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13 C and 1 H NMR spectroscopic studies on the structure of N‐methyl‐3‐pyridone and 3‐hydroxypyridine
Author(s) -
Vögeli U.,
von Philipsborn W.
Publication year - 1973
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270051202
Subject(s) - 2 pyridone , chemistry , carbon 13 nmr , proton , chemical shift , spectral line , pyridine , carbon 13 nmr satellite , proton nmr , quantum chemical , derivative (finance) , nuclear magnetic resonance spectroscopy , crystallography , medicinal chemistry , stereochemistry , molecule , fluorine 19 nmr , organic chemistry , physics , quantum mechanics , astronomy , financial economics , economics
Abstract 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.