JOC SI 0326(proof)
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- ゆたか よしなが
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1 1 Supporting Information Stereochemistry of N-Benzoyl-5-substituted-1-benzazepines Revisited: Synthesis of the Conformationally Biased Derivatives and Revision of the Reported Structure Hidetsugu Tabata, Tetsuya Yoneda, Tomohiko Tasaka, Shigekazu Ito, Tetsuta Oshitari, Hideyo Takahashi, and Hideaki Natsugari* Contents 1. Comparison of anti/syn isomers in the 1 H NMR spectra of IIa-c and IIIa-c H NMR analytical data of Ib (major) VT-NMR spectra at elevated temperatures and determination of G value between the anti and syn forms for Ia, IIa, and IIIa VT-NMR spectra of Ib and Ic at lower temperatures Energy differences between the conformers determined by DFT calculation Atomic coordinates for the lowest-energy conformers by DFT calculation Thermal ellipsoid plots (ORTEP drawing) of compounds Ib, Ic, IIc and IIIa H NMR spectra of Ia and IIa measured in CD 3OD H-, 13 C-, and 2D-NMR (NOESY, COSY, and HMQC) spectra Reference. 70
2 2 1. Comparison of anti/syn isomers in the 1 H NMR spectra of IIa-c and IIIa-c. Compounds IIa c: Figure S1. 1 H NMR spectra (600 MHz in DMSO-d 6): (a) IIa, (b) IIb (before separation of the anti/syn isomers), and (c) IIc. The descriptors a and e are used for the stereochemical arrangement of the proton, axial and equatorial orientation, respectively. The assignment of the signals from the anti and syn isomers are shown in blue and red, respectively.
3 3 Compounds IIIa c: Figure S2. 1 H NMR spectra (600 MHz in DMSO-d 6): (a) IIIa, (b) IIIb (before separation of the anti/syn isomers), and (c) IIIc. The descriptors a and e are used for the stereochemical arrangement of the proton, axial and equatorial orientation, respectively. The assignment of the signals from the anti and syn isomers are shown in blue and red, respectively.unidentified peaks (presumably originating in the trans isomer) in IIIb and IIIc are marked by x.
4 H NMR analytical data of Ib (major): Chemical shifts and coupling (Table S1), relation of the coupling of the ring protons (Table S2), and relation between 3 J values and torsion angles (Table S3). Table S3. Torsion angles and observed vicinal coupling ( 3 J) torsion angles (º) 3 torsion angles (º) J (Hz) by the X-ray analysis a by the Karplus equation b H 2eq -C2-C3-H 3eq H 2eq -C2-C3-H 3ax H 2ax -C2-C3-H 3ax H 2ax -C2-C3-H 3eq H 3ax -C3-C4-H 4eq H 3ax -C3-C4-H 4ax H 3eq -C3-C4-H 4eq H 3eq -C3-C4-H 4ax H 4eq -C4-C5-H 5ax H 4ax -C4-C5-H 5ax (H 2eq, H 3eq ) (H 2eq, H 3ax ) (H 2ax, H 3ax ) (H 2ax, H 3eq ) (H 3ax, H 4eq ) (H 3ax, H 4ax ) (H 3eq, H 4eq ) (H 3eq, H 4ax ) (H 4eq, H 5ax ) (H 4ax, H 5ax ) 180 a Obtained from the CIF of Ib (Molecule I). b Estimated angles from the observed 3 J values.
5 5 3. VT-NMR spectra at elevated temperatures and determination of G value between the anti and syn forms for Ia, IIa, and IIIa. G = 69.5 kj/mol Tc = 383 K (in DMSO-d 6) Figure S3. VT-NMR of Ia. G = 68.8 kj/mol Tc = 333 K (in DMSO-d 6) Figure S4. VT-NMR of IIa.
6 6 N(CH 3 ) 2 N O llia 393 K 373 K G = 71.0 kj/mol Tc = 353 K (in DMSO-d 6) 353 K 333 K 313 K 296 K Figure S5. VT-NMR of IIIa. 3. VT-NMR spectra of Ib and Ic at lower temperatures Figure S6. VT NMR of Ib.
7 Figure S7. VT-NMR of Ic: Although the signals in the syn isomer of Ic apparently did not show any change, broadening was observed at around 253 K. See Ref. 15 in the main text. 4. Energy differences between the conformers determined by HF/DFT calculation (Tables S4 S9). Conformer generations were performed for Ia, Ib, Ic, IIa, IIc, and IIIa. Tables S1 S6 show the energy differences of the conformers in comparison with the lowest-energy conformer determined by HF/DFT calculation, s1 i.e., E values determined using UFF, RHF/6-31G(d,p), RB3LYP/6-31G(d,p), and B3LYP/6-311+G(d,p) levels, and G values determined using the B3LYP/6-311+G(d,p) level. The right column of the tables shows the geometry type of the conformers determined using the B3LYP/6-311+G(d,p) level, and the following abbreviations are used: E (E), Z (Z), anti (A), syn (S), chair (C), and boat (B), and when the azepine ring adopts the twisted form, (T) is added. For example, the E-anti-boat conformer is expressed as E-A-B, and if the ring adopts the twisted boat form, E-A-B(T) is used.
8 8 Table S4-1. Compound Ia Ia ID No. UFF RHF/STO-3G RHF/6-31G(d,p) E /kcal/mol E /hartree RB3LYP/6-31G(d,p) G /hartree RB3LYP/6-311+G(d,p) RB3LYP/6-311+G(d,p)
9 9 Table S4-2. Compound Ia Ia ID No. UFF RHF/6-31G(d,p) RB3LYP/6-31G(d,p) ΔE (kj/mol) ΔE (kj/mol) ΔG (kj/mol) E-A- C(T) Z-A- B Z-S- B(T) E-A- B ) ) ) ) E-A- C 6) E-S- B(T) Z-A- C E-S- B(T) ) E-S- C E-A- B Z-S- C E-S- B(T) ) E : kcal/mol, 2) E : hartree (h), 3) E : h, 4) E : h, 5) G : h, 6) The lowest-energy conformer. RB3LYP/6-311+G(d,p) Geometry type of conformers
10 10 Table S5-1. Compound Ib Ib ID No. UFF RHF/STO-3G RHF/6-31G(d,p) E / kcal/mol E / hartree RB3LYP/6-31G(d,p) RB3LYP/6-311+G(d,p) RB3LYP/6-311+G(d,p) G / hartree
11 11 Table S6-2. Compound Ib RHF/6- Ib UFF 31G(d,p) ID No. ΔE (kj/mol) RB3LYP/ 6-31G(d,p) ΔE (kj/mol)δg (kj/mol) ) E-S- C Z-S -C Z-S- B(T) Z-A -C ) ) ) ) E-A- C 6) Z-S- B(T) E-A- C(T) Z-A- B E-S- B(T) E-A- B E-A- C Z-S- B(T) E-S- B(T) Z-A-B 1) E : kcal/mol, 2) E : hartree (h), 3) E : h, 4) E : h 5) G : h, 6) The lowest-energy conformer. RB3LYP/6-311+G(d,p) Geometry type of conformers
12 12 Table S6-1. Compound Ic Ic ID No. UFF RHF/STO-3G RHF/6-31G(d,p) E / kcal/mol E / hartree RB3LYP/6-31G(d,p) RB3LYP/6-311+G(d,p) RB3LYP/6-311+G(d,p) G / hartree
13 13 Table S6-2. Compound Ic RHF/6- Ic UFF 31G(d,p) ID No. ΔE (kj/mol) RB3LYP/ 6-31G(d,p) ΔE (kj/mol) ΔG (kj/mol) Z-S- B(T) E-S- B(T) Z-S- C E-A- C ) ) ) ) ) E-S- C 6) E-A- C(T) E-A- B E-S- B(T) E-S- B(T) E-S- B(T) E-S- B(T) ) E : kcal/mol, 2) E : hartree (h), 3) E : h, 4) E : h, 5) G : h, 6) The lowest-energy conformer. RB3LYP/6-311+G(d,p) Geometry type of conformers
14 14 Table S7-1. Compound IIa IIa ID No. UFF RHF/STO-3G RHF/6-31G(d,p) E / kcal/mol E / hartree RB3LYP/6-31G(d,p) RB3LYP/6-311+G(d,p) RB3LYP/6-311+G(d,p) G / hartree
15 15 Table S7-2. Compound IIa IIa ID No. UFF RHF/6-31G(d,p) ΔE (kj/mol) RB3LYP/ 6-31G(d,p) ΔE (kj/mol) ΔG (kj/mol) ) ) ) ) E-A- C 6) ) E-S- C E-A- B Z-S- C Z-A- C E-A-C ) E : kcal/mol, 2) E : hartree (h), 3) E : h, 4) E : h, 5) G : h, 6) The lowest-energy conformer. RB3LYP/6-311+G(d,p) Geometry type of conformers
16 16 Table S8-1. Compound IIc IIc ID No. UFF RHF/STO-3G RHF/6-31G(d,p) E / kcal/mol E / hartree RB3LYP/6-31G(d,p) RB3LYP/6-311+G(d,p) RB3LYP/6-311+G(d,p) G / hartree
17 17 Table S8-2. Compound IIc IIc ID No. UFF RHF/6-31G(d,p) ΔE (kj/mol) RB3LYP/6-31G(d,p) ΔE (kj/mol) ΔG (kj/mol) ) ) ) ) E-S- C 6) E-S- C E-S- B(T) E-A- B E-A- C E-S- B E-S- B(T) E-A- C(T) E-A- C(T) Z-S- B(T) ) ) E : kcal/mol, 2) E : hartree (h), 3) E : h, 4) E : h, 5) G : h, 6) The lowest-energy conformer. RB3LYP/6-31G(d,p) Geometry type of conformers
18 18 Table S9-1. Compound IIIa RHF/6- RB3LYP/6- RB3LYP/6- RB3LYP/6- IIIa UFF RHF/STO-3G 31G(d,p) 31G(d,p) 311+G(d,p) 311+G(d,p) ID No. E / kcal/mol E / hartree G / hartree
19 Table S9-2. Compound IIIa IIIa ID No. UFF RHF/6-31G(d,p) ΔE (kj/mol) RB3LYP/ 6-31G(d,p) ΔE (kj/mol) ΔG (kj/mol) E-S -C(T) E-S- C ) ) 0.38 E-A- B ) Z-S- C ) ) E-A- C 6) E-A- C E-S- C E-A- C E-A- C E-S- C E-S- C 1) E : kcal/mol, 2) E : hartree (h), 3) E : h, 4) E : h, 5) G : h, 6) The lowest-energy conformer. RB3LYP/6-311+G(d,p) Geometry type of conformers 19
20 5. Atomic coordinates for the lowest-energy conformers by DFT calculation (Tables S10 S16). Atomic coordinates obtained by the calculation using the RB3LYP/6-311+G(d,p) level are shown for the lowest-energy conformers. As for the compound IIIa, those of the 2 nd lowest-energy conformer is also shown. Table S10. Ia: ID No. 6 (the lowest energy conformaer) Gibbs Free Energy (298.15K, 1 atm) hartree Total Energy Atom x hartree y z C C C C C C C C N C C C C O C C C C C C H H H H H H H H H H H H H H H H H H H
21 21 Table S11. Ib: ID No.5 (the lowest energy conformer) Gibbs Free Energy (298.15K, 1 atm) hartree Total Energy Atom x hartree y z C C C C C C C C C C C C C C C C C C O N Cl H H H H H H H H H H H H H H H H H H
22 22 Table S12. Ic: ID No.6 (the lowest-energy conformer) Gibbs Free Energy (298.15K, 1 atm) hartree Total Energy Atom x hartree y z C C C C C C C C C C C C C C C C C C C O N H H H H H H H H H H H H H H H H H H H H H
23 23 Table S13. IIa: ID No.2 (the lowest-energy conformer) Gibbs Free Energy (298.15K, 1 atm) hartree Total Energy Atom x hartree y z C C C C C C C C C C C C C C C C C O N C O H H H H H H H H H H H H H H H H H H H
24 24 Table S14. IIc: ID No.2 (the lowest-energy conformer) Gibbs Free Energy (298.15K, 1 atm) hartree Total Energy Atom x hartree y z C C C C C C C C C C C C C C C C C C O N C O H H H H H H H H H H H H H H H H H H H H H
25 25 Table S15. IIIa (1): ID No. 27 (the lowest-energy conformer) Gibbs Free Energy (298.15K, 1 atm) hartree Total Energy Atom x hartree y z C C C C C C C C O N C C C C N C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H
26 26 Table S16. IIIa (2): ID No.19 (the 2nd lowest-energy conformer) Gibbs Free Energy (298.15K, 1 atm) hartree Total Energy Atom x hartree y z C C C C C C C C O N C C C C N C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H
27 27 6. Thermal ellipsoid plots (ORTEP drawing) of compounds Ib, Ic, IIc and IIIa. (the ellipsoid contour: 50 % probability levels) Ib Molecule I (chair) Ib Molecule II (boat) Ic IIc IIIa
28 H NMR spectra of Ia and IIa measured in CD 3OD at 296K. 1 H NMR (CD 3OD) of Ia = single_pulse Creation_Time = 11-MAY :54: Current_Time = 30-JAN :30: anti : syn Data_Format = 1D COMPLEX Dim_Size = Dim_Title = Proton 1 : 0.24 Dim_Units = [] Dimensions = X = 42ZTY _rt_Pr Machine = CWBFFBBXFX Revision_Time = 30-JAN :30: Sample_Id = 42ZTY Spectrometer = DELTA2_NMR Probe_Recovery = 5[us] Scans = 16 Mod_Return = 1 Total_Scans = 16 X_Points = X_Prescans = 1 = 5[] = [kHz] _ = [kHz] X_Resolution = [Hz] Irr_Domain = Proton Irr_Offset = 5[] Tri_Domain = Proton Tri_Offset = 5[] X_Acq_Duration = [s] Digital_Filter = TRUE Filter_Factor = 8 Af_Version = 1 X90 = 7.88[us] Delay_Of_Start = [s] Actual_Start_Time = 11-MAY :54: Acq_Delay = 10.88[us] Digital_Filter_Status = 2P Dc_Balanced Af_Delay_Ratio = 0 Autoshim_Mode = AUTOSHIM OFF Buffer_Loop = 1 Buffer_Loop_Index = 1 Changer_Slot = 0 Changer_Slot_Position = 0 Collection_State = Collect End_Time = 11-MAY :55: Experiment = proton.jxp Exp_Remaining = 1[s] Ia sexp( 0.2[Hz], 0.0[s] ) 1 H NMR (CD 3OD) of IIa IIa anti : syn 11 : : m sexp( 0.2[Hz], 0.0[s] ) zerofill( 16 ) 以以に由由 :: 42JHTA _Proton-1-1.jdf = 42JHTA _Proton-1-6 Experiment = proton.jxp Sample_Id = 42JHTA = METHANOL-D4 Creation_Time = 11-MAY :12:03 Revision_Time = 30-JAN :16:49 Current_Time = 30-JAN :40:30 = single_pulse Dim_Size = Dim_Title = Proton Dim_Units = [] X_Acq_Duration = [s] = 5[] X_Points = X_Prescans = 1 X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Tri_Offset = 5[] Scans = 8 Total_Scans = 8 Relaxation_Delay = 5[s] Recvr_Gain = 42 = 22.7[dC] X_90_Width = 7.88[us] X_Acq_Time = [s] = 45[deg] = 3.94[us] Irr_Mode Tri_Mode Dante_Presat Repetition_Time = [s]
29 H-, 13 C-, and 2D-NMR spectra for new compounds: 2D-NMR (NOESY, COSY, and HMQC) spectra are shown for Ib d, IIa c, and IIIa c. 1 H NMR (CDCl 3) (5c) c sexp( 0.2[Hz], 0.0[s] ) 以以に由由 :: 42JHTA _Proton-1-1.jdf = 42JHTA _Proton-1-4. Experiment = proton.jxp Sample_Id = 42JHTA Creation_Time = 9-AUG :25:47 Revision_Time = 5-JAN :43:27 Current_Time = 5-JAN :43:31 = single_pulse Dim_Size = Dim_Title = Proton Dim_Units = [] X_Acq_Duration = [s] = 5[] X_Points = X_Prescans = 1 X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Tri_Offset = 5[] Scans = 32 Total_Scans = 32 Relaxation_Delay = 5[s] Recvr_Gain = 40 = 22.7[dC] X_90_Width = 8[us] X_Acq_Time = [s] = 45[deg] = 4[us] Irr_Mode Tri_Mode Dante_Presat Repetition_Time = [s] 13 C NMR (CDCl 3) (5c) Relaxation_Delay = 2[s] Recvr_Gain = 58 = 23[dC] X_90_Width = 10.6[us] X_Acq_Time = [s] = 30[deg] = 12[dB] = [us] Irr_Atn_Dec = [dB] Irr_Atn_Noe = [dB] Irr_Noise = WALTZ Irr_Pwidth = 76[us] Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = [s] X : parts per Million : Carbon13 5c sexp( 2.0[Hz], 0.0[s] ) 以以に由由 :: 42JHTA _Carbon-1-1.jdf = 42JHTA _Carbon-1-3. Experiment = carbon.jxp Sample_Id = 42JHTA Creation_Time = 9-AUG :31:29 Revision_Time = 5-JAN :08:50 Current_Time = 5-JAN :08:56 = single pulse decoupled gat Dim_Size = Dim_Title = Carbon13 Dim_Units = [] X_Acq_Duration = [s] = 13C = [MHz] = 100[] X_Points = X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Scans = 1700 Total_Scans = 1700
30 30 1 H NMR (CDCl 3) (6c) c sexp( 0.2[Hz], 0.0[s] ) 以以に由由 :: 42JHTA _Proton-1-1.jdf = 42JHTA _Proton-1- Experiment = proton.jxp Sample_Id = 42JHTA Creation_Time = 12-AUG :10:11 Revision_Time = 5-JAN :51:15 Current_Time = 5-JAN :51:18 = single_pulse Dim_Size = Dim_Title = Proton Dim_Units = [] X_Acq_Duration = [s] = 5[] X_Points = X_Prescans = 1 X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Tri_Offset = 5[] Scans = 64 Total_Scans = 64 Relaxation_Delay = 5[s] Recvr_Gain = 44 = 22.5[dC] X_90_Width = 8[us] X_Acq_Time = [s] = 45[deg] = 4[us] Irr_Mode Tri_Mode Dante_Presat Repetition_Time = [s] 13 C NMR (CDCl 3) (6c) Relaxation_Delay = 2[s] Recvr_Gain = 58 = 22.6[dC] X_90_Width = 10.6[us] X_Acq_Time = [s] = 30[deg] = 12[dB] = [us] Irr_Atn_Dec = [dB] Irr_Atn_Noe = [dB] Irr_Noise = WALTZ Irr_Pwidth = 76[us] Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = [s] X : parts per Million : Carbon c sexp( 2.0[Hz], 0.0[s] ) 以以に由由 :: 42JHTA _Carbon-1-1.jdf = 42JHTA _Carbon-1- Experiment = carbon.jxp Sample_Id = 42JHTA Creation_Time = 12-AUG :19:38 Revision_Time = 5-JAN :07:43 Current_Time = 5-JAN :07:56 = single pulse decoupled gat Dim_Size = Dim_Title = Carbon13 Dim_Units = [] X_Acq_Duration = [s] = 13C = [MHz] = 100[] X_Points = X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Scans = 1700 Total_Scans = 1700
31 31 1 H NMR (CDCl 3) (8) sexp( 0.2[Hz], 0.0[s] ) 以以に由由 :: 42ZTY _Proton-1-1.jdf = 42ZTY _Proton-1-3.jd Experiment = proton.jxp Sample_Id = 42ZTY Creation_Time = 28-OCT :07:34 Revision_Time = 10-DEC :31:50 Current_Time = 10-DEC :32:05 = single_pulse Dim_Size = Dim_Title = Proton Dim_Units = [] X_Acq_Duration = [s] = 5[] X_Points = X_Prescans = 1 X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Tri_Offset = 5[] Scans = 16 Total_Scans = 16 Relaxation_Delay = 5[s] Recvr_Gain = 40 = 22.8[dC] X_90_Width = 8[us] X_Acq_Time = [s] = 45[deg] = 4[us] Irr_Mode Tri_Mode Dante_Presat Repetition_Time = [s] 13 C NMR (CDCl 3) (8) sexp( 2.0[Hz], 0.0[s] ) 以以に由由 :: 42ZTY _Carbon-1-1.jdf = 42ZTY _Carbon-1-3.jd Experiment = carbon.jxp Sample_Id = 42ZTY Creation_Time = 28-OCT :11:36 Revision_Time = 10-DEC :32:25 Current_Time = 10-DEC :32:52 = single pulse decoupled gat Dim_Size = Dim_Title = Carbon13 Dim_Units = [] X_Acq_Duration = [s] = 13C = [MHz] = 100[] X_Points = X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Scans = 4000 Total_Scans = 4000 Relaxation_Delay = 2[s] Recvr_Gain = 58 = 23[dC] X_90_Width = 10.6[us] X_Acq_Time = [s] = 30[deg] = 12[dB] = [us] Irr_Atn_Dec = [dB] Irr_Atn_Noe = [dB] Irr_Noise = WALTZ Irr_Pwidth = 76[us] Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = [s] X : parts per Million : Carbon13
32 32 1 H NMR (CDCl 3) (Ib) Cl CH 3 N O Ib 65.57m m 98.83m 79.86m sexp( 0.2[Hz], 0.0[s] ) 以以に由由 :: 42ZTY4-3-36_Proton-1-1.jdf = 42ZTY4-3-36_Proton-1-7.jdf Experiment = proton.jxp Sample_Id = 42ZTY Creation_Time = 18-JUL :03:02 Revision_Time = 5-JAN :20:00 Current_Time = 5-JAN :20:04 = single_pulse Dim_Size = Dim_Title = Proton Dim_Units = [] X_Acq_Duration = [s] = 5[] X_Points = X_Prescans = 1 X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Tri_Offset = 5[] Scans = 8 Total_Scans = 8 Relaxation_Delay = 5[s] Recvr_Gain = 42 = 22.3[dC] X_90_Width = 8.5[us] X_Acq_Time = [s] = 45[deg] = 4.25[us] Irr_Mode Tri_Mode Dante_Presat Repetition_Time = [s] 13 C NMR (CDCl 3) (Ib) Relaxation_Delay = 2[s] Recvr_Gain = 58 = 23.6[dC] X_90_Width = 10.6[us] X_Acq_Time = [s] = 30[deg] = 12[dB] = [us] Irr_Atn_Dec = [dB] Irr_Atn_Noe = [dB] Irr_Noise = WALTZ Irr_Pwidth = 76[us] Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = [s] X : parts per Million : Carbon13 Cl CH 3 N O Ib sexp( 2.0[Hz], 0.0[s] ) 以以に由由 :: 42ZTY4-3-26_Carbon-1-1.jdf = 42ZTY4-3-26_Carbon-1-3.jdf Experiment = carbon.jxp Sample_Id = 42ZTY Creation_Time = 10-DEC :59:08 Revision_Time = 5-JAN :37:02 Current_Time = 5-JAN :37:07 = single pulse decoupled gat Dim_Size = Dim_Title = Carbon13 Dim_Units = [] X_Acq_Duration = [s] = 13C = [MHz] = 100[] X_Points = X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Scans = 4000 Total_Scans = 4000
33 33 NOESY NMR (CDCl 3) (Ib) Y : parts per Million : Proton sexp( 5.0[Hz], 0.0[s] ) sexp( 5.0[Hz], 0.0[s] ) zerofill( 2 ) = 42ZTY4-3-36_NOESY-1-3.jdf Experiment = noesy.jxp Sample_Id = 42ZTY Creation_Time = 18-JUL :11:15 Revision_Time = 10-DEC :12:42 Current_Time = 10-DEC :14:14 = phase sensitive noesy Data_Format = 2D COMPLEX COMPLEX Dim_Size = 819, 512 Dim_Title = Proton Proton Dim_Units = [] [] Y X_Acq_Duration = [s] = 4.5[] X_Points = 1024 X_Resolution = [Hz] = [kHz] _ = [kHz] Y_Domain Y_Freq Y_Offset = 4.5[] Y_Points = 256 Y_Prescans = 0 Y_Resolution = [Hz] Y_Sweep = [kHz] Irr_Offset = 5[] Tri_Offset = 5[] Scans = 4 Total_Scans = 1024 Relaxation_Delay = 1.5[s] Recvr_Gain = 46 = 22.5[dC] Mix_Time = 1[s] X_Acq_Time = [s] = 8.5[us] Y_Acq_Time = [ms] Y_P1_Correction = 180 Ib COSY NMR (CDCl 3) (Ib) dc_balance sexp : 0.2[Hz] trapezoid : 0[%] : 0[%] : 80[%] : 100[%] zerofill : 1 fft : 1 Y : parts per Million : Proton = gradient absolute Creation_Time = 18-JUL :05: Current_Time = 5-FEB :12: Data_Format = 2D REAL REAL Dim_Size = 1024, 1024 Dim_Title = Proton Proton Dim_Units = [] [] Dimensions = X Y = 42ZTY4-3-36_COSY_f Machine = CWBFFBBXFX Revision_Time = 18-JUL :33: Sample_Id = 42ZTY Spectrometer = DELTA2_NMR Probe_Recovery = 5[us] Scans = 4 Mod_Return = 1 Total_Scans = 1024 X_Points = 1280 = 5[] = [kHz] _ = [kHz] X_Resolution = [Hz] Y_Points = 256 Y_Prescans = 0 Y_Domain Y_Offset = 5[] Y_Freq Y_Sweep = [kHz] Y_Resolution = [Hz] Irr_Domain = Proton Irr_Offset = 5[] Tri_Domain = Proton Tri_Offset = 5[] X_Acq_Duration = [s] Digital_Filter = TRUE Filter_Factor = 4 Af_Version = 1 X90 = 8.5[us] Delay_Of_Start = [s] Actual_Start_Time = 18-JUL :06: Acq_Delay = 21.74[us] Digital_Filter_Status = NP Dc_Balanced Af_Delay_Ratio = 0 Autoshim_Mode = AUTOSHIM OFF Buffer_Loop = 1
34 34 Ib HMQC NMR (CDCl 3) (Ib) Y : parts per Million : Carbon sinbell4 : -60 : 160 zerofill : 1 fft : 1 sinbell4 : -60 : 160 zerofill : 2 fft : 1 abs = gradient enhanced Creation_Time = 1-AUG :03: Current_Time = 5-FEB :20: Data_Format = 2D REAL REAL Dim_Size = 819, 512 Dim_Title = Proton Carbon13 Dim_Units = [] [] Dimensions = X Y = 42ZTY4-3-36_HMQC_f Machine = CWBFFBBXFX Revision_Time = 1-AUG :58: Sample_Id = 42ZTY Spectrometer = DELTA2_NMR Probe_Recovery = 5[us] Scans = 8 Mod_Return = 1 Total_Scans = 2048 X_Points = 1024 = 5[] = [kHz] _ = [kHz] X_Resolution = [Hz] Y_Points = 256 Y_Prescans = 0 Y_Domain = 13C Y_Offset = [] Y_Freq = [MHz] Y_Sweep = [kHz] Y_Resolution = [Hz] Tri_Domain = Proton Tri_Offset = 5[] X_Acq_Duration = [ms] Digital_Filter = TRUE Filter_Factor = 4 Af_Version = 1 X90 = 8.5[us] Delay_Of_Start = [s] Actual_Start_Time = 1-AUG :03: Acq_Delay = 21.74[us] Digital_Filter_Status = 2P Dc_Balanced Af_Delay_Ratio = 0 Autoshim_Mode = AUTOSHIM OFF Buffer_Loop = 1 Buffer_Loop_Index = 1 Changer_Slot = 0 Changer_Slot_Position = 0
35 35 1 H NMR (CDCl 3) (Ic) Ic sexp( 0.2[Hz], 0.0[s] ) 以以に由由 :: HTA CDCl3_Proton-1-1.jdf = HTA CDCl3_Proton-1- Experiment = proton.jxp Sample_Id = 42JHTA Creation_Time = 29-OCT :35:53 Revision_Time = 5-JAN :15:20 Current_Time = 5-JAN :15:28 = single_pulse Dim_Size = Dim_Title = Proton Dim_Units = [] X_Acq_Duration = [s] = 5[] X_Points = X_Prescans = 1 X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Tri_Offset = 5[] Scans = 64 Total_Scans = 64 Relaxation_Delay = 5[s] Recvr_Gain = 42 = 23.5[dC] X_90_Width = 8[us] X_Acq_Time = [s] = 45[deg] = 4[us] Irr_Mode Tri_Mode Dante_Presat Repetition_Time = [s] 13 C NMR (CDCl 3) (Ic) Relaxation_Delay = 2[s] Recvr_Gain = 58 = 21.7[dC] X_90_Width = 10.6[us] X_Acq_Time = [s] = 30[deg] = 12[dB] = [us] Irr_Atn_Dec = [dB] Irr_Atn_Noe = [dB] Irr_Noise = WALTZ Irr_Pwidth = 76[us] Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = [s] X : parts per Million : Carbon13 Ic sexp( 2.0[Hz], 0.0[s] ) 以以に由由 :: HTA CDCl3_Carbon-1-1.jdf = HTA CDCl3_Carbon-1- Experiment = carbon.jxp Sample_Id = 42JHTA Creation_Time = 29-OCT :45:10 Revision_Time = 5-JAN :11:07 Current_Time = 5-JAN :11:21 = single pulse decoupled gat Dim_Size = Dim_Title = Carbon13 Dim_Units = [] X_Acq_Duration = [s] = 13C = [MHz] = 100[] X_Points = X_Resolution = [Hz] = [kHz] _ = [kHz] Irr_Offset = 5[] Scans = 4000 Total_Scans = 4000
36 36 NOESY NMR (CD 2Cl 2) (Ic) Y : parts per Million : Proton sexp( 5.0[Hz], 0.0[s] ) sexp( 5.0[Hz], 0.0[s] ) zerofill( 2 ) = HTA _NOESY-1-3.jdf Experiment = noesy.jxp Sample_Id = 42JHTA = METHYLENE-CHLORIDE-D2 Creation_Time = 18-JAN :11:31 Revision_Time = 10-DEC :04:23 Current_Time = 10-DEC :05:48 = phase sensitive noesy Data_Format = 2D COMPLEX COMPLEX Dim_Size = 819, 512 Dim_Title = Proton Proton Dim_Units = [] [] Y X_Acq_Duration = [s] = 4[] X_Points = 1024 X_Resolution = [Hz] = [kHz] _ = [kHz] Y_Domain Y_Freq Y_Offset = 4[] Y_Points = 256 Y_Prescans = 0 Y_Resolution = [Hz] Y_Sweep = [kHz] Irr_Offset = 5[] Tri_Offset = 5[] Scans = 8 Total_Scans = 2048 Relaxation_Delay = 1.5[s] Recvr_Gain = 46 = 24[dC] Mix_Time = [s] X_Acq_Time = [s] = 8.5[us] Y_Acq_Time = [ms] Y_P1_Correction = Ic COSY NMR (CD 2Cl 2) (Ic) Y : parts per Million : Proton sinbell_auto sinbell_auto zerofill( 4 ) abs symmetrize( Cosy, 24 ) = HTA _COSY-1-3.jdf Experiment = cosy.jxp Sample_Id = 42JHTA = METHYLENE-CHLORIDE-D2 Creation_Time = 18-JAN :37:02 Revision_Time = 30-JAN :13:19 Current_Time = 30-JAN :14:59 = gradient absolute value co Data_Format = 2D REAL REAL Dim_Size = 1024, 1024 Dim_Title = Proton Proton Dim_Units = [] [] Y X_Acq_Duration = [s] = 4[] X_Points = 1280 X_Resolution = [Hz] = [kHz] _ = [kHz] Y_Domain Y_Freq Y_Offset = 4[] Y_Points = 256 Y_Prescans = 0 Y_Resolution = [Hz] Y_Sweep = [kHz] Irr_Offset = 5[] Tri_Offset = 5[] Scans = 21 Total_Scans = 5376 Relaxation_Delay = 1.5[s] Recvr_Gain = 48 = 22.7[dC] X_90_Width = 8.5[us] X_Acq_Time = [s] = 8.5[us] Y_Acq_Time = [ms] Irr_Mode
37 37 Ic HMQC NMR (CD 2Cl 2) (Ic) Y : parts per Million : Carbon sinbell4( -60, 160 ) sinbell4( -60, 160 ) zerofill( 2 ) abs = HTA _HMQC-1-3.jd Experiment = hmqc.jxp Sample_Id = 42JHTA = METHYLENE-CHLORIDE-D2 Creation_Time = 18-JAN :15:54 Revision_Time = 30-JAN :23:11 Current_Time = 30-JAN :24:22 = gradient enhanced HMQC Data_Format = 2D REAL REAL Dim_Size = 819, 512 Dim_Title = Proton Carbon13 Dim_Units = [] [] Dimensions = X Y Field_Strength = [T] (600[MHz X_Acq_Duration = [s] = 4[] X_Points = 1024 X_Resolution = [Hz] = [kHz] _ = [kHz] Y_Domain = 13C Y_Freq = [MHz] Y_Offset = 95[] Y_Points = 256 Y_Prescans = 0 Y_Resolution = [Hz] Y_Sweep = [kHz] Tri_Domain = Proton Tri_Offset = 5[] Scans = 21 Total_Scans = 5376 Relaxation_Delay = 1.5[s] Recvr_Gain = 90 = 23.2[dC] X_Acq_Time = [s] X_Gamma = = 8.5[us] Y_Acq_Time = [ms] Y_Atn = 12[dB] Y_Gamma = Y_Pulse = 11.2[us] Irr_Atn_Dec = 31.8[dB]
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