15 N NMR studies of the tautomeric equilibrium of some 1‐hydroxybenzotriazoles | Zendy

Schilf W. | Zendy; Stefaniak L. | Zendy; Witanowski M. | Zendy; Webb G. A. | Zendy

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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

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.

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