
93
7.1
17
7.1
28
7.1
52
7.1
76
7.2
07
7.2
32
7.2
39
7.2
55
7.2
69
7.2
77
7.2
91
7.3
01
7.3
21
0.9
5
1.0
0
0.9
8
0.9
9
1.0
4
1.0
4
1.9
7
2.1
5
1.2
3
4.0
0
20
.43
30405060708090100110120130140150160170180 ppm
40
.58
41
.94
55
.30
64
.01
66
.24
72
.56
73
.06
73
.19
76
.72
77
.15
77
.57
79
.14
85
.81
12
7.1
01
27
.39
12
7.6
61
27
.68
12
7.7
11
27
.87
12
8.2
21
28
.32
13
7.6
81
38
.04
13
8.3
21
40
.23
17
2.7
1
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S38
3.03.54.04.55.05.56.06.57.07.5 ppm
2.576
2.604
3.105
3.587
3.599
3.612
3.677
3.690
3.715
3.825
3.828
3.841
3.844
3.999
4.100
4.113
4.126
4.161
4.180
4.244
4.253
4.260
4.269
4.283
4.295
4.308
4.436
4.455
4.519
4.538
4.557
4.572
4.591
4.609
4.629
6.596
6.611
7.124
7.138
7.223
7.235
7.252
7.259
7.265
7.300
7.311
7.317
7.322
7.330
7.344
7.349
7.361
7.373
0.9
9
1.0
0
1.0
3
1.0
3
2.9
8
1.0
2
1.0
0
1.0
1
1.0
1
1.0
2
1.0
1
1.0
1
4.0
6
1.9
7
2.0
7
2.0
1
2.3
7
10
.99
NAME nOEEXPNO 65PROCNO 1
Date_ 20120427Time 15.10
INSTRUM spectPROBHD 5 mm BBI 1H-BB
PULPROG zg30TD 65536
SOLVENT CDCl3NS 8
DS 0SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219786 sec
RG 11.3DW 27.800 usec
DE 6.50 usecTE 298.0 K
D1 2.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 11.80 usecPL1 2.00 dB
PL1W 15.84893227 WSFO1 600.1328788 MHz
SI 65536SF 600.1300218 MHz
WDW EMSSB 0
LB 0.30 HzGB 0
PC 1.00
30405060708090100110120130140150160170180 ppm
39
.92
42
.31
55
.15
55
.28
64
.16
66
.41
72
.53
73
.05
73
.25
76
.72
77
.15
77
.57
79
.11
85
.84
11
3.6
21
27
.40
12
7.6
11
27
.67
12
7.9
11
28
.22
12
8.3
11
28
.34
12
9.3
11
32
.37
13
7.7
61
38
.07
13
8.3
6
15
8.5
4
17
2.7
2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S39
ppm
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
NAME xwy-571EXPNO 11PROCNO 1Date_ 20120419
Time 15.23INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG cosygpqfTD 2048
SOLVENT CDCl3
NS 1DS 8SWH 1680.108 Hz
FIDRES 0.820365 Hz
AQ 0.6095348 secRG 22.6DW 297.600 usec
DE 8.00 usecTE 295.6 K
D0 0.00000300 sec
D1 1.18624496 secD13 0.00000400 sec
D16 0.00020000 sec
IN0 0.00059520 sec
======== CHANNEL f1 ========
NUC1 1H
P0 10.80 usecP1 10.80 usec
PL1 3.00 dBSFO1 300.1315011 MHz
====== GRADIENT CHANNEL =====
GPNAM1 SINE.100GPZ1 10.00 %
P16 1000.00 usec
ND0 1TD 83SFO1 300.1315 MHz
FIDRES 20.242260 HzSW 5.598 ppmFnMODE QF
SI 1024SF 300.1300244 MHzWDW SINESSB 0
LB 0.00 HzGB 0PC 1.40
SI 1024MC2 QFSF 300.1300244 MHz
WDW SINE
SSB 0LB 0.00 Hz
GB 0
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S40
NOESY experiment and molecular model from Chem3D of 9db
ppm
3.63.73.83.94.04.14.24.34.4 ppm
3.6
3.7
3.8
3.9
4.0
4.1
4.2
4.3
4.4
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S41
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
59
2.6
14
2.9
39
2.9
67
2.9
95
3.0
23
3.5
45
3.5
71
3.5
96
3.7
42
3.7
72
3.7
91
3.7
99
3.9
50
3.9
73
3.9
95
4.0
01
4.0
21
4.2
21
4.2
45
4.2
69
4.4
17
4.4
34
4.4
56
4.4
72
4.4
78
4.5
17
4.5
52
4.5
74
4.6
15
4.6
88
6.0
82
6.0
93
6.0
99
6.1
05
6.1
16
7.1
71
7.1
73
7.2
07
7.2
14
7.2
28
7.2
39
7.2
47
7.2
67
7.2
89
7.2
98
7.3
19
7.3
27
7.3
42
7.3
52
7.3
71
0.9
9
1.0
1
1.0
0
1.9
5
2.9
0
1.0
3
3.1
3
3.0
8
1.9
4
16
.43
30405060708090100110120130140150160170180 ppm
35
.76
40
.19
55
.29
64
.35
66
.07
73
.10
73
.26
73
.30
76
.72
77
.14
77
.56
79
.83
85
.65
10
7.5
21
10
.51
12
7.4
51
27
.81
12
7.9
01
28
.30
12
8.4
71
37
.93
13
8.3
11
38
.53
14
1.6
2
15
3.8
1
17
2.3
2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S42
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
1.2
62
1.2
79
2.0
85
2.1
39
2.8
00
2.8
54
2.9
36
2.9
57
3.6
53
3.6
57
3.6
85
3.6
89
3.8
07
3.8
27
3.8
33
3.8
53
3.8
66
3.8
85
4.1
69
4.1
95
4.2
21
4.2
50
4.2
65
4.2
74
4.2
84
4.2
98
4.4
95
4.5
10
4.5
46
4.5
63
4.6
03
4.6
17
4.6
57
4.7
15
4.7
54
5.3
75
5.3
94
5.4
08
5.4
36
7.2
22
7.2
33
7.2
39
7.2
49
7.2
56
7.2
72
7.2
76
7.2
87
7.3
00
7.3
11
7.3
23
7.3
28
2.6
3
0.4
6
0.9
6
1.0
0
0.8
9
1.0
0
1.9
7
3.0
0
2.0
5
1.9
5
1.0
2
1.0
2
1.9
1
15
.00
NAME xwy-568EXPNO 10
PROCNO 1Date_ 20120417
Time 9.17
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 14
DS 0
SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 40.3
DW 55.600 usecDE 8.00 usec
TE 295.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.80 usecPL1 3.00 dB
SFO1 300.1324010 MHz
SI 32768SF 300.1300172 MHz
WDW EMSSB 0
LB 0.30 Hz
GB 0PC 1.00
30405060708090100110120130140150160170180 ppm
17
.46
41
.13
42
.16
55
.00
64
.00
66
.25
72
.22
73
.18
73
.48
76
.71
77
.14
77
.56
79
.00
85
.15
12
7.2
7
12
7.4
5
12
7.5
1
12
7.5
8
12
7.6
6
12
7.7
4
12
7.9
7
12
8.2
6
12
8.3
6
12
8.4
2
13
0.0
4
13
8.0
7
13
8.3
3
13
8.4
0
17
2.7
8
NAME xwy-568EXPNO 11
PROCNO 1Date_ 20120417
Time 9.21
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 71DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 1024
DW 27.800 usecDE 6.50 usec
TE 295.7 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 12.50 usec
PL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
PCPD2 100.00 usecPL2 3.00 dB
PL12 22.33 dBPL13 23.00 dB
SFO2 300.1312005 MHz
SI 32768SF 75.4677516 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S43
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 1.0 0.5 0.0 ppm
-0.0
02
2.5
78
2.6
35
3.0
41
3.0
70
3.4
70
3.4
96
3.5
21
3.6
69
3.6
95
3.7
22
3.7
46
3.7
51
3.7
78
3.7
83
3.9
43
3.9
63
4.0
22
4.0
59
4.0
77
4.1
03
4.1
31
4.1
49
4.1
64
4.1
81
4.2
06
4.2
31
4.2
55
4.3
61
4.3
98
4.4
30
4.4
54
4.4
69
4.4
93
4.5
36
4.5
76
7.0
32
7.0
54
7.0
79
7.1
09
7.1
32
7.1
58
7.1
67
7.1
77
7.2
45
7.2
54
7.2
68
7.2
75
7.2
88
7.3
12
7.3
31
1.0
5
1.0
0
1.1
01
.06
1.0
41
.04
1.8
11
.26
1.0
91
.02
4.3
1
2.0
47
.18
11
.71
2030405060708090100110120130140150160170180 ppm
40
.75
42
.10
55
.52
64
.19
66
.49
72
.73
73
.24
73
.36
76
.72
77
.14
77
.56
79
.35
85
.99
12
7.2
51
27
.53
12
7.8
11
27
.86
12
8.0
11
28
.36
12
8.4
71
37
.84
13
8.1
91
38
.48
14
0.3
7
17
2.8
9
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S44
2.53.03.54.04.55.05.56.06.57.07.5 ppm
2.5
15
2.5
18
2.5
72
2.5
75
3.5
35
3.5
37
3.5
62
3.6
46
3.6
81
3.7
58
3.7
64
3.7
90
3.7
96
4.0
49
4.0
75
4.0
85
4.1
00
4.1
23
4.1
58
4.1
75
4.1
90
4.2
22
4.2
47
4.2
71
4.3
71
4.4
08
4.4
67
4.4
95
4.5
07
4.5
19
4.5
46
4.5
85
6.5
37
6.5
66
7.0
59
7.0
88
7.1
52
7.1
57
7.1
75
7.1
82
7.2
02
7.2
14
7.2
52
7.2
56
7.2
64
7.2
69
7.2
73
7.2
84
7.2
90
7.3
14
7.3
31
1.0
1
1.0
5
1.0
0
0.9
0
2.9
3
1.0
4
1.0
7
1.9
9
1.0
4
1.1
0
1.0
0
3.9
5
1.8
7
1.9
4
15
.53
NAME xwy-640-0806EXPNO 10
PROCNO 1Date_ 20120806
Time 17.44
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536SOLVENT CDCl3
NS 16
DS 0SWH 8992.806 Hz
FIDRES 0.137219 HzAQ 3.6438515 sec
RG 322.5
DW 55.600 usecDE 8.00 usec
TE 301.1 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 10.30 usecPL1 3.00 dB
SFO1 300.1324010 MHz
SI 32768SF 300.1300087 MHz
WDW EM
SSB 0LB 0.30 Hz
GB 0
PC 1.00
405060708090100110120130140150160170180 ppm
40
.12
42
.48
55
.35
55
.54
64
.36
66
.69
72
.73
73
.26
73
.44
76
.74
77
.16
77
.58
79
.35
86
.05
11
3.8
4
12
7.5
7
12
7.8
0
12
7.8
4
12
8.0
8
12
8.3
9
12
8.4
8
12
8.5
1
12
9.4
9
13
2.5
6
13
7.9
5
13
8.2
5
13
8.5
5
15
8.7
6
17
2.9
4
NAME xwy-640-0806EXPNO 13
PROCNO 1Date_ 20120807
Time 8.38
INSTRUM spectPROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 979DS 4
SWH 17985.611 Hz
FIDRES 0.274439 HzAQ 1.8219508 sec
RG 645.1
DW 27.800 usecDE 6.50 usec
TE 300.6 KD1 2.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 12.50 usec
PL1 2.00 dBSFO1 75.4752953 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
PCPD2 100.00 usecPL2 3.00 dB
PL12 22.74 dBPL13 23.00 dB
SFO2 300.1312005 MHz
SI 32768SF 75.4677387 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
S45
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 1.0 0.5 0.0 ppm
2.4
96
2.6
12
2.6
42
2.9
95
3.6
69
3.6
81
3.8
47
3.8
58
3.8
63
3.8
73
3.8
85
3.9
84
4.0
02
4.0
09
4.3
52
4.3
92
4.4
82
4.5
22
4.5
69
4.6
00
4.6
09
4.6
41
4.6
87
4.7
26
4.7
77
4.8
19
7.0
03
7.0
08
7.0
27
7.0
34
7.0
53
7.0
66
7.0
77
7.0
84
7.1
93
7.2
02
7.2
12
7.2
15
7.2
25
7.2
34
7.2
61
7.2
73
7.2
83
7.2
92
7.3
15
7.3
36
7.3
43
7.3
52
7.4
23
7.4
45
7.4
50
1.0
0
0.9
8
1.9
4
1.0
0
1.9
81
.97
1.0
21
.04
1.0
02
.02
3.0
50
.97
3.9
0
19
.13
1.9
1
2030405060708090100110120130140150160170180 ppm
38
.77
39
.63
42
.22
66
.47
71
.78
72
.21
73
.73
73
.82
73
.98
75
.76
76
.72
77
.14
77
.57
79
.03
79
.76
12
7.0
41
27
.24
12
7.4
61
27
.55
12
7.6
21
27
.68
12
7.7
11
27
.85
12
7.9
91
28
.12
12
8.3
11
28
.36
12
8.4
41
28
.60
12
8.9
01
37
.71
13
8.6
81
38
.83
13
8.9
11
40
.85
17
3.3
9
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
