benzylation cascade of 2-morpholinoanilines on water ... · supporting information...
TRANSCRIPT
S1
Supporting Information
Palladium-catalyzed dehydrative N-benzylation/C-H
benzylation cascade of 2-morpholinoanilines on water
Hidemasa Hikawa*, Risa Ichinose, Shoko Kikkawa and Isao Azumaya*
Faculty of Pharmaceutical Sciences, Toho University, Funabashi, Chiba 274-8510, Japan
[email protected] and [email protected]
1. Table of contents S12. Effects of catalysts and solvents S23. Competitive deuterium labeling experiment S34. Hammett study S45. Scale-up experiment S56. Copies of 1H and 13C NMR spectra of the all compounds S6-S36
Electronic Supplementary Material (ESI) for Green Chemistry.This journal is © The Royal Society of Chemistry 2018
S2
Effects of catalysts and solvents (see Table 1, entry 8).
A mixture of 2-morpholinoaniline 1a (178 mg, 1 mmol), palladium(II) acetate (11 mg, 0.05 mmol),
sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 36 mg, 0.1 mmol) and benzyl alcohol 2a (515
L, 5 mmol) in H2O (4 mL) was heated at 100 oC for 20 h in a sealed tube under Ar. After the reaction
mixture was cooled, 1,3,5-trimethoxybenzene (168.2 mg, 1 mmol, internal standard) was added to the
reaction mixture, which was extracted with CDCl3 (8 mL), then the organic layer was analyzed by 1H-
NMR spectroscopy.
abun
danc
e0
0.02
0.04
0.06
0.08
0.1
0.12
0.14
0.16
0.18
X : parts per Million : Proton
7.06.9 6.8 6.7 6.6 6.5 6.4 6.3 6.2 6.1 6.0 5.9 5.8 5.7 5.6 5.5 5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.5 4.4 4.3 4.2 4.1
6.
926
6.
922
6.
808
6.
805
6.
789
6.
615
6.
612
6.
596
6.
592
6.
286
6.
283
6.
264
6.
089
6.
049
5.
289
5.
099
4.
699
4.
558
4.
548
4.
535
4.
365
4.
209
3.00
0.95
0.95
91.4
2m
abun
danc
e0
0.1
0.2
X : parts per Million : Proton
7.06.9 6.8 6.7 6.6 6.5 6.4 6.3 6.2 6.1 6.0 5.9 5.8 5.7 5.6 5.5 5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.5 4.4 4.3 4.2 4.1
6.
947
6.
944
6.
928
6.
924
6.
810
6.
616
6.
613
6.
598
6.
595
6.
285
6.
282
6.
266
6.
262
5.
298
4.
552
11.4
2 5.01
3.93
1.00
1.00
1.00
0.99
0.98
0.96
Filename = M-HH7-81_Proton-1-7.jdfAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-81Solvent = CHLOROFORM-DCreation_Time = 5-OCT-2017 09:47:35Revision_Time = 21-NOV-2017 14:01:44Current_Time = 21-NOV-2017 14:23:55
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 21.7[dC]X_90_Width = 13.67[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
NH2
N
O
1a3a
Ph OH 2a (5 equiv)Pd catalyst (5 mol%)TPPMS (10 mol%)
100 oC, 20 h, Ar NH
N
O
PhPh
N
N
O
Ph
5not detected Ph
NH
PhPh
NO
3a
authentic sample
OMe
MeO OMe
S3
Competitive deuterium labeling experiment (see Scheme 4A).
H2O/D2O (1:1)100 oC, 16 h
2a (1 mmol)
NH
N
O
4a (0.25 mmol)
Ph OH
Pd(OAc)2 (5 mol%)TPPMS (10 mol%)
PhH
H
NH
N
O
D5-PhD
D4a-d (0.25 mmol)
D5-Ph OH
D D
2a-d (1 mmol)
NH
N
O
PhPh
H/D3a (kH/kD = 2.7)
A mixture of 4a (67.1 mg, 0.25 mmol), 4a-d (68.9 mg, 0.25 mmol), Pd(OAc)2 (6 mg, 0.025 mmol),
sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 18 mg, 0.05 mmol), benzyl alcohol 2a (108 mg,
1.0 mmol), and 2a-d (115 mg, 1.0 mmol) in H2O (1 mL) and D2O (1 mL) was heated at 100 oC for 16 h in
a sealed tube under air. After cooling, the reaction mixture was poured into water and extracted with
EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The
residue was washed with hexanes, then purified by flash column chromatography (silica gel,
hexanes/EtOAc) to give desired product 3a.
Signal 6.27 (Ar-H) 4.55 (methine-H)
Integral value 1.00 (1H) 0.73 (1H): kH/kD = 0.73/0.27 = 2.7
abun
danc
e0
0.1
0.2
X : parts per Million : Proton
6.3 6.2 6.1 6.0 5.9 5.8 5.7 5.6 5.5 5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.5 4.4
6.
285
6.
266
5.
289
5.
154
4.
564
4.
540
9.06
1.02
1.00
0.93
0.85
0.73
0.56
0.52
76.1
3m
57.5
6m
21.5
9m
16.1
5m
5.93
m
abun
danc
e0
0.1
0.2
X : parts per Million : Proton
6.3 6.2 6.1 6.0 5.9 5.8 5.7 5.6 5.5 5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.5 4.4
6.
285
6.
282
6.
266
6.
262
5.
298
4.
552
11.4
2
5.01
3.93
1.03
1.00
1.00
1.00
0.99
0.98
0.96
Filename = M-HH7-81_Proton-1-6.jdfAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-81Solvent = CHLOROFORM-DCreation_Time = 5-OCT-2017 09:47:35Revision_Time = 21-NOV-2017 12:59:10Current_Time = 21-NOV-2017 12:59:19
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 21.7[dC]X_90_Width = 13.67[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]NH
PhPh
NO
3a
authentic sample
S4
Hammett study (see Figure 4).
A mixture of 3- or 5-substituted 2-morpholinoanilines 1 (X = Me, Cl and CF3 groups) (0.25 mmol),
Pd(OAc)2 (6 mg, 0.025 mmol), sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 18 mg, 0.05
mmol) and benzylic alcohol 2a (258 L, 2.5 mmol) in H2O (2 mL) was heated at 120 oC in a sealed tube
under air. After cooling, the reaction mixture was poured into water and extracted with EtOAc. The
organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was
analyzed by 1H-NMR spectroscopy.
X = CF3: log(kX/kH) = log(1/9) = -0.95
abun
danc
e0
0.1
X : parts per Million : Proton
6.8 6.7 6.6 6.5 6.4 6.3 6.2 6.1 6.0
6.
826
6.
821
6.
816
6.
811
6.
803
6.
787
6.
784
6.
731
6.
711
6.
708
6.
693
6.
614
6.
611
6.
595
6.
591
6.
575
6.
572
6.
490
6.
290
6.
269
26.5
7 12.3
4
10.1
5
9.00
1.00
abun
danc
e0
0.1
0.2
0.3
X : parts per Million : Proton
6.9 6.8 6.7 6.6 6.5 6.4 6.3 6.2 6.1 6.0
6.
829
6.
826
6.
810
6.
807
6.
790
6.
787
6.
616
6.
613
6.
598
6.
595
6.
579
6.
575
6.
285
6.
282
6.
266
6.
262
11.4
2
5.01
3.93
1.00
1.00
1.00
0.99
0.98
0.96
abun
danc
e0
0.1
0.2
0.3
X : parts per Million : Proton
6.9 6.8 6.7 6.6 6.5 6.4 6.3 6.2 6.1 6.0
6.
855
6.
851
6.
835
6.
832
6.
485
6.
480
9.81
4.29
2.31
2.27
1.94
1.09
1.08
1.07
1.06
1.05
1.05
1.00
Filename = M-HH7-22-1-F1-CD_Proton-1-Author = deltaExperiment = proton.jxpSample_Id = M-HH7-22-1-F1-CDSolvent = CHLOROFORM-DCreation_Time = 15-SEP-2017 13:20:31Revision_Time = 21-NOV-2017 14:06:00Current_Time = 21-NOV-2017 14:06:06
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 22[dC]X_90_Width = 13.5[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.75[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
log(kX/kH)
5-Me (m) -0.07 0.17
H 0 0
3-Cl (m) 0.37 -0.6
5-Cl (m) 0.37 -1.02
5-CF3 (m) 0.43 -0.954
2a (2.5 mol)Ph OH
1X(0.25 mmol)
H2O, 120 oC
3X
Pd(OAc)2 (5 mol%)TPPMS (10 mol%)
NH2
NO
X
NH
NO
X
PhPh1a
(0.25 mmol)
NH2
NO
+
3a
NH
NO
PhPh
+
NH
PhPh
NO
3a
authentic sample
authentic sample
NH
PhPh
NO
3e
F3C
S5
Scale-up experiment (see Scheme 9).
2a(5 equiv)
NH2
N
O
100 oC, 16 h1a1.1 g
Ph OH
Pd(OAc)2 (5 mol%)TPPMS (10 mol%)
NH
N
O
PhPh
3a: 1.6 g (76%)
+
A mixture of 2-morpholinoaniline (1.07 g, 6 mmol), palladium(II) acetate (67.4 mg, 0.3 mmol),
TPPMS (218.6 mg, 0.6 mmol), and benzyl alcohol (2a, 3.09 mL, 30 mmol) in H2O (24 mL) was heated at
100 oC for 16 h under Ar. After cooling, the reaction mixture was poured into water and extracted with
EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The
residue was recrystallized from hexane/AcOEt to give desired product 3a (1.63 g, 4.55 mmol, 76%) as a
pale yellow solid.
After 10 min After 16 h
S6
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
351
7.
346
7.
328
7.
269
7.
256
7.
198
6.
928
6.
924
6.
598
6.
285
6.
282
6.
266
6.
262
5.
298
4.
552
3.
771
3.
227
3.
215
2.
993
2.
935
2.
638
0.
008
-0.
000
-0.
008
11.1
5
4.89
3.84
1.00
1.00
0.99
0.98
0.96
0.96
0.93
Filename = M-HH7-81_Proton-1-5.jdfAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-81Solvent = CHLOROFORM-DCreation_Time = 5-OCT-2017 09:47:35Revision_Time = 21-NOV-2017 12:56:10Current_Time = 21-NOV-2017 12:56:17
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 21.7[dC]X_90_Width = 13.67[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3a
NH
PhPh
NO
S7
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
143
.934
142
.389
138
.547
137
.927
129
.318
128
.621
128
.526
127
.001
126
.753
126
.228
125
.141
119
.564
116
.760
111
.564
77.
335
77.
011
76.
696
67.
772
59.
219
51.
735
45.
661
0.
000
Filename = M-HH7-81-C_Carbon-1-3.jdfAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-81-CSolvent = CHLOROFORM-DCreation_Time = 22-NOV-2017 14:03:40Revision_Time = 22-NOV-2017 14:17:14Current_Time = 22-NOV-2017 14:17:42
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 512Total_Scans = 512
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 21.9[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3a
NH
PhPh
NO
S8
abun
danc
e0
0.1
0.2
0.3
0.4
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
351
7.
346
7.
327
7.
276
7.
258
7.
186
6.
845
6.
825
6.
417
6.
414
6.
103
6.
099
5.
310
5.
300
4.
572
4.
561
4.
549
4.
538
4.
527
3.
785
3.
757
3.
215
3.
203
2.
986
2.
963
2.
852
2.
843
2.
079
0.
008
0.
000
-0.
008
13.4
1
5.08
4.01
3.20
1.11
1.07
1.04
1.02
1.01
1.00
Filename = M-HH7-70-4_Proton-1-7.jdfAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-70-4Solvent = CHLOROFORM-DCreation_Time = 21-OCT-2017 13:06:41Revision_Time = 21-NOV-2017 15:19:35Current_Time = 21-NOV-2017 15:19:49
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 52429Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 8.73463808[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 65536X_Prescans = 1X_Resolution = 0.11448671[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 21.6[dC]X_90_Width = 13.67[us]X_Acq_Time = 8.73463808[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 13.73463808[s]
3b
NH
PhPh
NO
Me
S9
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
144
.010
142
.294
137
.975
136
.211
134
.848
129
.318
128
.583
128
.478
126
.934
126
.705
126
.228
119
.554
117
.170
112
.260
77.
335
77.
221
77.
011
76.
696
67.
819
59.
076
51.
983
45.
623
21.
424
0.
000
Filename = M-HH7-70-4-C_Carbon-1-5.jdAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-70-4-CSolvent = CHLOROFORM-DCreation_Time = 22-OCT-2017 09:20:15Revision_Time = 21-NOV-2017 15:23:55Current_Time = 21-NOV-2017 15:24:06
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 12000Total_Scans = 12000
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22.2[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3b
NH
PhPh
NO
Me
S10
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
311
7.
303
7.
288
7.
268
7.
258
7.
256
6.
755
6.
735
6.
496
6.
166
6.
002
5.
991
4.
636
4.
623
4.
612
4.
600
4.
589
3.
919
3.
896
3.
701
3.
685
3.
325
3.
318
3.
025
3.
002
2.
590
2.
562
2.
254
2.
226
-0.
000
-0.
008
11.6
3
3.02
2.02
1.03
1.03
1.02
1.01
1.01
1.01
1.00
1.00
1.00
0.97
Filename = M-HH7-70-2_Proton-1-6.jdfAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-70-2Solvent = CHLOROFORM-DCreation_Time = 11-SEP-2017 12:37:55Revision_Time = 21-NOV-2017 15:47:58Current_Time = 21-NOV-2017 15:48:17
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 22[dC]X_90_Width = 13.5[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.75[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3c
NH
PhPh
NOCl
S11
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
146
.823
143
.391
137
.632
133
.541
132
.206
129
.203
128
.669
128
.583
127
.592
127
.144
126
.858
126
.171
117
.971
109
.705
77.
335
77.
020
76.
696
68.
382
68.
086
58.
514
48.
703
48.
674
45.
203
-0.
000
Filename = M-HH7-70-2-C_Carbon-1-3.jdAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-70-2-CSolvent = CHLOROFORM-DCreation_Time = 30-SEP-2017 18:46:40Revision_Time = 2-OCT-2017 13:08:16Current_Time = 21-NOV-2017 15:49:46
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = TRUEScans = 1024Total_Scans = 1024
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22.3[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3c
NH
PhPh
NOCl
S12
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
X : parts per Million : Proton
7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
331
7.
327
7.
289
7.
270
7.
257
7.
174
6.
810
6.
550
6.
544
6.
233
6.
227
5.
360
5.
349
4.
556
4.
544
4.
533
4.
521
4.
510
3.
747
3.
230
3.
219
2.
983
2.
960
2.
593
-0.
000
9.79
3.99
3.54
2.06
1.06
1.04
1.01
1.00
1.00
0.99
0.97
Filename = M-HH7-70-3-F2-2_Proton-1-9Author = deltaExperiment = proton.jxpSample_Id = M-HH7-70-3-F2-2Solvent = CHLOROFORM-DCreation_Time = 11-OCT-2017 09:14:24Revision_Time = 21-NOV-2017 15:54:50Current_Time = 21-NOV-2017 15:55:09
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 22.1[dC]X_90_Width = 13.67[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3d
NH
PhPh
NO
Cl
S13
abun
danc
e0
0.1
0.2
0.3
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
143
.486
143
.057
137
.632
137
.060
130
.719
129
.260
128
.765
128
.583
127
.277
126
.858
126
.142
120
.708
116
.312
111
.326
77.
335
77.
221
77.
020
76.
696
67.
667
58.
933
51.
811
45.
442
0.
000
Filename = M-HH7-70-3-F2-C_Carbon-1-4Author = deltaExperiment = carbon.jxpSample_Id = M-HH7-70-3-F2-CSolvent = CHLOROFORM-DCreation_Time = 14-OCT-2017 14:54:59Revision_Time = 16-OCT-2017 09:49:08Current_Time = 21-NOV-2017 15:56:34
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 35000Total_Scans = 35000
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 21.9[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3d
NH
PhPh
NO
Cl
S14
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
1.9
2.0
2.1
2.2
2.3
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
345
7.
339
7.
331
7.
300
7.
282
7.
257
6.
963
6.
944
6.
485
6.
480
5.
302
5.
292
4.
600
4.
589
4.
577
4.
566
4.
553
3.
772
3.
253
3.
241
3.
015
2.
992
2.
662
-0.
000
9.23
4.03
2.18
2.14
1.83
1.03
1.01
1.01
1.00
1.00
0.99
0.99
Filename = M-HH7-22-1-F1-CD_Proton-1-Author = deltaExperiment = proton.jxpSample_Id = M-HH7-22-1-F1-CDSolvent = CHLOROFORM-DCreation_Time = 15-SEP-2017 13:20:31Revision_Time = 21-NOV-2017 16:00:49Current_Time = 21-NOV-2017 16:01:05
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 22[dC]X_90_Width = 13.5[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.75[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3e
NH
PhPh
NO
F3C
S15
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
150
.953
143
.878
129
.824
129
.033
128
.852
127
.574
127
.069
126
.764
113
.539
107
.094
107
.056
107
.017
67.
096
58.
792
51.
250
44.
661
40.
533
40.
323
40.
113
39.
904
39.
694
39.
484
39.
274
Filename = M-HH7-22-1-F1_Carbon-1-3.jAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-22-1-F1Solvent = DMSO-D6Creation_Time = 26-SEP-2017 23:33:13Revision_Time = 21-NOV-2017 16:03:01Current_Time = 21-NOV-2017 16:03:26
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 8000Total_Scans = 8000
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22.4[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3e
NH
PhPh
NO
F3C
S16
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
1.3
1.4
1.5
1.6
1.7
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
299
7.
277
7.
191
7.
170
6.
852
6.
850
6.
466
6.
204
6.
200
6.
183
5.
212
5.
198
4.
475
4.
463
4.
451
4.
440
4.
427
3.
708
3.
689
3.
338
3.
263
3.
011
2.
904
2.
879
2.
567
2.
537
9.97
5.12
2.03
2.01
1.98
1.71
1.04
1.02
1.02
1.00
0.99
0.98
0.96
Filename = M-HH7-21-1-F2_Proton-1-4.jAuthor = deltaExperiment = proton.jxpSample_Id = M-HH6-21-1-F2Solvent = DMSO-D6Creation_Time = 11-NOV-2016 13:59:50Revision_Time = 21-NOV-2017 16:08:01Current_Time = 21-NOV-2017 16:08:20
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 34Temp_Get = 20.2[dC]X_90_Width = 13.1[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.55[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3f
NH
NO
MeO
OMe
S17
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
158
.542
158
.409
142
.286
138
.825
136
.537
130
.816
130
.787
127
.822
125
.066
119
.756
116
.714
114
.264
114
.187
111
.413
67.
363
58.
420
55.
521
55.
483
51.
841
44.
328
40.
571
40.
361
40.
151
39.
942
39.
732
39.
532
39.
322
Filename = M-HH7-21-1-F2-C_Carbon-1-4Author = deltaExperiment = carbon.jxpSample_Id = M-HH7-21-1-F2-CSolvent = DMSO-D6Creation_Time = 2-OCT-2017 02:44:43Revision_Time = 2-OCT-2017 12:59:03Current_Time = 21-NOV-2017 16:09:19
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 4000Total_Scans = 4000
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22.2[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3f
NH
NO
MeO
OMe
S18
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
226
7.
204
7.
064
7.
042
6.
852
6.
831
6.
811
6.
789
6.
591
6.
306
6.
304
6.
283
5.
252
5.
243
4.
454
4.
443
4.
432
4.
420
4.
000
3.
982
3.
784
3.
110
3.
097
2.
915
2.
668
1.
423
1.
411
1.
406
1.
394
1.
387
1.
376
-0.
000
6.45
5.28
4.18
3.61
3.09
2.14
1.93
1.84
1.06
1.05
1.04
1.03
1.02
1.00
Filename = M-HH7-21-5_Proton-1-6.jdfAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-21-5Solvent = CHLOROFORM-DCreation_Time = 30-SEP-2017 11:24:41Revision_Time = 21-NOV-2017 16:12:55Current_Time = 21-NOV-2017 16:13:07
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 34Temp_Get = 22[dC]X_90_Width = 13.67[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3g
NH
NO
EtO
OEt
S19
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
157
.874
157
.750
142
.504
138
.518
135
.811
130
.300
129
.842
127
.258
125
.132
119
.468
116
.627
114
.463
114
.434
111
.631
77.
335
77.
020
76.
706
67.
781
63.
434
63.
367
58.
733
51.
744
44.
870
14.
903
14.
845
-0.
000
Filename = M-HH7-21-5-C_Carbon-1-3.jdAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-21-5-CSolvent = CHLOROFORM-DCreation_Time = 1-OCT-2017 09:32:34Revision_Time = 2-OCT-2017 13:02:49Current_Time = 21-NOV-2017 16:13:57
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 3551Total_Scans = 3551
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22.1[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3g
NH
NO
EtO
OEt
S20
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
257
7.
228
7.
206
6.
813
6.
792
6.
591
6.
306
6.
302
6.
285
6.
283
5.
246
5.
237
4.
448
4.
436
4.
426
4.
416
3.
938
3.
918
3.
780
3.
719
3.
110
3.
099
2.
906
2.
663
1.
761
1.
743
1.
738
1.
724
1.
548
1.
485
0.
990
0.
981
0.
971
0.
962
-0.
000
6.54
5.23
5.15
4.92
4.25
4.12
3.24
1.90
1.70
1.07
1.06
1.03
1.01
1.00
0.93
Filename = M-HH7-89-5-nBu-di_Proton-1Author = deltaExperiment = proton.jxpSample_Id = M-HH7-nBu-diSolvent = CHLOROFORM-DCreation_Time = 5-OCT-2017 09:30:32Revision_Time = 21-NOV-2017 16:16:22Current_Time = 21-NOV-2017 16:16:38
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 34Temp_Get = 21.6[dC]X_90_Width = 13.67[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3h
NH
NO
nBuO
OnBu
S21
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
158
.083
157
.969
142
.532
138
.518
135
.763
130
.261
129
.785
127
.220
125
.122
119
.459
116
.608
114
.472
111
.640
77.
335
77.
221
77.
020
76.
706
67.
781
67.
715
58.
762
51.
735
44.
908
31.
407
31.
312
19.
288
19.
231
13.
892
13.
854
-0.
000
Filename = M-HH7-89-5-C_Carbon-1-3.jdAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-89-5-CSolvent = CHLOROFORM-DCreation_Time = 24-NOV-2017 09:19:18Revision_Time = 24-NOV-2017 10:51:25Current_Time = 24-NOV-2017 10:52:00
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 1220Total_Scans = 1220
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 21.8[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3h
NH
NO
nBuO
OnBu
S22
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
290
7.
270
7.
185
7.
164
7.
128
7.
104
6.
872
6.
868
6.
474
6.
194
6.
173
5.
231
5.
219
4.
513
4.
501
4.
489
4.
478
4.
465
3.
713
3.
335
3.
312
3.
053
2.
930
2.
907
2.
502
2.
267
1.
990
1.
174
-0.
000
6.50
6.42
4.40
4.07
2.20
2.16
2.12
1.39
1.13
1.10
1.10
1.09
1.09
1.08
1.03
1.00
Filename = M-HH7-21-3-F1_Proton-1-8.jAuthor = deltaExperiment = proton.jxpSample_Id = M-HH6-21-3-F1Solvent = DMSO-D6Creation_Time = 11-NOV-2016 14:05:39Revision_Time = 22-NOV-2017 10:30:51Current_Time = 22-NOV-2017 10:31:00
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 20.2[dC]X_90_Width = 13.1[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.55[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3i
NH
NO
Me
Me
S23
abun
danc
e-0
.01
00.
010.
020.
030.
040.
050.
060.
070.
080.
090.
10.
110.
120.
130.
140.
150.
16
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
142
.267
141
.704
138
.815
136
.241
135
.955
135
.821
129
.710
129
.500
129
.367
126
.687
125
.066
119
.765
116
.724
111
.375
67.
335
40.
609
40.
399
40.
199
39.
989
39.
780
39.
570
39.
360
21.
197
21.
168
Filename = M-HH7-21-3-F1_Carbon-1-4.jAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-21-3-F1Solvent = DMSO-D6Creation_Time = 1-OCT-2017 00:57:50Revision_Time = 22-NOV-2017 10:32:32Current_Time = 22-NOV-2017 10:32:43
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 6000Total_Scans = 6000
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22.1[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3i
NH
NO
Me
Me
S24
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
1.9
2.0
2.1
2.2
2.3
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
317
7.
297
7.
257
7.
199
7.
179
7.
152
6.
922
6.
904
6.
579
6.
294
6.
277
6.
275
5.
252
5.
243
4.
513
4.
503
4.
488
4.
478
4.
467
3.
751
3.
198
3.
187
2.
902
2.
866
2.
589
1.
260
1.
257
1.
243
1.
239
1.
222
1.
205
-0.
000
12.4
3
6.34
5.02
4.05
2.17
1.34
1.04
1.03
1.03
1.01
1.01
1.00
0.96
Filename = M-HH7-28-2-iso_Proton-1-8.Author = deltaExperiment = proton.jxpSample_Id = M-HH7-28-2-isoSolvent = CHLOROFORM-DCreation_Time = 22-SEP-2017 09:30:51Revision_Time = 22-NOV-2017 10:36:04Current_Time = 22-NOV-2017 10:36:14
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 21.9[dC]X_90_Width = 13.67[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3j
NH
NO
iPr
iPr
S25
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
147
.433
147
.328
142
.685
141
.589
138
.509
135
.525
129
.174
126
.657
126
.591
126
.019
125
.132
119
.487
116
.532
111
.545
77.
335
77.
020
76.
696
67.
781
58.
981
51.
687
45.
461
33.
743
33.
714
24.
065
24.
008
-0.
000
Filename = M-HH7-28-2-C_Carbon-1-4.jdAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-28-2-CSolvent = CHLOROFORM-DCreation_Time = 30-SEP-2017 16:55:08Revision_Time = 2-OCT-2017 13:04:46Current_Time = 22-NOV-2017 10:38:14
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 2048Total_Scans = 2048
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22.3[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3j
NH
NO
iPr
iPr
S26
abun
danc
e0
1.0
2.0
3.0
4.0
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
259
7.
234
7.
214
7.
174
7.
154
7.
109
6.
837
6.
818
6.
552
6.
327
6.
324
6.
306
5.
382
5.
038
5.
026
5.
016
3.
913
3.
810
3.
160
3.
149
3.
080
3.
058
2.
729
-0.
000
10.0
4
7.07
4.06
3.84
2.09
1.03
1.01
1.00
1.00
1.00
0.90
Filename = M-HH7-28-4-F3-re_Proton-1-Author = deltaExperiment = proton.jxpSample_Id = M-HH7-28-4-F3-reSolvent = CHLOROFORM-DCreation_Time = 29-NOV-2017 11:43:15Revision_Time = 29-NOV-2017 12:28:20Current_Time = 29-NOV-2017 12:28:42
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 46Temp_Get = 21.5[dC]X_90_Width = 11.69[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 1.5[dB]X_Pulse = 5.845[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3k
NH
NO
OMeOMe
S27
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
X : parts per Million : Carbon13
220.0210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
157
.931
156
.872
131
.987
130
.843
127
.620
127
.554
126
.858
125
.065
120
.660
120
.345
119
.220
116
.026
111
.154
110
.563
110
.401
77.
335
77.
221
77.
020
76.
696
67.
791
55.
634
55.
434
52.
602
51.
696
36.
708
0.
000
Filename = M-HH7-28-4-F3-C_Carbon-1-4Author = deltaExperiment = carbon.jxpSample_Id = M-HH7-28-4-F3-CSolvent = CHLOROFORM-DCreation_Time = 29-NOV-2017 14:10:13Revision_Time = 29-NOV-2017 15:48:11Current_Time = 29-NOV-2017 15:48:44
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 1024Total_Scans = 1024
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22[dC]X_90_Width = 9.36[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.12[us]Irr_Atn_Dec = 20.394[dB]Irr_Atn_Noe = 20.394[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3k
NH
NO
OMeOMe
S28
abun
danc
e0
0.2
0.4
0.6
0.8
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
3.0
3.2
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
332
7.
322
7.
276
7.
259
7.
179
7.
162
6.
941
6.
920
6.
466
5.
386
5.
375
4.
567
4.
554
4.
544
4.
533
4.
521
3.
244
3.
231
3.
209
3.
196
3.
039
3.
017
3.
005
2.
983
2.
855
2.
640
1.
668
-0.
000
11.5
8
6.50
4.46
1.01
1.00
0.99
0.98
0.97
0.93
Filename = M-HH7-47-1-F1-CDCl3_ProtonAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-47-1-F1-CDCl3Solvent = CHLOROFORM-DCreation_Time = 21-JAN-2017 13:23:29Revision_Time = 22-NOV-2017 11:22:46Current_Time = 22-NOV-2017 11:22:59
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 44Temp_Get = 20.6[dC]X_90_Width = 11.55[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 1.5[dB]X_Pulse = 5.775[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
3l
NH
PhPh
N
F3C
S29
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
X : parts per Million : Carbon13
220.0210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
143
.152
142
.256
137
.727
129
.346
128
.679
128
.478
127
.220
126
.228
107
.340
107
.302
107
.264
107
.226
77.
631
77.
335
77.
221
77.
011
76.
696
59.
353
52.
555
45.
413
26.
830
24.
275
0.
000
Filename = M-HH7-47-1-F1_Carbon-1-5.jAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-47-1-F1Solvent = CHLOROFORM-DCreation_Time = 26-SEP-2017 16:40:19Revision_Time = 22-NOV-2017 11:24:51Current_Time = 22-NOV-2017 11:25:22
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 8000Total_Scans = 8000
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22.4[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
3l
NH
PhPh
N
F3C
S30
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
1.3
1.4
1.5
1.6
1.7
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
356
7.
348
7.
344
7.
269
7.
257
7.
026
6.
714
6.
711
6.
614
6.
611
6.
595
6.
591
5.
159
4.
375
4.
361
3.
829
2.
944
2.
932
2.
921
1.
561
0.
008
0.
000
-0.
008
4.08
3.92
3.92
2.07
2.04
1.84
1.01
1.00
0.95
Filename = M-HH7-30_Proton-1-5.jdfAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-30Solvent = CHLOROFORM-DCreation_Time = 22-NOV-2016 13:20:51Revision_Time = 1-DEC-2017 12:58:12Current_Time = 1-DEC-2017 12:58:18
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 21.6[dC]X_90_Width = 13.1[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.55[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
4aNH
NO
Ph
S31
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
1.3
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
143
.154
139
.931
138
.606
128
.718
127
.145
127
.107
125
.438
119
.641
117
.134
110
.622
77.
441
77.
127
76.
802
67.
821
51.
889
48.
189
Filename = M-HH7-30-C_Carbon-1-2.jdfAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-30-CSolvent = CHLOROFORM-DCreation_Time = 24-NOV-2017 10:28:32Revision_Time = 24-NOV-2017 10:49:51Current_Time = 24-NOV-2017 10:50:13
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 352Total_Scans = 352
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 21.9[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
4aNH
NO
Ph
S32
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
1.3
1.4
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
307
7.
254
7.
047
7.
032
7.
025
7.
004
6.
996
6.
722
6.
718
6.
574
6.
571
6.
554
6.
551
5.
144
4.
330
3.
828
2.
936
2.
924
2.
913
-0.
000
4.23
4.23
4.09
2.07
2.01
1.00
1.00
0.95
Filename = M-HH7-28-1_Proton-1-5.jdfAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-28-1Solvent = CHLOROFORM-DCreation_Time = 27-SEP-2017 06:26:53Revision_Time = 22-NOV-2017 11:33:52Current_Time = 22-NOV-2017 11:34:12
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 34Temp_Get = 22[dC]X_90_Width = 13.67[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
4b
NH
NO
F
S33
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
1.9
2.0
2.1
2.2
2.3
2.4
2.5
2.6
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
163
.137
160
.705
142
.857
138
.547
135
.477
135
.439
128
.555
128
.478
125
.332
119
.621
117
.228
115
.521
115
.311
110
.525
77.
354
77.
240
77.
039
76.
725
67.
696
51.
792
47.
444
-0.
000
Filename = M-HH7-28-1-C_Carbon-1-7.jdAuthor = deltaExperiment = carbon.jxpSample_Id = M-HH7-28-1-CSolvent = CHLOROFORM-DCreation_Time = 1-OCT-2017 12:41:38Revision_Time = 22-NOV-2017 11:36:04Current_Time = 22-NOV-2017 11:36:19
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 4000Total_Scans = 4000
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 22.2[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
4b
NH
NO
F
S34
abun
danc
e0
0.1
0.2
0.3
0.4
0.5
0.6
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
258
7.
252
7.
046
7.
026
7.
021
7.
017
6.
997
6.
978
6.
729
6.
710
6.
705
6.
692
6.
613
6.
593
5.
138
3.
828
2.
944
2.
938
2.
932
2.
921
-0.
000
4.38
4.32
2.12
1.10
1.04
1.00
0.95
Filename = M-HH7-33-D_Proton-1-4.jdfAuthor = deltaExperiment = proton.jxpSample_Id = M-HH7-33-DSolvent = CHLOROFORM-DCreation_Time = 22-NOV-2016 13:29:40Revision_Time = 22-NOV-2017 11:43:34Current_Time = 22-NOV-2017 11:44:33
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 36Temp_Get = 21.6[dC]X_90_Width = 13.1[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.55[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
4b-d
NO
NHDD
D
D
DD
D
S35
abun
danc
e0
0.2
0.4
0.6
0.8
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
3.0
3.2
X : parts per Million : Proton
8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
7.
266
7.
261
7.
251
7.
248
7.
238
7.
235
7.
221
7.
095
7.
091
7.
075
7.
001
6.
999
6.
990
6.
986
4.
352
3.
875
3.
864
3.
852
3.
281
3.
270
3.
259
0.
000
6.96
4.53
4.34
4.22
4.02
1.91
1.00
0.97
Filename = ric-013-Ndi_Proton-1-6.jdfAuthor = deltaExperiment = proton.jxpSample_Id = ric-013-NdiSolvent = CHLOROFORM-DCreation_Time = 18-NOV-2017 09:49:39Revision_Time = 22-NOV-2017 11:39:06Current_Time = 22-NOV-2017 11:39:17
Comment = single_pulseData_Format = 1D COMPLEXDim_Size = 13107Dim_Title = ProtonDim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 2.18365952[s]X_Domain = 1HX_Freq = 399.78219838[MHz]X_Offset = 5[ppm]X_Points = 16384X_Prescans = 1X_Resolution = 0.45794685[Hz]X_Sweep = 7.5030012[kHz]X_Sweep_Clipped = 6.00240096[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Tri_Domain = ProtonTri_Freq = 399.78219838[MHz]Tri_Offset = 5[ppm]Clipped = FALSEScans = 8Total_Scans = 8
Relaxation_Delay = 5[s]Recvr_Gain = 34Temp_Get = 21.6[dC]X_90_Width = 13.67[us]X_Acq_Time = 2.18365952[s]X_Angle = 45[deg]X_Atn = 2.2[dB]X_Pulse = 6.835[us]Irr_Mode = OffTri_Mode = OffDante_Presat = FALSEInitial_Wait = 1[s]Repetition_Time = 7.18365952[s]
N
NO
Ph
Ph5
S36
abun
danc
e0
1.0
2.0
3.0
4.0
X : parts per Million : Carbon13
220.0 210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0
144
.364
143
.668
138
.367
129
.004
128
.270
126
.992
123
.112
122
.702
121
.891
118
.821
77.
489
77.
174
76.
860
67.
659
53.
576
50.
592
Filename = M-ric-013-C_Carbon-1-4.jdfAuthor = deltaExperiment = carbon.jxpSample_Id = M-ric-013-CSolvent = CHLOROFORM-DCreation_Time = 22-NOV-2017 10:23:28Revision_Time = 22-NOV-2017 12:24:00Current_Time = 22-NOV-2017 12:24:17
Comment = single pulse decoupled gatData_Format = 1D COMPLEXDim_Size = 26214Dim_Title = Carbon13Dim_Units = [ppm]Dimensions = XSite = JNM-ECS400Spectrometer = DELTA2_NMR
Field_Strength = 9.389766[T] (400[MHz])X_Acq_Duration = 1.04333312[s]X_Domain = 13CX_Freq = 100.52530333[MHz]X_Offset = 100[ppm]X_Points = 32768X_Prescans = 4X_Resolution = 0.95846665[Hz]X_Sweep = 31.40703518[kHz]X_Sweep_Clipped = 25.12562814[kHz]Irr_Domain = ProtonIrr_Freq = 399.78219838[MHz]Irr_Offset = 5[ppm]Clipped = FALSEScans = 160Total_Scans = 160
Relaxation_Delay = 2[s]Recvr_Gain = 60Temp_Get = 21.8[dC]X_90_Width = 9.74[us]X_Acq_Time = 1.04333312[s]X_Angle = 30[deg]X_Atn = 3.3[dB]X_Pulse = 3.24666667[us]Irr_Atn_Dec = 20.699[dB]Irr_Atn_Noe = 20.699[dB]Irr_Noise = WALTZIrr_Pwidth = 0.115[ms]Decoupling = TRUEInitial_Wait = 1[s]Noe = TRUENoe_Time = 2[s]Repetition_Time = 3.04333312[s]
N
NO
Ph
Ph5