Codeine was selected as a test sample to illustrate the application of different NMR experiments to structure determination and assignment, and to compare various versions of each experiment.
C18H21NO3, MW= 299.4
NMR samples used were between 3 and 18 mg, in .65ml CDCl3 with TMS, run on a JEOL Eclipse+ 400 spectrometer.
Interactive view - Those who have installed the Chime plug-in can view and manipulate the codeine structure in 3D, examine and expand the 1H spectrum, and interactively correlate 1H peaks with H atoms in the structure. This page also includes detailed description of how to display structures and spectra interactively using Chime.
MDL has finally modified the plug-in
to work with IE 6. This new version is 2.6 sp 4.
Each experiment is described, along with acquisition and processing parameters, and spectra are shown with assignment of all peaks. For readers interested in the details of data acquisition, several good books are available.
See table of assignments and assignment strategy.
Experiments:
1D 1H and 13C
DEPT and APT
COSY
TOCSY
NOESY
HMQC
HMBC
HMQC-TOCSY
HSQC-NOESY
INADEQUATE
In the course of acquiring and processing these data, some observations were made, including:
comparison of HMQC and HSQC
choice of processing parameters for HMQC (window function and magnitude vs. power spectrum)
comparison of HMBC spectra run on 3 mg sample and 18 mg sample
Most fids for the experiments listed above are available for download. Individual files are listed below, or download zip files of fids (6.3 Mbytes) or all files (fids and spectra, 20.4 Mbytes).
1H
13C
DEPT-45, DEPT-90 and DEPT-135
APT
COSY
TOCSY
NOESY
HMQC, HSQC, HSQC-DEPT
HMBC of 3 mg sample and 18 mg sample (optimized for 8 Hz)
HMBC of 8 mg sample optimized for 4 Hz couplings
HMQC-TOCSY
Processed data are also available for download:
Last updated: 12/06/2005
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