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Tautomerism in 2-hydroxy-1-naphthaldehyde schiff bases in solution and the solid state investigated using 13C NMR spectroscopy

✍ Scribed by S. R. Salman; J. C. Lindon; R. D. Farrant; T. A. Carpenter

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
282 KB
Volume
31
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^13^C and ^1^H NMR spectra of six Schiff bases formed from 2‐hydroxy‐1‐naphthaldehyde and substituted anilines were measured and assigned in a variety of solvents. Based on the ^13^C chemical shifts and ^3^J(CH,NH), the ratio of the keto‐amine and phenol‐imine tautomers was derived using both ^13^C chemical shifts and ^1^H−^1^H coupling constants, the two methods giving comparable results. The solid‐state ^13^C NMR spectra of two of these Schiff bases were also measured and interpreted. Based on chemical shift assignments from solution NMR, which showed a relationship between certain shifts and the proportions of the tautomers, it has been shown that these compounds exist essentially as the keto‐amine form in the solid, the tautomer previously shown to be the more thermodynamically stable.

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