P660: Thematic use of ribavirin as an example to illustrate NMR principles and techniques
Ribavirin is a molecule used clinically to treat viral infections. It has a number of structural features that make it an ideal example for illustrating a variety of NMR principles and instrumental techniques. Ribavirin was used in a thematic fashion as a recurring example throughout a semester-long interpretative spectroscopy course to introduce concepts that started with the simple and progressed toward the complex. Examples included: 1) molecular asymmetry and number of signals, 2) diastereotopic methylene proton signals, 3) observing spin-spin splitting between hydroxyl protons and neighboring protons, 4) proton-deuterium exchange experiments with hydroxyl group protons, 5) 1D selective decoupling experiments to assign proton signals, 6) 1D-NOE experiments, 7) temperature-dependent NMR experiments to study amide bond rotation, 8) homonuclear 2-D correlation experiments including COSY and NOESY, 9) heteronuclear 2-D correlation experiments including HETCOR, HMQC, or HSQC for short range C-H correlations, and FLOCK or HMBC for long range C-H correlations.