Brucine
NMRanalyst Sample Application
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Sample Description:

 Molecular Formula: C23H26N2O4
Molecular Weight: 394.464
InChI= 1/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-
23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-
11H2,1-2H3/t13?,18?,19?,21?,22?,23-/m1/s1
IUPAC Name:  2,3-Dimethoxystrychnidin-10-one
CAS Number: 357-57-3
PubChem: 9649
NMRShiftDB: 20042191
Spectrometer: Varian INOVA 500 MHz
Solvent: CDCl3
Sample Concentration: 5 mg
Provided by:  Dr. Dimitris Argyropoulos, Varian Deutschland GmbH

*.fid/text file specifies: Brucine... | 5 mg in CDCl3
*.fidnpntswrfp-rflnisw1rfp1-rfl1time
PROTON1770044668.53-66.0817 s
CARBON78460819230165.91-1258.347 h 31 m
DQFCOSY204824668.53-66.085124668.53-66.081 h 2 m
gHMBC204884668.53-66.0851228905.9902 h 3 m
gHSQC102444668.53-66.0825620110.61-1.0545 m 34 s
N15-gHMBC2048324668.53-66.081282025.824558.102 h 4 m


1D Proton Spectrum:

1D Proton Spectrum


1D Carbon Spectrum (Deuterated Solvent Resonances Subtracted):

1D Carbon Spectrum


 

Automated VerifyIt Proton Assignments:

Proton Assignments
 

Automated VerifyIt Carbon Assignments:

Carbon Assignments

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

The correct structure is at position 4.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.955525 (  220197)    2: 0.954765 (  276140)    3: 0.954085 (  220518)
    4: 0.953171 (    9649)    5: 0.949960 ( 3081763)    6: 0.949960 ( 5318514)
    7: 0.947528 (  633831)    8: 0.943049 ( 5319456)    9: 0.930901 ( 8394774)
   10: 0.929926 ( 8394719)
			

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

The correct structure is at position 1.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.918970 (    9649)    2: 0.907258 (  458085)    3: 0.886418 (  161215)
    4: 0.884381 ( 5147853)    5: 0.880259 (  276140)    6: 0.879185 ( 6978343)
    7: 0.875640 (  220518)    8: 0.875138 (  220197)    9: 0.874196 (  275193)
   10: 0.865935 (  651999)
			

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: 0.940963 (    9649)    2: 0.899355 (  264628)    3: 0.897448 (  220518)
    4: 0.893673 (  220197)    5: 0.892549 (  161215)    6: 0.891888 (  276140)
    7: 0.886883 (  253039)    8: 0.886714 (  458085)    9: 0.885339 ( 6978343)
   10: 0.885164 ( 3199155)
			

2D DQF-COSY Spectrum:

2D DQF-COSY Spectrum

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

AssembleIt HSQC & DQF-COSY Derived Correlations

Entered HSQC & N15_HMBC Nitrogen-Carbon Correlations:

Entered HSQC & N15_HMBC 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 109 possible ones) by agreement with carbon chemical shift prediction

Comments:

Brucine is used as a denaturant in oils and alcohols, particularly in cosmetic preparations. It is also used in analytical chemistry for separating racemic mixtures.

The 15N resonance linewidths are over 20 Hz wide. Hence the acquisition of a large number of F1 resonances for the N15 HMBC causes an unacceptably low S/N. Furthermore, the acquired 90 to 129.8 ppm F1 sweep width does not contain the 37.00 or 151.0 ppm nitrogens of brucine. Fortunately, the strychnine (1mg) dataset has a similar molecular structure as brucine. So the observed strychnine N15 HMBC correlations with carbon shifts adjusted for the brucine carbons are used for this structure elucidation.

FindIt identifies the correct structure as the top one using proton and carbon, as well as proton and protonated carbon information.


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