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15 N NMR studies of the tautomeric equilibrium of some 1‐hydroxybenzotriazoles
Author(s) -
Schilf W.,
Stefaniak L.,
Witanowski M.,
Webb G. A.
Publication year - 1985
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.1260230310
Subject(s) - tautomer , chemistry , intramolecular force , solvent , proton nmr , hydrogen , computational chemistry , equilibrium constant , hydrogen bond , medicinal chemistry , stereochemistry , organic chemistry , molecule
Abstract By means of 15 N NMR shielding measurements it is possible to obtain quantitative results on tautomeric equilibria for N ‐hydroxybenzotriazole and its 4‐ and 6‐mononitro derivatives. For the unsubstituted compound the position of the tautomeric equilibrium is found to depend on the p K a value of the solvent. Intramolecular hydrogen bonding appears to be responsible for an increase in the proportion of the N ‐oxide form present in the equilibrium mixture of the 4‐mononitro compound.