Penentuan Struktur Curcumin

Spektrum IR
Spektrum Massa
 NMR

1H NMR spectrum at 600 MHz in DMSO-d6

 Expansion of the DQF-COSY spectrum
The spin couplings described are nicely revealed also in the COSY spectrum. To display the cross
peaks for the small spin coupling between H-2' and H-6' would cause an overflow for the other
signals; however, these cross peaks can be easily observed on a computer screen or enhanced by
using long-range COSY.
 NOESY spectrum
In the NOESY spectrum all signals have the same sign as the diagonal, therefore they are printed
here with the same colour. For a molecule of this size this is unusual, even in DMSO solution. An
explanation for this is an ongoing keto-enol equilibrium, where normal NMR detects only the
predominant enol form, but NOESY is able to detect the exchange by the sign of the cross peaks.

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