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Spektrum IR
Spektrum Massa
NMR
The NOESY spectrum confi rms that the methoxy group is located in the vicinity of H-2' and also
shows a strong NOE between H-4 and H-2. The signifi cant cross peaks between the trans olefinnic
protons H-1 and H-2 and the cross peaks between H-4 and H-1 are probably induced by the keto-
enol equilibrium.
APT 13C NMR spectrum at 150 MHz in DMSO-d6
In the carbon NMR spectrum the two obviously assignable signals are from the carbonyl atom C-
3 at 183 ppm and the CH3O group C-7' at 55.7 ppm. Note that the chemical shift value of C-3 is
also indicative for the enolic form.The other CH signals will be easily assigned via the HSQC
spectrum, since the proton assignment is already complete. The remaining three quaternary
carbons will be assigned with the help of the HMBC spectrum. Again, the total number of signals
indicates a symmetric structure.
Expansion of the HSQC spectrum
As the HSQC spectrum reveals, the most shielded olefi nic carbon signal stems from C-4. This is
most likely also caused by the keto enol equilibrium, by which this carbon exchanges with a
methylene group signal. The signals of carbon atoms C-1 and C-2 have the usual order found in
a/b unsaturated ketones.
Expansion of the HMBC spectrum
The HMBC spectrum clarifi es the assignment of the quaternary carbon signals. C-3' at 148 ppm
is seen from the OCH3 protons and from H-5', whereas proton 2' and 6' have a 3J (C,H) spin
coupling to C-4' at 149.4 ppm. C-1' at 126.4 ppm displays the two expected connectivities to H-5'
and H-2. Although no longer needed in this case, C-3 is seen by protons H-1, H-2 and H-4.
Interpretasi NMR