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A solid state and solution NMR study of the tautomerism in hydroxyquinoline carboxylic acids

✍ Scribed by Dietrich Gudat; Jacek E. Nycz; Jaroslaw Polanski

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
156 KB
Volume
46
Category
Article
ISSN
0749-1581

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✦ Synopsis

Some hydroxyquinoline carboxylic acids and their conjugate acids and bases were characterized by 13 C and 15 N NMR spectroscopy in solution and in the solid state. Differences in 13 C and, in particular, 15 N chemical shift patterns allow to distinguish between individual tautomers and confirm the presence of zwitterionic species in the solid state. Solution NMR spectra in dimethyl sulfoxide (DMSO) show effects resulting as a consequence of dynamic exchange and suggest the presence of an equilibrium mixture of hydroxyquinoline carboxylic acid and zwitterionic hydroxyquinolinium carboxylate tautomers.

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