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13 C and 15 N NMR investigation of the prototropic equilibrium of 2‐hydroxy‐3‐methylindazole
Author(s) -
Schilf W.,
Stefaniak L.,
Webb G. A.
Publication year - 1987
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260250812
Subject(s) - chemistry , pyridine , pyrrole , solvent , carbon 13 nmr , nuclear magnetic resonance spectroscopy , chemical shift , solvent effects , computational chemistry , stereochemistry , medicinal chemistry , organic chemistry
Abstract It is shown that both 13 C and 15 N NMR measurements provide similar estimates of the position of the prototropic equilibrium exhibited by 2‐hydroxy‐3‐methylindazole in three solvents. The 15 N NMR study of the pyridine and pyrrole types of nitrogen atoms provided the most quantitatively reliable results. The position of the prototropic equilibrium was found to be critically dependent on the acidity of the chosen solvent, the quinonoid form being predominant in weakly acidic media.