3-(4-Methoxyphenyl)cyclopent-2-en-1-one
NMRanalyst Sample Application
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Sample Description:

 Molecular Formula: C12H12O2
Molecular Weight: 188.222
InChI= 1/C12H12O2/c1-14-12-6-3-9(4-7-12)10-2-5-11(13)8-10/h3-4,6-8H,2,5H2,1H3
IUPAC Name:  3-(4-Methoxyphenyl)cyclopent-2-en-1-one
Spectrometer: Bruker 300 MHz
Solvent: CDCl3
Sample Concentration: 50.6 mg
Provided by:  Prof. Charles G. Fry, University of Wisconsin - Madison, Fall 2002.

DirectorynpF2NSswF2spF2npF1swF1spF1time
proton16384326024.096-1214.8801 m 59 s
carbon3276819220833.334-2116.69514 m 38 s
DEPT-1353276819220833.334-2116.69511 m 26 s


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 1.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.968427 (      U4)    2: 0.957129 ( 7172141)    3: 0.953478 (  575313)
    4: 0.952935 (  575582)    5: 0.948196 (  140335)    6: 0.947380 (  575048)
    7: 0.946346 (  223388)    8: 0.946084 (  223159)    9: 0.945333 ( 2776433)
   10: 0.943433 ( 6071028)
			

Top 15 FindIt Molecular Structures Consistent With Proton and Carbon Resonances:

The correct structure is at position 13.

FindIt Structures

 Best 15 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.905364 (  772073)    2: 0.904735 ( 3846895)    3: 0.890776 (   76613)
    4: 0.887010 (  155971)    5: 0.886106 ( 6497069)    6: 0.880894 ( 2434818)
    7: 0.872585 (  819922)    8: 0.871080 (  786180)    9: 0.870480 ( 2759694)
   10: 0.870174 (  742746)   11: 0.869857 (  748854)   12: 0.867412 ( 4987769)
   13: 0.867000 (      U4)   14: 0.864677 ( 6497068)   15: 0.864320 ( 4220925)
			

DEPT-135 Spectrum:

DEPT-135 Spectrum

Top 10 FindIt Molecular Structures Consistent With Proton and Protonated Carbon (DEPT-135) Resonances:

The correct structure is at position 10.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.950013 ( 4745197)    2: 0.948878 ( 2147132)    3: 0.947003 ( 9484218)
    4: 0.946558 ( 8258891)    5: 0.943479 (  690622)    6: 0.942831 ( 3100995)
    7: 0.942385 ( 6472748)    8: 0.941939 ( 3298737)    9: 0.940644 (  689155)
   10: 0.940591 (      U4)
			

Comments:

The likely carbon shift assignments for this molecule are shown. The 161.98, 126.59, 173.49, and 209.11 ppm carbons don't appear in the DEPT-135 spectrum and are known to be unprotonated. The 28.47 and 35.10 ppm carbons are negative in the DEPT-135 belonging to CH2 groups. The FindIt rating using the carbon spectrum is less than perfect. But with additional molecular formula, the correct structure obtains place one.


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