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Considering a Pyridinone Fragment

Chemical shift information offers a clue into an atom’s hybridization state. For example, carbon atoms with a carbon chemical shift greater than 90 ppm are typically considered as sp2 carbons. If 4 sp2 carbons are present, one can infer 2 alkene pairs. Five sp2 carbons and an available oxygen and nitrogen atom suggest the possibility of a pyridinone fragment.

The example below shows a 5 sp2 carbons and 2 sp3 carbons, coloured pink and blue, respectively. The chemical shift at 167 ppm for the quaternary carbon suggests the presence of an amide group.

NCORing_1_Apr142009

Using the information described above, a set of 6 possible candidate structures can be pieced together.

NCORing_2Str_Apr142009