13C and 1H NMR spectroscopic studies on the structure of N‐methyl‐3‐pyridone and 3‐hydroxypyridine

Carbon and proton NMR spectra of 3‐hydroxypyridine and its O‐methyl and N‐methyl derivatives have been analysed, and are compared with the spectra of the corresponding 2‐ and 4‐substituted pyridines. It is shown, that contrary to quantum chemical predictions and in agreement with chemical experience, 3‐hydroxy‐pyridine has a phenolic structure in solution. For the N‐methyl derivative, however, carbon and proton NMR data clearly demonstrate that this compound should be formulated as N‐methyl‐3‐pyridone. The general problem of the 3‐pyridones is discussed on the basis of calculated π‐electron densities, IR and NMR data.