Sample Description:

Molecular Formula: C10H20O Molecular Weight: 156.265 InChI= 1/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3 IUPAC Name:  2-Isopropyl-5-methylcyclohexanol CAS Number: 89-78-1 PubChem: 1254 NMRShiftDB: 10008950 Spectrometer: Varian INOVA 500 MHz Solvent: CDCl3 Sample Concentration: 2 mg Applications: Topical analgesic and antipruritic Provided by:  Dr. Dimitris Argyropoulos, Varian Deutschland GmbH

*.fid/text file specifies: Menthol... 2 mg in CDCl3
*.fid	np	nt	sw	rfp-rfl	ni	sw1	rfp1-rfl1	time
PROTON	8722	4	2302.29	-66.76				17 s
CARBON	32768	8192	12588.51	-10.34				5 h 14 m
gDQF-COSY	1024	2	2302.82	-67.03	256	2302.29	-66.76	31 m
gHMBC	1024	8	2302.82	-67.03	256	12567.82	0	59 m
gHSQC	920	2	2302.82	-67.03	256	12566.76	0.53	25 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 8.

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.980098 (  549904)    2: 0.978656 (  228304)    3: 0.978113 (  220207)
    4: 0.977428 (  118129)    5: 0.976737 (  574674)    6: 0.976361 (   62350)
    7: 0.976332 ( 1797950)    8: 0.976110 (    1254)    9: 0.974860 (  545293)
   10: 0.974712 (   91338)
			

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: 0.944837 (    1254)    2: 0.926940 ( 1597048)    3: 0.920149 ( 4418301)
    4: 0.919076 (   86798)    5: 0.918728 ( 6454875)    6: 0.917544 (   56224)
    7: 0.915304 (  375777)    8: 0.914156 (  558050)    9: 0.913513 ( 1636096)
   10: 0.912965 (  560763)
			

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: 0.943527 (    1254)    2: 0.938413 (  558259)    3: 0.935518 ( 1391551)
    4: 0.932191 (  360318)    5: 0.929882 (  520673)    6: 0.929349 ( 2755306)
    7: 0.927448 (  586745)    8: 0.926733 (  235854)    9: 0.924183 ( 1597048)
   10: 0.922191 (  583664)
			

2D DQF-COSY Spectrum:

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

2D HMBC Spectrum:

AssembleIt HSQC, HMBC & DQF-COSY Derived Correlations:

AssembleIt Derived Structure With NMRgraph Added Likely Oxygen Atoms:

Most likely structure (out of 4 possible ones) by agreement with carbon chemical shift prediction

Comments:

For FindIt, the correct structure is identified using proton and carbon, as well as proton and protonated carbon analysis results.

For the complete structure elucidation, the challenge are three proton frequencies (1.004, 0.955, 0.939 ppm) correlating in the HSQC with two carbons each. See the shown HSQC expansion. Ambiguities detected in the assignments of DQF-COSY and HSQC correlations are communicated to the structure generation. So all structures in agreement with ambiguous assignments are duly considered.