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Supporting Information
First Stereoselective Total Synthesis of Neosemburin and
Isoneosemburin
Gadi Madhusudhan Reddy and Perali Ramu Sridhar
School of Chemistry, University of Hyderabad, 500 046
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2014
2
Contents
1) Copies of 1H, 13C, DEPT Spectra of compound 15………………………………………S3 - S5
2) Copies of 1H, 13C, DEPT Spectra of compound 16………………………………………S6 - S8
3) Copies of 1H, 13C, DEPT Spectra of compound 17………………………………………S9 - S11
4) Copies of 1H, 13C, DEPT Spectra of compound 18……………………………………..S12 - S14
5) Copies of 1H, 13C, DEPT Spectra of compound 19……………………………………..S15 - S17
6) Copies of 1H, 13C, DEPT Spectra of compound 20…………………………….………S18 - S20
7) Copies of 1H, 13C, DEPT, COSY, NOESY Spectra of compound 21…………….……S21 - S28
8) Copies of 1H, 13C, DEPT Spectra of compound 24……………………………………..S29 - S31
9) Copies of 1H, 13C, DEPT Spectra of compound 25…………………………………….S32 - S34
10) Copies of 1H, 13C, DEPT Spectra of compound 26……………………………….…..S35 - S37
11) Copies of 1H, 13C, DEPT, COSY, NOESY Spectra of compound 28……….………..S38 - S42
12) Copies of 1H, 13C, DEPT Spectra of compound 22……………………………….…..S43 - S45
13) Copies of 1H, 13C, DEPT, COSY, NOESY Spectra of compound 3…………………..S46 - S53
14) Table of comparitative spectral data for isolated and ..... S54
synthesised neosemburin (3)
S3
9 8 7 6 5 4 3 2 1 ppm
6.0
7
9.1
4
1.0
1
1.0
9
3.0
6
1.0
7
2.0
2
2.0
9
1.0
3
1.0
3
1.0
0
NAME madhu500EXPNO 205210PROCNO 20521Date_ 20140328Time 16.18INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536
SOLVENT CDCl3NS 16DS 2SWH 10330.578 Hz
FIDRES 0.157632 HzAQ 3.1719923 secRG 40.3DW 48.400 usecDE 6.50 usecTE 296.4 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.90 usec
PL1 2.00 dBPL1W 12.85348415 WSFO1 500.1830888 MHz
SI 32768SF 500.1800000 MHzWDW EMSSB 0
LB 0.30 HzGB 0PC 1.00
S4
200 180 160 140 120 100 80 60 40 20 ppm
-5.39
18.25
21.18
25.88
32.33
38.00
60.07
63.95
70.15
76.68
77.00
102.23
143.06
170.55
NAME madhu(PRS)
EXPNO 205212PROCNO 1
Date_ 20140328Time 15.38INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 1848DS 4
SWH 30120.482 HzFIDRES 0.459602 HzAQ 1.0879476 secRG 20642.5DW 16.600 usecDE 6.00 usecTE 297.1 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
PCPD2 80.00 usecPL2 0.00 dB
PL12 18.06 dB
PL13 14.00 dBSFO2 400.1316005 MHzSI 32768SF 100.6127704 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S5
200 180 160 140 120 100 80 60 40 20 ppm
-5.36
21.21
25.90
32.36
38.02
60.09
63.97
70.17
102.25
143.07
NAME madhu(PRS)
EXPNO 205213PROCNO 1
Date_ 20140328Time 14.01INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG dept135TD 65536SOLVENT CDCl3NS 417DS 4
SWH 23980.814 HzFIDRES 0.365918 HzAQ 1.3664756 secRG 16384DW 20.850 usecDE 6.00 usecTE 296.9 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 secd12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
P3 14.40 usecp4 28.80 usecPCPD2 80.00 usecPL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127690 MHzWDW EMSSB 0
LB 1.00 HzGB 0
PC 1.40
S6
10 9 8 7 6 5 4 3 2 1 0 ppm
5.8
0
9.1
2
1.1
0
1.0
1
0.9
9
2.0
2
1.0
2
1.0
0
1.0
0
1.0
5
1.0
0
NAME madhu(PRS)EXPNO 205221PROCNO 1Date_ 20121224Time 16.15INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8012.820 Hz
FIDRES 0.122266 HzAQ 4.0894966 secRG 28.5DW 62.400 usecDE 6.00 usecTE 291.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.00 usec
PL1 0.00 dBSFO1 400.1318754 MHzSI 32768SF 400.1300069 MHzWDW EMSSB 0
LB 0.30 HzGB 0PC 1.00
S7
200 180 160 140 120 100 80 60 40 20 0 ppm
-5.55
-5.45
18.22
25.78
39.01
40.18
62.44
68.14
68.51
76.68
77.00
77.31
103.36
143.01
NAME madhu(PRS)
EXPNO 205222PROCNO 1Date_ 20121224Time 16.19INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 187DS 4
SWH 30120.482 Hz
FIDRES 0.459602 HzAQ 1.0879476 secRG 1824.6DW 16.600 usecDE 6.00 usecTE 291.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 80.00 usecPL2 0.00 dBPL12 18.06 dB
PL13 14.00 dB
SFO2 400.1316005 MHzSI 32768
SF 100.6127732 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S8
200 180 160 140 120 100 80 60 40 20 0 ppm
-5.55
-5.45
25.78
39.01
40.18
68.13
68.50
103.36
143.01
NAME madhu(PRS)
EXPNO 205223PROCNO 1Date_ 20121224Time 16.31INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG dept135TD 65536SOLVENT CDCl3NS 82DS 4
SWH 23980.814 Hz
FIDRES 0.365918 HzAQ 1.3664756 secRG 16384DW 20.850 usecDE 6.00 usecTE 292.0 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 sec
d12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.40 usec
p4 28.80 usecPCPD2 80.00 usec
PL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127733 MHzWDW EMSSB 0LB 1.00 HzGB 0
PC 1.40
S9
10 9 8 7 6 5 4 3 2 1 0 ppm
6.08
9.05
2.03
1.09
2.08
1.81
1.14
1.00
NAME madhu(PRS)
EXPNO 205231PROCNO 1Date_ 20121225Time 16.14INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zg30TD 65536
SOLVENT CDCl3NS 16DS 2
SWH 8012.820 HzFIDRES 0.122266 HzAQ 4.0894966 secRG 14.3DW 62.400 usec
DE 6.00 usecTE 291.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 10.00 usecPL1 0.00 dB
SFO1 400.1318754 MHzSI 32768SF 400.1300096 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S10
200 180 160 140 120 100 80 60 40 20 ppm
18.17
25.79
31.84
61.05
65.12
72.10
76.68
77.00
77.32
134.52
144.45
194.73 NAME madhu(PRS)
EXPNO 205232PROCNO 1Date_ 20121225Time 16.18INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 148DS 4
SWH 30120.482 Hz
FIDRES 0.459602 HzAQ 1.0879476 secRG 1290.2DW 16.600 usecDE 6.00 usecTE 292.1 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 80.00 usecPL2 0.00 dBPL12 18.06 dB
PL13 14.00 dB
SFO2 400.1316005 MHzSI 32768
SF 100.6127759 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S11
200 180 160 140 120 100 80 60 40 20 0 ppm
-5.47
25.76
57.99
65.09
72.07
144.42
NAME madhu(PRS)
EXPNO 205233PROCNO 1Date_ 20121225Time 16.26INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG dept135TD 65536SOLVENT CDCl3NS 38DS 4
SWH 23980.814 Hz
FIDRES 0.365918 HzAQ 1.3664756 secRG 16384DW 20.850 usecDE 6.00 usecTE 292.1 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 sec
d12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.40 usec
p4 28.80 usecPCPD2 80.00 usec
PL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127792 MHzWDW EMSSB 0LB 1.00 HzGB 0
PC 1.40
S12
10 9 8 7 6 5 4 3 2 1 0 ppm
0.9
7
2.0
1
0.9
7
1.0
3
1.0
1
0.9
8
0.9
9
0.9
9
1.0
0
NAME madhu(PRS)EXPNO 213011
PROCNO 1Date_ 20131220Time 14.01
INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8012.820 Hz
FIDRES 0.122266 HzAQ 4.0894966 secRG 45.3DW 62.400 usecDE 6.00 usecTE 294.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.00 usec
PL1 0.00 dBSFO1 400.1318754 MHzSI 32768SF 400.1300098 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S13
200 180 160 140 120 100 80 60 40 20 ppm
61.05
64.74
76.68
77.00
77.32
91.81
92.34
126.99
129.92
149.07 NAME madhu(PRS)
EXPNO 213012PROCNO 1Date_ 20131220Time 14.08INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 50DS 4
SWH 30120.482 Hz
FIDRES 0.459602 HzAQ 1.0879476 secRG 20642.5DW 16.600 usecDE 6.00 usecTE 294.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 80.00 usecPL2 0.00 dBPL12 14.00 dB
PL13 14.00 dB
SFO2 400.1316005 MHzSI 32768
SF 100.6127749 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S14
200 180 160 140 120 100 80 60 40 20 0 ppm
61.05
64.74
91.81
92.34
126.99
129.93
149.07
NAME madhu(PRS)
EXPNO 213013PROCNO 1Date_ 20131220Time 14.03INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG dept135TD 65536SOLVENT CDCl3NS 21DS 4
SWH 23980.814 Hz
FIDRES 0.365918 HzAQ 1.3664756 secRG 16384DW 20.850 usecDE 6.00 usecTE 294.6 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 sec
d12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.40 usec
p4 28.80 usecPCPD2 80.00 usec
PL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127747 MHzWDW EMSSB 0LB 1.00 HzGB 0
PC 1.40
S15
10 9 8 7 6 5 4 3 2 1 0 ppm3.4
0
2.2
8
1.0
0
0.8
2
1.1
3
0.9
8
1.0
9
1.0
6
1.0
4NAME madhu400 opeEXPNO 213531
PROCNO 2093Date_ 20120214Time 13.04
INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 Hz
FIDRES 0.125483 HzAQ 3.9846387 secRG 80.6DW 60.800 usecDE 6.50 usecTE 295.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.80 usec
PL1 1.50 dBPL1W 15.18650627 WSFO1 400.0934707 MHzSI 32768SF 400.0910095 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S16
200 180 160 140 120 100 80 60 40 20 ppm
12.73
33.35
50.52
61.63
76.68
77.00
77.32
103.59
122.60
132.59
144.40
201.44 NAME madhu400 ope
EXPNO 213532PROCNO 2093Date_ 20120214Time 13.09INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 60DS 4
SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.50 usecTE 296.6 KD1 2.00000000 secD11 0.03000000 secTD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 10.00 usecPL1 2.00 dBPL1W 49.44866943 WSFO1 100.6130223 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 1.50 dBPL12 17.18 dB
PL13 20.18 dB
PL2W 15.18650627 WPL12W 0.41063678 W
PL13W 0.20580591 WSFO2 400.0926004 MHzSI 32768SF 100.6029683 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
S17
200 180 160 140 120 100 80 60 40 20 0 ppm
12.73
33.35
50.53
61.63
103.60
122.61
144.40
201.44
NAME madhu400 ope
EXPNO 213533PROCNO 2093Date_ 20120214Time 13.12INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG dept135TD 65536SOLVENT CDCl3NS 28DS 4
SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 2050DW 20.800 usecDE 6.50 usecTE 296.3 KCNST2 145.0000000D1 2.00000000 secD2 0.00344828 sec
D12 0.00002000 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 10.00 usecP2 20.00 usecPL1 2.00 dBPL1W 49.44866943 W
SFO1 100.6130223 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.80 usec
P4 29.60 usecPCPD2 90.00 usec
PL2 1.50 dBPL12 17.18 dBPL2W 15.18650627 WPL12W 0.41063678 WSFO2 400.0926004 MHzSI 32768SF 100.6029681 MHzWDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
S18
10 9 8 7 6 5 4 3 2 1 0 ppm
1.0
1
3.2
2
0.8
6
1.1
4
0.9
4
2.0
1
0.9
9
0.7
5
0.8
4
1.0
3
0.9
9
NAME madhu400 opeEXPNO 213711
PROCNO 2093Date_ 20120214Time 17.04
INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 Hz
FIDRES 0.125483 HzAQ 3.9846387 secRG 57DW 60.800 usecDE 6.50 usecTE 295.4 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.80 usec
PL1 1.50 dBPL1W 15.18650627 WSFO1 400.0934707 MHzSI 32768SF 400.0910093 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S19
200 180 160 140 120 100 80 60 40 20 ppm
12.70
35.63
39.76
60.19
61.24
76.68
77.00
77.32
104.88
121.79
133.61
143.40 NAME madhu400 ope
EXPNO 213712PROCNO 2093Date_ 20120214Time 17.07INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 68DS 4
SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 575DW 20.800 usecDE 6.50 usecTE 296.5 KD1 2.00000000 secD11 0.03000000 secTD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 10.00 usecPL1 2.00 dBPL1W 49.44866943 WSFO1 100.6130223 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 1.50 dBPL12 17.18 dB
PL13 20.18 dB
PL2W 15.18650627 WPL12W 0.41063678 W
PL13W 0.20580591 WSFO2 400.0926004 MHzSI 32768SF 100.6029705 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
S20
200 180 160 140 120 100 80 60 40 20 0 ppm
12.70
35.62
39.76
60.19
61.24
104.88
121.79
143.40
NAME madhu400 ope
EXPNO 213713PROCNO 2093Date_ 20120214Time 17.12INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG dept135TD 65536SOLVENT CDCl3NS 60DS 4
SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 2050DW 20.800 usecDE 6.50 usecTE 296.1 KCNST2 145.0000000D1 2.00000000 secD2 0.00344828 sec
D12 0.00002000 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 10.00 usecP2 20.00 usecPL1 2.00 dBPL1W 49.44866943 W
SFO1 100.6130223 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.80 usec
P4 29.60 usecPCPD2 90.00 usec
PL2 1.50 dBPL12 17.18 dBPL2W 15.18650627 WPL12W 0.41063678 WSFO2 400.0926004 MHzSI 32768SF 100.6029706 MHzWDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
S21
10 9 8 7 6 5 4 3 2 1 0 ppm
1.1
2
3.0
8
1.8
8
1.0
8
0.9
9
1.0
8
2.2
5
1.0
0
0.9
9
0.9
6
NAME madhu400 opeEXPNO 213731
PROCNO 2093Date_ 20120214Time 21.18
INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT C6D6NS 16DS 2SWH 8223.685 Hz
FIDRES 0.125483 HzAQ 3.9846387 secRG 64DW 60.800 usecDE 6.50 usecTE 295.6 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.80 usec
PL1 1.50 dBPL1W 15.18650627 WSFO1 400.0934707 MHzSI 32768SF 400.0909957 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S22
200 180 160 140 120 100 80 60 40 20 ppm
12.18
29.66
30.61
34.67
57.21
62.00
92.83
118.79
127.57
127.81
128.05
139.17 NAME madhu(PRS)
EXPNO 213732PROCNO 1Date_ 20131214Time 20.21INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT C6D6NS 205DS 4
SWH 30120.482 Hz
FIDRES 0.459602 HzAQ 1.0879476 secRG 3251DW 16.600 usecDE 6.00 usecTE 294.6 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 80.00 usecPL2 0.00 dBPL12 14.00 dB
PL13 14.00 dB
SFO2 400.1316005 MHzSI 32768
SF 100.6127690 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S23
200 180 160 140 120 100 80 60 40 20 0 ppm
12.19
29.67
30.63
34.68
57.22
62.01
92.84
118.79
NAME madhu(PRS)
EXPNO 213733PROCNO 1Date_ 20131214Time 20.29INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG dept135TD 65536SOLVENT C6D6NS 156DS 4
SWH 23980.814 Hz
FIDRES 0.365918 HzAQ 1.3664756 secRG 26008DW 20.850 usecDE 6.00 usecTE 294.7 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 sec
d12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.40 usec
p4 28.80 usecPCPD2 80.00 usec
PL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127678 MHzWDW EMSSB 0LB 1.00 HzGB 0
PC 1.40
S24
10 9 8 7 6 5 4 3 2 1 0 ppm
1.1
7
3.4
6
2.6
3
1.2
3
1.0
6
1.1
2
1.1
8
1.0
2
1.0
2
1.3
1
0.8
3
NAME madhu(PRS)EXPNO 213721
PROCNO 1Date_ 20131214Time 19.44
INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8012.820 Hz
FIDRES 0.122266 HzAQ 4.0894966 secRG 28.5DW 62.400 usecDE 6.00 usecTE 294.4 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.00 usec
PL1 0.00 dBSFO1 400.1318754 MHzSI 32768SF 400.1300096 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S25
200 180 160 140 120 100 80 60 40 20 ppm
12.52
29.45
29.97
34.47
57.40
62.36
76.68
77.00
77.32
92.93
119.59
138.21 NAME madhu(PRS)
EXPNO 213722PROCNO 1Date_ 20131214Time 19.46INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 65DS 4
SWH 30120.482 Hz
FIDRES 0.459602 HzAQ 1.0879476 secRG 2048DW 16.600 usecDE 6.00 usecTE 294.6 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 80.00 usecPL2 0.00 dBPL12 18.06 dB
PL13 14.00 dB
SFO2 400.1316005 MHzSI 32768
SF 100.6127758 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S26
200 180 160 140 120 100 80 60 40 20 0 ppm
12.60
29.52
30.04
34.55
57.47
62.44
93.00
119.66
NAME madhu(PRS)
EXPNO 213723PROCNO 1Date_ 20131214Time 19.51INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG dept135TD 65536SOLVENT CDCl3NS 43DS 4
SWH 23980.814 Hz
FIDRES 0.365918 HzAQ 1.3664756 secRG 16384DW 20.850 usecDE 6.00 usecTE 294.8 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 sec
d12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.40 usec
p4 28.80 usecPCPD2 80.00 usec
PL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127690 MHzWDW EMSSB 0LB 1.00 HzGB 0
PC 1.40
S27
ppm
1.52.02.53.03.54.04.55.05.56.0 ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
NAME madhu400 ope
EXPNO 213734
PROCNO 2093Date_ 20120214
Time 21.23INSTRUM spectPROBHD 5 mm PABBO BB-
PULPROG cosygpqf
TD 2048SOLVENT C6D6
NS 1DS 8SWH 1920.123 HzFIDRES 0.937560 Hz
AQ 0.5333492 secRG 36DW 260.400 usec
DE 6.50 usecTE 295.6 K
D0 0.00000300 sec
D1 1.48689198 secD13 0.00000400 secD16 0.00020000 sec
IN0 0.00052070 sec
======== CHANNEL f1 ========
NUC1 1H
P0 14.80 usecP1 14.80 usec
PL1 1.50 dB
PL1W 15.18650627 WSFO1 400.0923190 MHz
====== GRADIENT CHANNEL =====GPNAM1 SINE.100
GPZ1 10.00 %
P16 1000.00 usecND0 1TD 128
SFO1 400.0923 MHz
FIDRES 15.003462 HzSW 4.800 ppmFnMODE QF
SI 1024SF 400.0910000 MHzWDW SINE
SSB 0LB 0.00 HzGB 0PC 1.00
SI 1024
MC2 QFSF 400.0910000 MHz
WDW SINESSB 0LB 0.00 Hz
GB 0
S28
ppm
1.52.02.53.03.54.04.55.05.56.0 ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
NAME madhu400 ope
EXPNO 213735
PROCNO 2093Date_ 20120214Time 21.34INSTRUM spectPROBHD 5 mm PABBO BB-
PULPROG noesygpphTD 2048SOLVENT C6D6NS 32
DS 4SWH 2160.760 Hz
FIDRES 1.055059 Hz
AQ 0.4739572 secRG 114
DW 231.400 usecDE 6.50 usecTE 295.5 KD0 0.00021258 secD1 2.00000000 sec
D8 0.69999999 secD16 0.00020000 secIN0 0.00046285 sec
======== CHANNEL f1 ========
NUC1 1H
P1 14.80 usecP2 29.60 usecPL1 1.50 dB
PL1W 15.18650627 W
SFO1 400.0923250 MHz
====== GRADIENT CHANNEL =====GPNAM1 SINE.100
GPNAM2 SINE.100GPZ1 80.00 %GPZ2 40.00 %P16 1000.00 usecND0 1
TD 256
SFO1 400.0923 MHzFIDRES 8.439447 HzSW 5.400 ppm
FnMODE States-TPPISI 1024SF 400.0910000 MHzWDW QSINESSB 2LB 0.00 HzGB 0PC 1.00
SI 1024
MC2 States-TPPISF 400.0910000 MHzWDW QSINESSB 2LB 0.00 HzGB 0
S29
10 9 8 7 6 5 4 3 2 1 ppm
2.1
4
1.1
6
1.0
6
2.8
0
2.8
1
1.1
3
2.9
2
0.9
7
1.0
0
2.1
7
0.9
6
1.2
2
NAME madhu(PRS)EXPNO 205623
PROCNO 1Date_ 20130115Time 11.50
INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8012.820 Hz
FIDRES 0.122266 HzAQ 4.0894966 secRG 28.5DW 62.400 usecDE 6.00 usecTE 292.4 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.00 usec
PL1 0.00 dBSFO1 400.1318754 MHzSI 32768SF 400.1300098 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S30
200 180 160 140 120 100 80 60 40 20 ppm
20.97
30.94
31.64
34.42
54.68
59.87
61.91
71.76
76.68
77.00
77.32
97.09
170.47
171.01
NAME madhu(PRS)
EXPNO 205624PROCNO 1Date_ 20130115Time 12.01INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 114DS 4SWH 30120.482 Hz
FIDRES 0.459602 HzAQ 1.0879476 secRG 20642.5DW 16.600 usecDE 6.00 usecTE 292.7 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 80.00 usecPL2 0.00 dBPL12 18.06 dBPL13 14.00 dB
SFO2 400.1316005 MHzSI 32768
SF 100.6127738 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S31
200 180 160 140 120 100 80 60 40 20 ppm
20.93
30.90
31.60
34.38
54.64
59.83
61.87
71.72
97.06
NAME madhu(PRS)
EXPNO 205625PROCNO 1Date_ 20130115Time 13.58INSTRUM AV400PROBHD 5 mm PABBO BB/
PULPROG dept135TD 65536SOLVENT CDCl3NS 38DS 4
SWH 23980.814 HzFIDRES 0.365918 HzAQ 1.3664756 sec
RG 16384DW 20.850 usecDE 6.00 usecTE 293.0 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 secd12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
P3 14.40 usecp4 28.80 usecPCPD2 80.00 usecPL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127777 MHzWDW EMSSB 0LB 1.00 Hz
GB 0
PC 1.40
S32
10 9 8 7 6 5 4 3 2 1 ppm
6.0
4
8.9
8
2.8
0
1.0
6
1.0
1
3.2
4
1.0
3
2.0
4
1.0
2
1.0
1
1.0
0
NAME madhu(PRS)EXPNO 205731
PROCNO 1Date_ 20130129Time 15.50
INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8012.820 Hz
FIDRES 0.122266 HzAQ 4.0894966 secRG 35.9DW 62.400 usecDE 6.00 usecTE 294.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.00 usec
PL1 0.00 dBSFO1 400.1318754 MHzSI 32768SF 400.1300069 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S33
200 180 160 140 120 100 80 60 40 20 0 ppm
-5.56
-5.49
18.24
25.82
36.35
37.99
38.50
54.47
62.73
63.12
70.59
76.71
77.03
77.34
97.21 NAME madhu(PRS)
EXPNO 205732PROCNO 1Date_ 20130129Time 15.53INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 100DS 4SWH 30120.482 Hz
FIDRES 0.459602 HzAQ 1.0879476 secRG 1149.4DW 16.600 usecDE 6.00 usecTE 294.8 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 80.00 usecPL2 0.00 dBPL12 18.06 dBPL13 14.00 dB
SFO2 400.1316005 MHzSI 32768
SF 100.6127690 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S34
200 180 160 140 120 100 80 60 40 20 0 ppm
-5.56
-5.49
25.82
36.36
37.99
38.50
54.47
62.73
63.12
70.59
97.21
NAME madhu(PRS)
EXPNO 205733PROCNO 1Date_ 20130129Time 15.59INSTRUM AV400PROBHD 5 mm PABBO BB/
PULPROG dept135TD 65536SOLVENT CDCl3NS 64DS 4
SWH 23980.814 HzFIDRES 0.365918 HzAQ 1.3664756 sec
RG 16384DW 20.850 usecDE 6.00 usecTE 294.9 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 secd12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
P3 14.40 usecp4 28.80 usecPCPD2 80.00 usecPL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127690 MHzWDW EMSSB 0LB 1.00 Hz
GB 0
PC 1.40
S35
10 9 8 7 6 5 4 3 2 1 ppm
12.3
4
18.2
0
3.6
3
1.0
8
2.2
0
0.9
9
1.1
4
1.1
6
1.0
0
2.9
3
2.8
6
4.1
4
2.0
0
1.2
0
0.8
8
0.9
6
1.0
0
NAME madhu(PRS)
EXPNO 206111PROCNO 1Date_ 20130129
Time 15.21INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2
SWH 8012.820 Hz
FIDRES 0.122266 HzAQ 4.0894966 secRG 7.1DW 62.400 usecDE 6.00 usecTE 294.5 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.00 usec
PL1 0.00 dBSFO1 400.1318754 MHzSI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 HzGB 0
PC 1.00
S36
200 180 160 140 120 100 80 60 40 20 0 ppm
-5.43
18.21
25.87
30.56
31.66
33.22
35.23
39.29
39.73
55.25
55.29
60.35
66.39
67.38
76.74
77.06
77.38
97.50
98.75
208.63
212.41
NAME madhu(PRS)
EXPNO 206112PROCNO 1Date_ 20130129Time 15.24INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 103DS 4SWH 30120.482 Hz
FIDRES 0.459602 HzAQ 1.0879476 secRG 20642.5DW 16.600 usecDE 6.00 usecTE 294.6 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 80.00 usecPL2 0.00 dBPL12 18.06 dBPL13 14.00 dB
SFO2 400.1316005 MHzSI 32768
SF 100.6127690 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S37
200 180 160 140 120 100 80 60 40 20 0 ppm
-5.44
-5.41
25.86
25.88
30.56
31.66
31.89
33.22
35.23
39.29
39.73
55.25
55.29
60.34
66.39
67.38
97.50
98.75
NAME madhu(PRS)
EXPNO 206113PROCNO 1Date_ 20130129Time 15.33INSTRUM AV400PROBHD 5 mm PABBO BB/
PULPROG dept135TD 65536SOLVENT CDCl3NS 64DS 4
SWH 23980.814 HzFIDRES 0.365918 HzAQ 1.3664756 sec
RG 16384DW 20.850 usecDE 6.00 usecTE 294.9 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 secd12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
P3 14.40 usecp4 28.80 usecPCPD2 80.00 usecPL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127690 MHzWDW EMSSB 0LB 1.00 Hz
GB 0
PC 1.40
S38
10 9 8 7 6 5 4 3 2 1 ppm
0.9
9
0.9
4
0.9
5
2.0
0
3.0
8
1.0
1
1.0
4
2.1
3
1.0
0
NAME madhu400 opeEXPNO 206321
PROCNO 1Date_ 20130202Time 1.50
INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 Hz
FIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.50 usecTE 296.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.80 usec
PL1 1.50 dBPL1W 15.18650627 WSFO1 400.0934707 MHzSI 32768SF 400.0910084 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S39
200 180 160 140 120 100 80 60 40 20 ppm29.48
32.20
36.91
54.90
61.98
66.31
76.72
77.04
77.35
97.25
100.89
NAME madhu (prs)
EXPNO 206322PROCNO 1Date_ 20130201Time 21.27INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 120DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 575DW 20.800 usecDE 6.50 usecTE 296.8 KD1 2.00000000 secD11 0.03000000 secTD0 1
======== CHANNEL f1 ========NUC1 13C
P1 10.00 usecPL1 2.00 dBPL1W 49.44866943 WSFO1 100.6130223 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 1.50 dBPL12 17.18 dBPL13 20.18 dB
PL2W 15.18650627 WPL12W 0.41063678 W
PL13W 0.20580591 WSFO2 400.0926004 MHzSI 32768SF 100.6029620 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
S40
200 180 160 140 120 100 80 60 40 20 ppm
29.48
32.20
36.91
54.91
61.97
66.31
97.25
NAME madhu (prs)
EXPNO 206323PROCNO 1Date_ 20130201Time 21.33INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG dept135TD 65536SOLVENT CDCl3NS 92DS 4
SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 2050DW 20.800 usecDE 6.50 usecTE 296.3 KCNST2 145.0000000
D1 2.00000000 secD2 0.00344828 secD12 0.00002000 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 10.00 usecP2 20.00 usec
PL1 2.00 dBPL1W 49.44866943 WSFO1 100.6130223 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.80 usec
P4 29.60 usecPCPD2 90.00 usecPL2 1.50 dBPL12 17.18 dBPL2W 15.18650627 WPL12W 0.41063678 WSFO2 400.0926004 MHzSI 32768SF 100.6029620 MHzWDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
S41
ppm
1.52.02.53.03.54.04.55.0 ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
NAME madhu (prs)
EXPNO 213814
PROCNO 2093Date_ 20120215
Time 20.51INSTRUM spectPROBHD 5 mm PABBO BB-
PULPROG cosygpqf
TD 2048SOLVENT CDCl3
NS 1DS 8SWH 1640.420 HzFIDRES 0.800986 Hz
AQ 0.6242804 secRG 144DW 304.800 usec
DE 6.50 usecTE 295.6 K
D0 0.00000300 sec
D1 1.48689198 secD13 0.00000400 secD16 0.00020000 sec
IN0 0.00060960 sec
======== CHANNEL f1 ========
NUC1 1H
P0 14.80 usecP1 14.80 usec
PL1 1.50 dB
PL1W 15.18650627 WSFO1 400.0921890 MHz
====== GRADIENT CHANNEL =====GPNAM1 SINE.100
GPZ1 10.00 %
P16 1000.00 usecND0 1TD 128
SFO1 400.0922 MHz
FIDRES 12.815453 HzSW 4.100 ppmFnMODE QF
SI 1024SF 400.0910000 MHzWDW SINE
SSB 0LB 0.00 HzGB 0PC 1.00
SI 1024
MC2 QFSF 400.0910000 MHz
WDW SINESSB 0LB 0.00 Hz
GB 0
S42
ppm
1.52.02.53.03.54.04.55.0 ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
NAME madhu400 ope
EXPNO 213815
PROCNO 2093Date_ 20120215Time 21.02INSTRUM spectPROBHD 5 mm PABBO BB-
PULPROG noesygpphTD 2048SOLVENT CDCl3NS 32
DS 4SWH 4084.967 Hz
FIDRES 1.994613 Hz
AQ 0.2507252 secRG 812
DW 122.400 usecDE 6.50 usecTE 295.5 KD0 0.00010357 secD1 2.00000000 sec
D8 0.69999999 secD16 0.00020000 secIN0 0.00024480 sec
======== CHANNEL f1 ========
NUC1 1H
P1 14.80 usecP2 29.60 usecPL1 1.50 dB
PL1W 15.18650627 W
SFO1 400.0928417 MHz
====== GRADIENT CHANNEL =====GPNAM1 SINE.100
GPNAM2 SINE.100GPZ1 80.00 %GPZ2 40.00 %P16 1000.00 usecND0 1
TD 256
SFO1 400.0928 MHzFIDRES 15.955348 HzSW 10.209 ppm
FnMODE States-TPPISI 1024SF 400.0910000 MHzWDW QSINESSB 2LB 0.00 HzGB 0PC 1.00
SI 1024
MC2 States-TPPISF 400.0910000 MHzWDW QSINESSB 2LB 0.00 HzGB 0
S43
10 9 8 7 6 5 4 3 2 1 ppm
0.8
0
3.3
5
2.6
5
2.4
2
0.9
7
2.8
7
2.2
0
1.0
5
1.1
2
1.0
3
1.0
0
NAME madhu(PRS)EXPNO 206511
PROCNO 1Date_ 20130206Time 23.30
INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8012.820 Hz
FIDRES 0.122266 HzAQ 4.0894966 secRG 28.5DW 62.400 usecDE 6.00 usecTE 293.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.00 usec
PL1 0.00 dBSFO1 400.1318754 MHzSI 32768SF 400.1300069 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S44
200 180 160 140 120 100 80 60 40 20 ppm
12.77
29.61
35.90
55.97
60.93
67.59
76.73
77.05
77.37
99.59
120.86
135.94
NAME madhu(PRS)
EXPNO 206512PROCNO 1Date_ 20130206Time 23.35INSTRUM AV400PROBHD 5 mm PABBO BB/PULPROG zgpg30TD 65536SOLVENT CDCl3NS 84DS 4SWH 30120.482 Hz
FIDRES 0.459602 HzAQ 1.0879476 secRG 1149.4DW 16.600 usecDE 6.00 usecTE 293.2 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13CP1 11.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 80.00 usecPL2 0.00 dBPL12 18.06 dBPL13 14.00 dB
SFO2 400.1316005 MHzSI 32768
SF 100.6127690 MHzWDW EMSSB 0LB 3.00 HzGB 0PC 1.40
S45
200 180 160 140 120 100 80 60 40 20 ppm
12.77
29.61
35.86
35.91
55.97
60.93
67.59
99.59
120.86
NAME madhu(PRS)
EXPNO 206513PROCNO 1Date_ 20130206Time 23.40INSTRUM AV400PROBHD 5 mm PABBO BB/
PULPROG dept135TD 65536SOLVENT CDCl3NS 64DS 4
SWH 23980.814 HzFIDRES 0.365918 HzAQ 1.3664756 sec
RG 16384DW 20.850 usecDE 6.00 usecTE 293.2 KCNST2 145.0000000D1 2.00000000 secd2 0.00344828 secd12 0.00002000 secDELTA 0.00001401 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 11.00 usecp2 22.00 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16
NUC2 1H
P3 14.40 usecp4 28.80 usecPCPD2 80.00 usecPL2 -2.50 dBPL12 12.27 dBSFO2 400.1316005 MHzSI 32768SF 100.6127690 MHzWDW EMSSB 0LB 1.00 Hz
GB 0
PC 1.40
S46
10 9 8 7 6 5 4 3 2 1 0 ppm
1.2
7
3.6
3
2.0
2
1.4
1
0.1
1
1.0
0
1.1
7
2.0
9
1.2
4
1.0
7
1.1
2
NAME madhu400 opeEXPNO 214011
PROCNO 2093Date_ 20131217Time 19.11
INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT C6D6NS 16DS 2SWH 8223.685 Hz
FIDRES 0.125483 HzAQ 3.9846387 secRG 114DW 60.800 usecDE 6.50 usecTE 295.3 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.80 usec
PL1 1.50 dBPL1W 15.18650627 WSFO1 400.0934707 MHzSI 32768SF 400.0909955 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S47
200 180 160 140 120 100 80 60 40 20 ppm
12.50
26.37
29.28
31.76
57.07
67.34
93.50
118.65
127.82
127.95
128.06
128.30
139.54 NAME madhu400 ope
EXPNO 214012PROCNO 2093Date_ 20131217Time 19.19INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT C6D6NS 256DS 4
SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 456DW 20.800 usecDE 6.50 usecTE 296.1 KD1 2.00000000 secD11 0.03000000 secTD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 10.00 usecPL1 2.00 dBPL1W 49.44866943 WSFO1 100.6130223 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 1.50 dBPL12 17.18 dB
PL13 20.18 dB
PL2W 15.18650627 WPL12W 0.41063678 W
PL13W 0.20580591 WSFO2 400.0926004 MHzSI 32768SF 100.6029234 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
S48
200 180 160 140 120 100 80 60 40 20 0 ppm
12.50
26.37
29.28
31.76
57.07
67.34
93.50
118.66
NAME madhu400 ope
EXPNO 214013PROCNO 2093Date_ 20131217Time 19.31INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG dept135TD 65536SOLVENT C6D6NS 64DS 4
SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 2050DW 20.800 usecDE 6.50 usecTE 296.5 KCNST2 145.0000000D1 2.00000000 secD2 0.00344828 sec
D12 0.00002000 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 10.00 usecP2 20.00 usecPL1 2.00 dBPL1W 49.44866943 W
SFO1 100.6130223 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.80 usec
P4 29.60 usecPCPD2 90.00 usec
PL2 1.50 dBPL12 17.18 dBPL2W 15.18650627 WPL12W 0.41063678 WSFO2 400.0926004 MHzSI 32768SF 100.6029237 MHzWDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
S49
10 9 8 7 6 5 4 3 2 1 ppm
0.9
4
3.4
6
0.9
5
0.8
8
1.2
6
1.0
5
1.1
9
1.2
1
1.0
4
1.0
9
1.1
2
1.0
0
NAME madhu400 opeEXPNO 206521
PROCNO 1Date_ 20130207Time 22.57
INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 Hz
FIDRES 0.125483 HzAQ 3.9846387 secRG 128DW 60.800 usecDE 6.50 usecTE 295.9 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.80 usec
PL1 1.50 dBPL1W 15.18650627 WSFO1 400.0934707 MHzSI 32768SF 400.0910000 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S50
200 180 160 140 120 100 80 60 40 20 ppm
12.62
25.81
28.99
31.34
57.11
67.46
76.71
77.03
77.34
93.40
119.37
138.43
NAME madhu (prs)
EXPNO 206522PROCNO 1Date_ 20130207Time 18.31INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zgpg30TD 65536SOLVENT CDCl3NS 160DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.50 usecTE 296.7 KD1 2.00000000 secD11 0.03000000 secTD0 1
======== CHANNEL f1 ========NUC1 13C
P1 10.00 usecPL1 2.00 dBPL1W 49.44866943 WSFO1 100.6130223 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 1.50 dBPL12 17.18 dBPL13 20.18 dB
PL2W 15.18650627 WPL12W 0.41063678 W
PL13W 0.20580591 WSFO2 400.0926004 MHzSI 32768SF 100.6029620 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
S51
200 180 160 140 120 100 80 60 40 20 ppm
12.62
25.80
28.98
31.33
57.10
67.46
93.39
119.37
NAME madhu400 ope
EXPNO 206523PROCNO 1Date_ 20130207Time 23.11INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG dept135TD 65536SOLVENT CDCl3NS 80DS 4
SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631988 secRG 2050DW 20.800 usecDE 6.50 usecTE 296.9 KCNST2 145.0000000
D1 2.00000000 secD2 0.00344828 secD12 0.00002000 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 10.00 usecP2 20.00 usec
PL1 2.00 dBPL1W 49.44866943 WSFO1 100.6130223 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1H
P3 14.80 usec
P4 29.60 usecPCPD2 90.00 usecPL2 1.50 dBPL12 17.18 dBPL2W 15.18650627 WPL12W 0.41063678 WSFO2 400.0926004 MHzSI 32768SF 100.6029626 MHzWDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
S52
ppm
1.52.02.53.03.54.04.55.05.56.0 ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
NAME madhu400 ope
EXPNO 214014
PROCNO 2093Date_ 20131217
Time 19.37INSTRUM spectPROBHD 5 mm PABBO BB-
PULPROG cosygpqf
TD 2048SOLVENT C6D6
NS 1DS 8SWH 2040.816 HzFIDRES 0.996492 Hz
AQ 0.5018100 secRG 80.6DW 245.000 usec
DE 6.50 usecTE 295.9 K
D0 0.00000300 sec
D1 1.48689198 secD13 0.00000400 secD16 0.00020000 sec
IN0 0.00049010 sec
======== CHANNEL f1 ========
NUC1 1H
P0 14.80 usecP1 14.80 usec
PL1 1.50 dB
PL1W 15.18650627 WSFO1 400.0923550 MHz
====== GRADIENT CHANNEL =====GPNAM1 SINE.100
GPZ1 10.00 %
P16 1000.00 usecND0 1TD 128
SFO1 400.0924 MHz
FIDRES 15.941180 HzSW 5.100 ppmFnMODE QF
SI 1024SF 400.0910000 MHzWDW SINE
SSB 0LB 0.00 HzGB 0PC 1.00
SI 1024
MC2 QFSF 400.0910000 MHz
WDW SINESSB 0LB 0.00 Hz
GB 0
S53
ppm
1.52.02.53.03.54.04.55.05.56.0 ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
NAME madhu400 ope
EXPNO 214015
PROCNO 2093Date_ 20131217Time 19.46INSTRUM spectPROBHD 5 mm PABBO BB-
PULPROG noesygpphTD 2048SOLVENT C6D6NS 32
DS 4SWH 2040.816 Hz
FIDRES 0.996492 Hz
AQ 0.5018100 secRG 181
DW 245.000 usecDE 6.50 usecTE 295.4 KD0 0.00022620 secD1 2.00000000 sec
D8 0.69999999 secD16 0.00020000 secIN0 0.00049010 sec
======== CHANNEL f1 ========
NUC1 1H
P1 14.80 usecP2 29.60 usecPL1 1.50 dB
PL1W 15.18650627 W
SFO1 400.0923550 MHz
====== GRADIENT CHANNEL =====GPNAM1 SINE.100
GPNAM2 SINE.100GPZ1 80.00 %GPZ2 40.00 %P16 1000.00 usecND0 1
TD 256
SFO1 400.0924 MHzFIDRES 7.970590 HzSW 5.100 ppm
FnMODE States-TPPISI 1024SF 400.0910000 MHzWDW QSINESSB 2LB 0.00 HzGB 0PC 1.00
SI 1024
MC2 States-TPPISF 400.0910000 MHzWDW QSINESSB 2LB 0.00 HzGB 0
S54
Data
Isolated neosemburin1
1H NMR, C6D6
Chemical shift, δ
Synthesized neosemburin
1H NMR, C6D6
Chemical shift, δ
1-H
3-H & 3'-H
5-H
6-H
6'-H
7-H
7'-H
9-H & 9'-H
10-H
11-H
5.47
4.10
2.49
1.61
1.23
3.52
4.16
1.50
5.08
1.30
5.42
4.07
2.47
1.60
1.21
3.48
4.12
1.47
5.05
1.28
Optical Rotation
[α] D 25: +8.3 (C 0.06, CHCl3)
[α]D25: +7.5 (C 0.06, CHCl3)
Table 1: Comparative spectral data of isolated and synthesised neosemburin (3)
[1] T. Sakai, Y. Nakagawa, T. Iwashita, Bull. Chem. Soc. Jpn. 1983, 56, 3477-3482.
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