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Saturday, 20 December 2014

VERBENOL

VERBENOL

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: 8 mg

structure of trans-Verbenol

Properties calculated from structure

PropertyValue?
FormulaC10H16O
Weight152.233 [g/mol]
Complexity214.91
XLogP2.12
TPSA20.23
#HDonors1
#HAcceptors1
Gibbs Energy-42.9 [kcal/mol]
1H NMR spectrumPredict NMR spectrum (requires installed Java plugin)
Predict NMR spectrum (requires HTML5 compatible browser)
13C NMR spectrumPredict NMR spectrum (requires HTML5 compatible browser)
Isotopic distributionPredict Isotopic distribution

1D Proton Spectrum (TMS Resonances Subtracted):

1D Proton Spectrum


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: 0.892462 (   61126)    2: 0.792875 (  421322)    3: 0.786969 (  118088)
    4: 0.782868 (  433073)    5: 0.782421 (  556905)    6: 0.776775 (  247518)
    7: 0.775072 (  282018)    8: 0.774000 (   72421)    9: 0.773790 (   91238)
   10: 0.773789 (  247514)

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 4 possible ones) by agreement with carbon chemical shift prediction

MASS SPECTRUM

Comments:

Verbenol is a monoterpenoid pheromone.
The verbenol datasets were our first application of using indirect detection spectra. We used to base structure elucidations on a 1D carbon and a 2D INADEQUATE spectrum. Indirect detection methods gain an order of magnitude in sensitivity. But we continued to use the 1D carbon spectrum which is the least sensitive spectrum by now. Eliminating it completes our goal of indirect detection. Several insights result:
It greatly simplifies the structure elucidation when all spectra are acquired with consistent referencing (not the case for this sample). The next best approach is to use the 1D carbon spectrum to adjust the carbon referencing of all spectra. Here it was necessary to use the exhaustive HSQC and HMBC F1 mapping results for referencing corrections. This is tedious and acquiring datasets with consistent referencing is preferable.

Strong ridges at the TMS (0 ppm) and the three methyl carbon frequencies show in the regular HMBC. Adjustment of the single "Ridge" parameter excludes ridge misinterpretations as shown. It would be preferable to acquire this spectrum with Pulse Field Gradient support to simplify the spectral analysis.






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