NMRanalyst Sample Application: Strychnine (1 mg)

Strychnine (1 mg)
NMRanalyst Sample Application

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Sample Description:

Molecular Formula: C₂₁H₂₂N₂O₂
Molecular Weight: 334.412

InChI=

1/C21H22N2O2/c24-18-10-16-19-13-9-17-21(6-7-22(17)11-12(13)5-8-
25-16)14-3-1-2-4-15(14)23(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2

IUPAC Name:

Strychnidin-10-one

CAS Number: 57-24-9
PubChem: 5304
NMRShiftDB: 10009153
Spectrometer: Varian INOVA 500 MHz
Solvent: CDCl₃
Sample Concentration: 1 mg (3 micromole)

Provided by:

Dr. Igor Goljer, Varian Inc.

*.fid/text file specifies: 1mg of Strychnine in 40 ul of CDCl3 in gHX Nanoprobe
*.fid	np	nt	sw	rfp-rfl	ni	sw1	rfp1-rfl1	time

proton	39700	4	6060.61	-653.81				21 s
carbon	65484	4000	31446.54	-1899.08				1 h 16 m
gHMBC	2048	4	6060.61	-546.61	600	30165.91	-1887.14	1 h 3 m
gHSQC	2048	2	6060.61	-546.61	256	21361.82	-1255.32	27 m 4 s
gDQFCOSY	2048	2	6060.61	-653.81	400	6060.61	-653.81	41 m 19 s
N15_gHMBC	2048	64	6060.61	-653.81	48	10129.15	-0.17	1 h 19 m

1D Proton Spectrum:

1D Carbon Spectrum (Deuterated Solvent Resonances Subtracted):

Automated VerifyIt Proton Assignments:

Automated VerifyIt Carbon Assignments:

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

The correct structure is at position 1.


 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.959858 (    5304)    2: 0.955641 ( 5318675)    3: 0.955641 ( 5907745)
    4: 0.954045 (  276141)    5: 0.939271 ( 9509473)    6: 0.935556 ( 9369669)
    7: 0.935045 ( 8588845)    8: 0.934462 (  848361)    9: 0.934124 ( 9371247)
   10: 0.933272 ( 8748549)

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

The correct structure is at position 1.


 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.948742 (    5304)    2: 0.937532 ( 5390635)    3: 0.925595 ( 3041794)
    4: 0.922690 ( 5147783)    5: 0.918983 ( 3041789)    6: 0.912186 (  211181)
    7: 0.908455 ( 5378955)    8: 0.907726 (  101682)    9: 0.906988 (  102382)
   10: 0.901606 ( 2057133)

2D Multiplicity-Edited HSQC Spectrum:

Determined HSQC Correlations:

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

The correct structure is at position 1.


 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.948742 (    5304)    2: 0.937532 ( 5390635)    3: 0.925595 ( 3041794)
    4: 0.922690 ( 5147783)    5: 0.918983 ( 3041789)    6: 0.912186 (  211181)
    7: 0.908455 ( 5378955)    8: 0.907726 (  101682)    9: 0.906988 (  102382)
   10: 0.901606 ( 2057133)

2D DQF-COSY Spectrum:

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

AssembleIt HSQC & DQF-COSY Derived Correlations

2D N15_HMBC Spectrum:

AssembleIt HSQC & N15_HMBC Derived Nitrogen-Carbon Correlations:

AssembleIt HSQC & N15_HMBC Derived Correlations

2D HMBC Spectrum:

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

AssembleIt Derived Structure With NMRgraph Added Likely Oxygen Atoms:

Most likely structure (out of 2 possible ones) by agreement with carbon chemical shift prediction

Comments:

Strychnine is used as a bird, mammal, and insect control agent.

FindIt identifies the correct structure at place one.

Spectroscopists strive to acquire perfectly looking NMR spectra. But from a practical point of view, the structure elucidation goal is to determine the structure from a limited amount of sample in a reasonable amount of time. This 1 mg strychnine example is a step in this direction. Not all shown spectra have a perfect appearance. Our point is that these datasets are adequate for the NMRanalyst structure elucidation.

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