Verbenol
NMRanalyst Sample Application
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Sample Description:

 Molecular Formula: C10H16O
Molecular Weight: 152.233
InChI= 1/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3
IUPAC Name:  4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol
CAS Number: 18881-04-4
PubChem: 61126
NMRShiftDB: 10021322
Spectrometer: Varian INOVA 500 MHz
Solvent: CDCl3
Sample Concentration: 49 mg for 1D carbon, 8 mg for other spectra
Provided by:  Dr. Charles L. Mayne, University of Utah

*.fidnpntswrfp-rflnisw1rfp1-rfl1time
proton1600001610000-2503.712 m 43 s
carbon524288100000050000-16647.0222 m 2 s
hmbc819284366.10-414.46102425000-4314.1031 h 57 m
hmqc204884366.10-413.8151225000-1830.5618 h 36 m


1D Proton Spectrum:

1D Proton Spectrum


1D Carbon Spectrum (Deuterated Solvent and TMS 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 1.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.964759 (   61126)    2: 0.963595 (  527032)    3: 0.963285 ( 6428927)
    4: 0.961481 (  349147)    5: 0.960085 (  576906)    6: 0.959715 (  170304)
    7: 0.959690 (  520984)    8: 0.958384 ( 6428796)    9: 0.957570 (   62842)
   10: 0.957196 (  561871)
			

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

The correct structure is at position 3.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.915841 ( 6428927)    2: 0.905663 (  527032)    3: 0.902126 (   61126)
    4: 0.891130 (  573227)    5: 0.883639 (  249596)    6: 0.883551 ( 6365962)
    7: 0.880624 (  557576)    8: 0.869403 (  349147)    9: 0.868830 ( 6430778)
   10: 0.867749 (  590302)
			

2D HMQC Spectrum:

2D HMQC Spectrum

Determined HMQC Correlations:

Determined HMQC Correlations

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

The correct structure is at position 1.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.912314 (   61126)    2: 0.910734 (  527032)    3: 0.907350 (  162747)
    4: 0.896619 (  118088)    5: 0.894939 ( 8028799)    6: 0.894329 ( 7332995)
    7: 0.889530 (  557576)    8: 0.888102 ( 8447365)    9: 0.886796 ( 9903146)
   10: 0.886505 (  102553)
			

2D Phase Sensitive HMBC Spectrum:

2D HMBC Spectrum

AssembleIt HSQC (HMQC) & HMBC Derived Carbon-Carbon Correlations:

AssembleIt Derived Correlations

AssembleIt Derived Structure With NMRgraph Added Likely Oxygen Atoms:

AssembleIt Derived Structure   Most likely structure (out of 5 possible ones) by agreement with carbon chemical shift prediction

Comments:

Verbenol is a monoterpenoid pheromone.

This was our first structure elucidated using indirect detection spectra. Since 1999, we have considerably improved this approach.

NMRanalyst supports twelve spectrum types. The verbenol HMQC spectrum is analyzed using NMRanalyst's HSQC spectrum type. The HMQC spectrum was acquired without multiplicity editing. If NMRanalyst does not consider multiplicity editing, HSQC detected carbons are shown as CH groups (three free valences). This results in thousands of verbenol structures. But the carbon shift agreement still identifies the correct one.

Here NMRanalyst is instructed to assume HSQC multiplicity editing. Without observed negative HSQC correlations, no carbons are reported as CH2. But likely CH3 carbons are identified. Multiplicity editing should be used for the acquisition of all HSQC spectra. It is faster to acquire than a 1D DEPT spectrum and simplifies the structure elucidation.

The verbenol HMBC spectrum shows prominent T1 ridges. Today such spectra are preferably acquired using Pulse Field Gradients (PFG) as shown by the other demo datasets.


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