Chem 203 December 20, Final Exam Part II Problem 1 of 3 (30 points)

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Name: Chem 203 December 20, 2014 Final Exam Part II Problem 1 of 3 (30 points) Select and submit TWO OUT OF THE THREE PROBLEMS FROM PART II for grading. Do not submit three problems. If you wish to unstaple the pages, please initial each page. Books, notes, lecture videos, calculators, rulers, and laptop computers are permitted as is wireless (or wired) internet access and appropriate software (e.g, Pymol, Macromodel/Maestro, Excel, NMRPrediction, Chemdraw, ElComp, MolE, etc.). Catalogs of molecular structures (e.g., the Aldrich catalog, the Merck Index, etc.) or databases of molecular structures (such as wireless access to SciFinder Scholar, the Sigma-Aldrich website, etc.) are NOT PERMITTED. USE OF SUCH ITEMS CONSTITUTES ACADEMIC DISHNONESTY, WILL RESULT IN A FAILING GRADE (F) IN THE CLASS, AND MAY RESULT IN EXPULSION FROM THE Ph.D. PROGRAM. 1 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution International License.

The following spectral data are provided for a compound with a molecular formula C 10 H 17 NO 2 : IR (thin film from CHCl 3 on salt plates), 500 MHz 1 H NMR, 125.8 MHz 13 C NMR, DEPT-90, DEPT-135, COSY, HMQC, HMBC, TOCSY (100 ms mixing time), NOESY and a 1D NOE experiment. All NMR spectra were measured in CDCl 3 solution. Using these data, determine the structure of the compound and assign all of the 1 H and 13 C resonances to their respective atoms in the structure. Make sure to determine the stereochemistry of the compound and to clearly assign 1 H resonances to the appropriate diastereotopic protons. MAKE SURE TO COMPLETELY ANSWER THE QUESTIONS a-f ON PAGES 2-4. a. Write the structure of the molecule. If there are any aspects of your structure that don't seem to make sense, please feel free to comment on them below: b. Build an energy-minimized molecular model of the molecule using PyMOL and the "clean" function. Use the side menu (S) to show each molecule as sticks (Show-sticks). Use the pulldown menu to display each molecule in maximum quality with (Display-Quality-Maximum Quality). Save the.pse files as Problem_II.1.pse. E-mail the.pse files to me (jsnowick@uci.edu). Alternatively, you may build an energy-minimized model of the correct diastereomer using Maestro/MacroModel with the MMFF force field. E-mail me (jsnowick@uci.edu) the -out.maegz file associated with that model. 2 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution International License.

c. Tabulate the shifts of the 1 H resonances (a-j) in order of descending chemical shift. Provide an appropriate name for each multiplet (e.g., s, d, t, q, quintet, sextet, septet, octet, dd, ddd, dt, td, dddd, tt, qd, dq, etc.) and list its coupling constants in appropriate order; also list its integral [e.g., a: 3.30 (t, J = 7.3 Hz, 3 H)]. If a resonance is not described by a well-defined multiplet, name it as m and give its range [e.g., c: 4.43-4.37 (m, 2 H)]. a: b: c: d: e: f: g: h: i: j: d. Redraw the structure of the molecule below and write the letter (a-j) of each 1 H resonance next to the proton or protons to which it corresponds. If the assignment of a particular resonance is uncertain, please indicate this. 3 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution International License.

e. Tabulate the shifts of the 13 C resonances (1-10) in order of descending chemical shift. Make sure to report the chemical shift of each carbon resonances to the nearest tenth of, unless two have the same value, in which case you may report it to the nearest hundredth. 1: 2: 3: 4: 5: 6: 7: 8: 9: 10: f. Redraw the structure of the molecule below and write the number (1-10) of each 13 C resonance next to the carbon or carbons to which it corresponds. If the assignment of particular resonance is uncertain, please indicate this. 4 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution International License.

Varian Resolutions Pro 120 110 100 90 % Transmittance 80 70 60 50 40 X H 2 O 30 20 10 0 1711.8 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 Wavenumber

1H spectrum Integral 000 113 082 215 0.9981 092 0.9475 2.9812 6.0010 7.25984 4.15928 4.14366 4.12689 3.85796 3.84537 3.84152 3.82819 3.61053 3.59704 3.58951 3.58277 3.57652 3.56269 2.76896 2.74943 2.73447 2.73032 2.71521 2.69561 2.48795 2.47652 2.46243 2.45382 2.44217 2.42848 2.16811 2.15534 2.14868 2.13688 1.67958 1.66630 1.65834 1.65302 1.64556 1.63252 1.46559 2962 1612 0.88441 0.87103 h i j EXPNO 1 Date_ 20141204 Time 22.32 PULPROG zg30 TD 128202 NS 64 DS 2 SWH 8012.820 Hz FIDRES 0.062502 Hz AQ 7.9998546 sec RG 3.2 DW 62.400 usec D1 0.10000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec SFO1 500.2235015 MHz SI 65536 WDW EM LB 0.30 Hz PC 0 a b c d e f g 1D NMR plot parameters CX 22.80 cm CY 15.00 cm F1P 9.000 F1 4501.98 Hz F2P -0.500 F2-250.11 Hz PPMCM 0.41667 /cm HZCM 208.42502 Hz/cm CHCl 3 8 7 6 5 4 3 2 1 0

DU=/v, USER=nmr14t, NAME= Act II A, EXPNO=1, PROCNO=1 F1=9.000, F2=0.000, MI=0.50cm, MAXI=10000.00cm, PC=00 # ADDRESS FREQUENCY INTENSITY [Hz] [PPM] 1 31431.7 36316 7.2598 1.35 2 44116.8 2080.552 4.1593 1.66 3 44180.7 2072.742 4.1437 3.02 4 44249.3 2064.353 4.1269 1.91 5 45349.6 1929.829 3.8580 1.81 6 45401.1 1923.530 3.8454 2.40 7 45416.8 1921.605 3.8415 1.82 8 45471.4 1914.936 3.8282 1.74 9 46361.9 1806.061 3.6105 0.92 10 46417.1 1799.312 3.5970 1.61 11 46447.9 1795.543 3.5895 1.23 12 46475.5 1792.173 3.5828 1.17 13 4650 1789.046 3.5765 5 14 46557.6 1782.129 3.5627 0.80 15 49805.0 1385.088 2.7690 0.73 16 49884.9 1375.317 2.7494 1 17 49946.1 1367.837 2.7345 1.22 18 49963.0 1365.761 2.7303 0.98 19 50024.8 1358.204 2.7152 1.92 20 50105.0 1348.397 2.6956 4 21 50954.6 1244.523 2.4880 0.97 22 51001.4 1238.807 2.4765 1.39 23 51059.0 1231.757 2.4624 1.15 24 51094.3 1227.448 2.4538 0.80 25 51141.9 1221.620 2.4422 1.15 26 51197.9 1214.776 2.4285 0.84 27 52263.2 1084.531 2.1681 3.48 28 52315.4 1078.143 2.1553 3.17 29 52342.7 1074.812 2.1487 3.54 30 5239 1068.907 2.1369 2.24 31 54261.9 840.159 1.6796 0.83 32 54316.2 833.517 1.6663 1.20 33 54348.8 829.532 1.6583 6 34 54370.5 826.874 1.6530 7 35 54401.1 823.141 1.6456 1.15 36 54454.4 816.619 1.6325 0.82 37 55137.4 733.117 1.4656 15.00 38 5692 515.037 296 8.84 39 56976.3 508.281 161 8.76 40 57515.1 442.401 0.8844 8.84 41 57569.9 435.705 0.8710 8.88

1H spectrum Integral 000 113 082 4.15928 4.14366 4.12689 3.85796 3.84537 3.84152 3.82819 3.61053 3.59704 3.58951 3.58277 3.57652 3.56269 a b c EXPNO 1 Date_ 20141204 Time 22.32 PULPROG zg30 TD 128202 NS 64 DS 2 SWH 8012.820 Hz FIDRES 0.062502 Hz AQ 7.9998546 sec RG 3.2 DW 62.400 usec D1 0.10000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec SFO1 500.2235015 MHz SI 65536 WDW EM LB 0.30 Hz PC 0 1D NMR plot parameters CX 22.80 cm CY 15.00 cm F1P 4.500 F1 2250.99 Hz F2P 3.000 F2 1500.66 Hz PPMCM 0.06579 /cm HZCM 32.90921 Hz/cm 4.4 4.2 3.8 3.6 3.4 3.2

1H spectrum Integral 215 0.9981 092 0.9475 0.0292 2.76896 2.74943 2.73447 2.73032 2.71521 2.69561 2.48795 2.47652 2.46243 2.45382 2.44217 2.42848 2.16811 2.15534 2.14868 2.13688 2.10782 1.69280 1.67958 1.66630 1.65834 1.65302 1.64556 1.63252 1.61939 9101 f EXPNO 1 d e g Date_ 20141204 Time 22.32 PULPROG zg30 TD 128202 NS 64 DS 2 SWH 8012.820 Hz FIDRES 0.062502 Hz AQ 7.9998546 sec RG 3.2 DW 62.400 usec D1 0.10000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec SFO1 500.2235015 MHz SI 65536 WDW EM LB 0.30 Hz PC 0 1D NMR plot parameters CX 22.80 cm CY 15.00 cm F1P 3.000 F1 1500.66 Hz F2P 00 F2 750.33 Hz PPMCM 0.06579 /cm HZCM 32.90921 Hz/cm 2.8 2.6 2.4 2.2 1.8 1.6

1H spectrum Integral 2.9521 6.0010 1.46559 2962 1612 0.88441 0.87103 h EXPNO 1 i j Date_ 20141204 Time 22.32 PULPROG zg30 TD 128202 NS 64 DS 2 SWH 8012.820 Hz FIDRES 0.062502 Hz AQ 7.9998546 sec RG 3.2 DW 62.400 usec D1 0.10000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec SFO1 500.2235015 MHz SI 65536 WDW EM LB 0.30 Hz PC 0 1D NMR plot parameters CX 22.80 cm CY 15.00 cm F1P 00 F1 750.33 Hz F2P -0.000 F2-0.00 Hz PPMCM 0.06579 /cm HZCM 32.90921 Hz/cm 1.4 1.2 0.8 0.6 0.4 0.2

Z-restored spin-echo 13C spectrum with 1H decoupling 179.05 13C{1H} dept135 100.02 1 2 3 4 5 6 7 8 9 10 77.41 77.16 76.91 CDCl 3 CHCl 3 77 61.76 39 33.58 33.12 25.08 20.64 19.14 EXPNO 2 Date_ 20141204 Time 23.35 PULPROG SpinEchopg30gp.prd TD 65536 NS 1024 DS 16 SWH 30303.031 Hz FIDRES 0.462388 Hz AQ 813940 sec RG 7298.2 DW 16.500 usec D1 0.25000000 sec d11 0.03000000 sec d17 0.00019600 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec P2 33.10 usec NUC1 13C P1 16.55 usec P11 500.00 usec P12 2000.00 usec PL0 120.00 db PL1-0 db SFO1 125.7942548 MHz SP1 2.70 db SP2 2.70 db SPNAM1 Crp60,0.5,20.1 SPNAM2 Crp60comp.4 SPOFF1 0.00 Hz SPOFF2 0.00 Hz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 100.00 usec PL2 1.60 db PL12 24.50 db SFO2 500.2225011 MHz GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ1 30.00 % GPZ2 50.00 % p15 500.00 usec p16 1000.00 usec SI 65536 SF 125.7804117 MHz WDW EM LB 0 Hz PC 0 1D NMR plot parameters CX 22.80 cm CY 3.56 cm F1P 185.000 F1 23269.38 Hz F2P 15.000 F2 1886.70 Hz PPMCM 7.45614 /cm HZCM 937.83643 Hz/cm dept90 CHCl 3 160 140 120 100 80 60 40 20

Z-restored spin-echo 13C spectrum with 1H decoupling 13C{1H} dept135 387 33.582 33.115 5 6 7 8 9 10 25.085 20.641 19.140 EXPNO 2 Date_ 20141204 Time 23.35 PULPROG SpinEchopg30gp.prd TD 65536 NS 1024 DS 16 SWH 30303.031 Hz FIDRES 0.462388 Hz AQ 813940 sec RG 7298.2 DW 16.500 usec D1 0.25000000 sec d11 0.03000000 sec d17 0.00019600 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec P2 33.10 usec NUC1 13C P1 16.55 usec P11 500.00 usec P12 2000.00 usec PL0 120.00 db PL1-0 db SFO1 125.7942548 MHz SP1 2.70 db SP2 2.70 db SPNAM1 Crp60,0.5,20.1 SPNAM2 Crp60comp.4 SPOFF1 0.00 Hz SPOFF2 0.00 Hz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 100.00 usec PL2 1.60 db PL12 24.50 db SFO2 500.2225011 MHz GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ1 30.00 % GPZ2 50.00 % p15 500.00 usec p16 1000.00 usec SI 65536 SF 125.7804117 MHz WDW EM LB 0 Hz PC 0 1D NMR plot parameters CX 22.80 cm CY 3.56 cm F1P 37.000 F1 4653.88 Hz F2P 16.000 F2 2012.49 Hz PPMCM 0.92105 /cm HZCM 115.85038 Hz/cm dept90 36 34 32 30 28 26 24 22 20 18

EXPNO 5 gcosy60 Date_ 20141205 Time 0.30 PULPROG cosygp60.prd TD 2048 NS 4 DS 16 SWH 5000.000 Hz FIDRES 2.441406 Hz AQ 0.2048500 sec RG 5 DW 100.000 usec d0 0.00000300 sec D1 0000000 sec d13 0.00000300 sec IN0 0.00020000 sec SFO1 500.2225000 MHz GPNAM1 sine.100 GPNAM2 sine.100 GPZ1 17.00 % GPZ2 17.00 % P16 1000.00 usec F1 - Acquisition parameters ND0 1 TD 256 SFO1 500.2225 MHz FIDRES 19.531250 Hz SW 9.996 FnMODE undefined 3.0 SI 2048 WDW SINE PC 0 3.5 F1 - Processing parameters SI 1024 MC2 QF WDW SINE 3.5 3.0 2D NMR plot parameters CX2 15.00 cm CX1 15.00 cm F2PLO 4.300 F2LO 2150.95 Hz F2PHI 0.699 F2HI 349.89 Hz F1PLO 4.300 F1LO 2150.95 Hz F1PHI 0.695 F1HI 347.45 Hz F2PPMCM 0.24004 /cm F2HZCM 120.07034 Hz/cm F1PPMCM 0.24036 /cm F1HZCM 120.23310 Hz/cm

gtocsy EXPNO 6 Date_ 20141205 Time 0.52 PULPROG mlevgp_mo TD 2048 NS 8 DS 16 SWH 5000.000 Hz FIDRES 2.441406 Hz AQ 0.2048500 sec RG 5 DW 100.000 usec d0 0.00000300 sec D1 0000000 sec D9 0.10000000 sec d12 0.00002000 sec FACTOR1 7 IN0 0.00020000 sec l1 42 SCALEF 6 p5 23.34 usec P6 35.00 usec p7 70.00 usec P17 2500.00 usec PL10 15.20 db SFO1 500.2225000 MHz GPNAM1 sine.100 GPNAM2 sine.100 GPZ1 10.00 % GPZ2 10.00 % P16 1000.00 usec F1 - Acquisition parameters ND0 1 TD 256 SFO1 500.2225 MHz FIDRES 19.531250 Hz SW 9.996 FnMODE undefined 3.0 SI 2048 SF 500.2200000 MHz WDW SINE PC 1.40 3.5 F1 - Processing parameters SI 1024 MC2 QF SF 500.2200000 MHz WDW SINE 3.5 3.0 2D NMR plot parameters CX2 15.00 cm CX1 15.00 cm F2PLO 4.305 F2LO 2153.32 Hz F2PHI 0.698 F2HI 349.12 Hz F1PLO 4.305 F1LO 2153.32 Hz F1PHI 0.693 F1HI 346.68 Hz F2PPMCM 0.24045 /cm F2HZCM 120.27995 Hz/cm F1PPMCM 0.24078 /cm F1HZCM 120.44271 Hz/cm

ghmqc 25 EXPNO 7 Date_ 20141205 Time 2.12 PULPROG inv4gp.wu TD 2048 NS 8 DS 16 SWH 5000.000 Hz FIDRES 2.441406 Hz AQ 0.2048500 sec RG 5792.6 DW 100.000 usec DE 6.50 usec CNST2 145.0000000 d0 0.00000300 sec D1 0000000 sec d2 0.00344828 sec d12 0.00002000 sec d13 0.00000300 sec d20 0.00242528 sec IN0 0.00001806 sec 50 p2 15.00 usec SFO1 500.2225000 MHz 75 100 ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P3 15.50 usec PCPD2 65.00 usec PL2-0 db PL12 11.30 db SFO2 125.7941690 MHz GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX3 0.00 % GPY3 0.00 % GPZ1 30.00 % GPZ2 18.00 % GPZ3 20 % P16 1000.00 usec 125 150 F1 - Acquisition parameters ND0 2 TD 512 SFO1 125.7942 MHz FIDRES 565742 Hz SW 220.055 FnMODE undefined SI 2048 WDW QSINE PC 1.40 F1 - Processing parameters SI 1024 MC2 QF SF 125.7804117 MHz WDW QSINE SSB 3 3.5 3.0 175 2D NMR plot parameters CX2 18.00 cm CX1 15.00 cm F2PLO 4.300 F2LO 2150.95 Hz F2PHI 0.700 F2HI 350.15 Hz F1PLO 185.028 F1LO 23272.85 Hz F1PHI 14.810 F1HI 1862.81 Hz F2PPMCM 0.20000 /cm F2HZCM 100.04401 Hz/cm F1PPMCM 11.34784 /cm F1HZCM 1427.33569 Hz/cm

ghmqc EXPNO 7 Date_ 20141205 Time 2.12 PULPROG inv4gp.wu TD 2048 NS 8 DS 16 SWH 5000.000 Hz FIDRES 2.441406 Hz AQ 0.2048500 sec RG 5792.6 DW 100.000 usec DE 6.50 usec CNST2 145.0000000 d0 0.00000300 sec D1 0000000 sec d2 0.00344828 sec d12 0.00002000 sec d13 0.00000300 sec d20 0.00242528 sec IN0 0.00001806 sec 20 p2 15.00 usec SFO1 500.2225000 MHz ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P3 15.50 usec PCPD2 65.00 usec PL2-0 db PL12 11.30 db SFO2 125.7941690 MHz 25 GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX3 0.00 % GPY3 0.00 % GPZ1 30.00 % GPZ2 18.00 % GPZ3 20 % P16 1000.00 usec 30 F1 - Acquisition parameters ND0 2 TD 512 SFO1 125.7942 MHz FIDRES 565742 Hz SW 220.055 FnMODE undefined SI 2048 WDW QSINE PC 1.40 35 F1 - Processing parameters SI 1024 MC2 QF SF 125.7804117 MHz WDW QSINE SSB 3 2D NMR plot parameters CX2 18.00 cm CX1 15.00 cm F2PLO 3.000 F2LO 1500.66 Hz F2PHI 0.695 F2HI 347.45 Hz F1PLO 37.162 F1LO 4674.23 Hz F1PHI 15.885 F1HI 1997.98 Hz F2PPMCM 0.12808 /cm F2HZCM 66725 Hz/cm F1PPMCM 1.41848 /cm F1HZCM 178.41696 Hz/cm

ghmbc optimised for 10 Hz couplings 25 EXPNO 8 Date_ 20141205 Time 3.37 PULPROG ghmbc.wu TD 4096 NS 8 DS 16 SWH 5000.000 Hz FIDRES 1.220703 Hz AQ 0.4096500 sec RG 4597.6 DW 100.000 usec CNST2 145.0000000 d0 0.00000300 sec D1 1.25000000 sec d2 0.00344828 sec D6 0.05000000 sec d13 0.00000300 sec IN0 0.00001806 sec 50 p2 15.00 usec SFO1 500.2225000 MHz 75 100 ======== CHANNEL f2 ======== NUC2 13C P3 15.50 usec PL2-0 db SFO2 125.7941690 MHz GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX3 0.00 % GPY3 0.00 % GPZ1 50.00 % GPZ2 30.00 % GPZ3 40.00 % P16 1000.00 usec 125 F1 - Acquisition parameters ND0 2 TD 512 SFO1 125.7942 MHz FIDRES 565742 Hz SW 220.055 FnMODE undefined SI 2048 WDW SINE PC 1.40 150 F1 - Processing parameters SI 1024 MC2 QF SF 125.7804117 MHz WDW SINE 3.5 3.0 175 2D NMR plot parameters CX2 18.00 cm CX1 15.00 cm F2PLO 4.301 F2LO 2151.65 Hz F2PHI 0.699 F2HI 349.89 Hz F1PLO 185.028 F1LO 23272.85 Hz F1PHI 14.810 F1HI 1862.81 Hz F2PPMCM 0.20011 /cm F2HZCM 100.09766 Hz/cm F1PPMCM 11.34784 /cm F1HZCM 1427.33569 Hz/cm

ghmbc optimised for 10 Hz couplings 20 NAME partii_a EXPNO 8 Date_ 20141205 Time 3.37 PULPROG ghmbc.wu TD 4096 NS 8 DS 16 SWH 5000.000 Hz FIDRES 1.220703 Hz AQ 0.4096500 sec RG 4597.6 DW 100.000 usec CNST2 145.0000000 d0 0.00000300 sec D1 1.25000000 sec d2 0.00344828 sec D6 0.05000000 sec d13 0.00000300 sec IN0 0.00001806 sec p2 15.00 usec SFO1 500.2225000 MHz ======== CHANNEL f2 ======== NUC2 13C P3 15.50 usec PL2-0 db SFO2 125.7941690 MHz 25 GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX3 0.00 % GPY3 0.00 % GPZ1 50.00 % GPZ2 30.00 % GPZ3 40.00 % P16 1000.00 usec F1 - Acquisition parameters ND0 2 TD 512 SFO1 125.7942 MHz FIDRES 565742 Hz SW 220.055 FnMODE undefined 30 SI 2048 WDW SINE PC 1.40 F1 - Processing parameters SI 1024 MC2 QF SF 125.7804117 MHz WDW SINE 3.5 3.0 35 2D NMR plot parameters CX2 18.00 cm CX1 15.00 cm F2PLO 4.301 F2LO 2151.65 Hz F2PHI 0.699 F2HI 349.89 Hz F1PLO 37.162 F1LO 4674.23 Hz F1PHI 15.885 F1HI 1997.98 Hz F2PPMCM 0.20011 /cm F2HZCM 100.09766 Hz/cm F1PPMCM 1.41848 /cm F1HZCM 178.41696 Hz/cm

EXPNO 9 gnoesy Date_ 20141205 Time 5.36 PULPROG noesygptp TD 2048 NS 8 DS 16 SWH 5000.000 Hz FIDRES 2.441406 Hz AQ 0.2048500 sec RG 5 DW 100.000 usec D0 0.00000300 sec D1 0000000 sec D8 0.80000001 sec d20 0.39880002 sec IN0 0.00010000 sec 2 P2 15.00 usec SFO1 500.2225000 MHz 4 GPNAM1 sine.100 GPNAM2 sine.100 GPZ1 40.00 % GPZ2-40.00 % P16 1000.00 usec F1 - Acquisition parameters ND0 2 TD 256 SFO1 500.2225 MHz FIDRES 19.531250 Hz SW 9.996 FnMODE undefined 6 SI 2048 WDW QSINE SSB 2 PC 1.40 F1 - Processing parameters SI 1024 MC2 TPPI WDW QSINE SSB 2 8 6 4 2 8 2D NMR plot parameters CX2 15.00 cm CX1 15.00 cm F2PLO 9.000 F2LO 4501.98 Hz F2PHI 0.000 F2HI 0.00 Hz F1PLO 9.000 F1LO 4501.98 Hz F1PHI 0.000 F1HI 0.00 Hz F2PPMCM 0.60000 /cm F2HZCM 300.13202 Hz/cm F1PPMCM 0.60000 /cm F1HZCM 300.13202 Hz/cm

EXPNO 9 gnoesy Date_ 20141205 Time 5.36 PULPROG noesygptp TD 2048 NS 8 DS 16 SWH 5000.000 Hz FIDRES 2.441406 Hz AQ 0.2048500 sec RG 5 DW 100.000 usec D0 0.00000300 sec D1 0000000 sec D8 0.80000001 sec d20 0.39880002 sec IN0 0.00010000 sec P2 15.00 usec SFO1 500.2225000 MHz GPNAM1 sine.100 GPNAM2 sine.100 GPZ1 40.00 % GPZ2-40.00 % P16 1000.00 usec F1 - Acquisition parameters ND0 2 TD 256 SFO1 500.2225 MHz FIDRES 19.531250 Hz SW 9.996 FnMODE undefined 3.0 SI 2048 WDW QSINE SSB 2 PC 1.40 3.5 F1 - Processing parameters SI 1024 MC2 TPPI WDW QSINE SSB 2 3.5 3.0 2D NMR plot parameters CX2 15.00 cm CX1 15.00 cm F2PLO 4.301 F2LO 2151.65 Hz F2PHI 0.699 F2HI 349.89 Hz F1PLO 4.306 F1LO 2159 Hz F1PHI 0.685 F1HI 347 Hz F2PPMCM 0.24013 /cm F2HZCM 120.11719 Hz/cm F1PPMCM 0.24143 /cm F1HZCM 120.76823 Hz/cm

gnoe 3.86112 3.84826 3.84352 3.83163 2.17112 2.15846 2.15685 2.15235 2.14001 2.13774 1.68263 1.66926 1.66097 1.65557 1.64859 1.63568 1.46354 3273 1941 0.88776 NAME partii_a_noe EXPNO 3 Date_ 20141215 Time 21.20 PULPROG gnoe1cc.wu TD 65536 NS 256 DS 8 SWH 10000.000 Hz FIDRES 0.152588 Hz AQ 3.2768500 sec RG 161.3 DW 50.000 usec D1 0000000 sec D8 0.50000000 sec d21 0.33376500 sec d22 0.16399699 sec p2 15.00 usec p3 20 usec p4 30.00 usec p5 20.00 usec P12 40000.00 usec SFO1 500.2207673 MHz SP1 61.60 db SPNAM1 gauss12 SPOFF1 0.00 Hz GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPNAM4 sine.100 GPX3 0.00 % GPX4 0.00 % GPY3 0.00 % GPY4 0.00 % GPZ1 7.00 % GPZ2 3.00 % GPZ3 2.30 % GPZ4-2.30 % P16 1000.00 usec SI 65536 SF 500.2200337 MHz WDW EM LB 0 Hz PC 0 1D NMR plot parameters CX 22.80 cm CY 250.00 cm F1P 4.300 F1 2150.95 Hz F2P 0.700 F2 350.15 Hz PPMCM 0.15789 /cm HZCM 78.98212 Hz/cm 3.5 3.0