INTRA-MOLECULAR CHARGE RELAY SYSTEM VIA EASILY POLARIZABLE HYDROGEN-BONDS IN THE N-(4-METHYL-2-PYRIDYL)AMIDE OF 6-METHYLPICOLINIC ACID N-OXIDE

The N-(pyridyl)amides 2,3, and 4 were studied in chloroform-d1 solution by IR spectroscopy. Similar to anilides 1 these compounds show a broad NH stretching vibration demonstrating the formation of an intramolecular asymmetrical hydrogen bond with the proton at the amide group. The perchlorates of these compounds, 5, 6, and 7, were studied in acetonitrile-d3. With compound 6 the two intramolecular hydrogen bonds are easily polarizable proton transfer hydrogen bonds. The proton fluctuates in these bonds. An intramolecular charge relay system is present in this molecule. © 1979 American Chemical Society.