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1H and 13C NMR study of 1-substituted isatins and their corresponding 3-(dicyanomethylidene)indol-2-ones

✍ Scribed by Martha S. Morales-Ríos; Pedro Joseph-Nathan

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
340 KB
Volume
29
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The assignments of the ^1^H and ^13^C NMR signals of 1‐substituted isatins and their corresponding 3‐(dicyanomethylidene)indol‐2‐ones were derived by analysis of the ^13^C^1^H spin coupling patterns and by inspection of the two‐dimensional C, H shift correlation spectra. Erroneous literature assignments have been corrected. A significant difference between the ^5^Δ‐deuterium isotope effects on the ^13^C chemical shifts of the CN groups cis and trans to the heterocyclic amide fragment (D)HNCO was observed in partially deuteriated 3‐(dicyanomethylidene)indol‐2‐one. This geometric dependence was used to assign the two CN groups that are otherwise difficult to assign.

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