Quinine
NMRanalyst Sample Application
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Sample Description:

 Molecular Formula: C20H24N2O2
Molecular Weight: 324.417
InChI= 1/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-
15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3
IUPAC Name:  6'-Methoxycinchonan-9-ol
CAS Number: 56-54-2
PubChem: 1065
NMRShiftDB: 10016314
Spectrometer: Bruker AV 400 MHz
Probe: 1mm MicroProbe
Solvent: CDCl3
Sample Concentration: ca. 200 µg
Provided by:  Dr. Till Kühn, Bruker BioSpin

DirectorynpF2NSswF2spF2npF1swF1spF1time
proton (300)32768328802.82-2382.523 m 35 s
gDQF-COSY (301)102423591.95105.765123591.95105.761 h 26 m
gHSQC (302)1024124006.41-101.4725616666.67-829.602 h 32 m
gHMBC (303)1024403591.95105.7651223148.15-1529.2910 h 28 m
N15-gHMBC (305)102420484006.4115.851616220.60-2028.5818 h 18 m


1D Proton Spectrum:

1D Proton Spectrum


Top 10 FindIt Molecular Structures Consistent With Molecular Formula and Proton Resonances:

The correct structure is at position 7.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.957622 (  102439)    2: 0.957340 ( 3499717)    3: 0.955644 (   65753)
    4: 0.955078 (  847715)    5: 0.953062 ( 6336167)    6: 0.953047 (  585971)
    7: 0.952892 (    1065)    8: 0.950814 (    8547)    9: 0.949068 (  934598)
   10: 0.948731 ( 2037943)
			

2D Multiplicity-Edited HSQC Spectrum:

2D Multiplicity-Edited HSQC Spectrum

Determined HSQC Correlations:

Determined HSQC Correlations

Top 10 FindIt Molecular Structures Consistent With Proton and Protonated Carbon (HSQC) Resonances:

The correct structure is at position 1.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.937466 (    1065)    2: 0.915501 ( 6336167)    3: 0.900599 ( 3499717)
    4: 0.897815 (  183259)    5: 0.895740 ( 3083557)    6: 0.894629 (  101764)
    7: 0.894536 (   84495)    8: 0.891677 ( 4835740)    9: 0.890939 ( 3809868)
   10: 0.889296 ( 5191849)
			
 

Automated VerifyIt Proton Assignments:

Proton Assignments
 

Automated VerifyIt Carbon Assignments:

Carbon Assignments

2D DQF-COSY Spectrum:

2D DQF-COSY Spectrum

AssembleIt HSQC & DQF-COSY Derived Carbon-Carbon Correlations:

AssembleIt HSQC & DQF-COSY Derived Correlations

2D N15_HMBC Spectrum:

2D N15_HMBC Spectrum

AssembleIt HSQC & N15_HMBC Derived Nitrogen-Carbon Correlations:

AssembleIt HSQC & N15_HMBC Derived Correlations

2D HMBC Spectrum:

2D HMBC Spectrum

AssembleIt HSQC, HMBC, DQF-COSY & N15_HMBC Derived Correlations:

AssembleIt Derived Correlations

AssembleIt Derived Structure With NMRgraph Added Likely Oxygen Atoms:

AssembleIt Derived Structure   Most likely structure (out of 277 possible ones) by agreement with carbon chemical shift prediction

Comments:

Quinine is used as an antimalaria drug.

Before performing a full structure elucidation, consider running FindIt. Only the molecular formula, proton, and/or (potentially only protonated) carbon shift information are needed.

At natural abundance, a 1D carbon spectrum is 5,700 times less sensitive to acquire than a 1D proton spectrum. Acquiring the shown HSQC and HMBC spectra instead is still faster than acquiring one 1D carbon spectrum. The full quinine structure elucidation is demonstrated using about 200 micro grams of sample. Only the shown NMR data from a room-temperature 1 mm capillary probe are used. No molecular formula (MF) or information from other spectroscopic methods are needed.


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