C8953
NMR structural analysis
seminar
Elucidenting the structure using variouse NMR techniques
Jan Novotný
176003@mail.muni.cz
May 10, 2017
Isomerisms and NMR
� Functional groups (constitution) - chemical shift
� Position of substituents - HMBC, NOESY/ROESY
� Relative configuration on double bonds or rings J-coupling,
NOESY/ROESY
� Absolute configuration - application of Chiral Derivatizing
Agents (CDA)
Benzothiazole Biodegradation: 1H-15N HMBC (Appl. Environ. Microbiol., 2001, 67)
Determine the structure of C10H18O using
INADEQUATE exp.
Regioselectivity in the Halogenation: 1,1-ADEQUATE (Org. Lett., 2016, 18, 19561959)
X = O X = S
Configuration on double bonds (Magn. Reson. Chem.
2008, 46, 872–877)
Describe the isomers of molecule shown bellow:
Configuration on double bonds (Magn. Reson. Chem.
2008, 46, 872–877)
Describe the isomers of molecule shown bellow:
Configuration on double bonds: NOESY
Relative stereochemistry on a ring: NOESY
Provide the complete assignment of 1
H resonances and determine
the orientation of H5 and H6.
Interpretation of J-coupling
Unknown compound C6H12O6 measured in D2O
Detected JHH-couplings: (2x9.6), (2.8, 9.6), (2x9.6), (2x2.8)
4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2
Chemical Shift (ppm)
1.02.02.11.0
1 2 3 4
1D 13
C NMR spectrum contains 4 signals in the range 71-75 ppm.