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13C NMR of methyl N-methylthiobenzimidates. A novel approach to the interpretation of the relative 13C-E/Z shifts in amides and related compounds

✍ Scribed by Wolfgang Walter; Wulf Ruback; Claus O. Meese

Book ID
102527347
Publisher
John Wiley and Sons
Year
1978
Tongue
English
Weight
458 KB
Volume
11
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^13^C NMR shifts of the E/Z mixtures of twelve, mainly ortho substituted, methyl N‐methylthio‐benzimidates have been completely assigned. The angles of twist about the aryl‐imino‐carbon bond were determined by means of the C‐1 aryl shifts. Depending on the bulk of the ortho substituents the values vary from 18° in methyl 2‐fluoro‐N‐methylthiobenzibenzimidate (Z) to 73° in methyl 4‐bromo‐N,2,6‐trimethylthio‐benzimidate (E). An explanation for the ^13^C‐E/Z‐N‐alkyl and ‐S‐alkyl resonances is facilitated by a new model which is initially based on the influence of electric fields. As this model is derived from amides, thioamides etc. it is possible to interpret the ^13^C‐E/Z shifts in all related classes of compounds. The role of steric compression does not seem to be as important as was previously assumed.

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