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Will the correct structure please stand up? … Part 1

April 28, 2010

Many organic chemists—if not all—check to see if a synthetic reaction is complete via TLC and LC/MS and/or 1H NMR. At the same time, the chemists are using the analytical data to verify that the final product is what they intended on making. In some cases, LC/MS and 1H NMR do not adequately distinguish one potential product from another. It then becomes a question of identifying a technique(s) that can clearly verify the correct product.

The chemical structures shown below (3-methyl-5-(pyridin-2-yloxy)pyridine and 5′-methyl-2H-1,3′-bipyridin-2-one) are two possible products for a synthetic reaction. They have an identical formula weight (FW) and a nearly identical MS and 1H NMR (not shown). What other experiments can a chemist/spectroscopist propose that will assist in identifying the correct structure and thus distinguish the ester from the carbonyl product?

RightStructureByNMR_1_Apr272010

I would like to give a special thanks to David C. Adams for proposing the idea.

One Reply to “Will the correct structure please stand up? … Part 1”

  1. Easy, FT-IR!..the only reason why this technique is still used..you can see CO vibrations at 1600-1700 cm-1

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