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Magnetic non-equivalence in N,N-diethylbenzamides and -thiobenzamides conformation of the N-alkyl groups

✍ Scribed by Ulf Berg; Jan Sandström

Publisher
Elsevier Science
Year
1976
Tongue
French
Weight
238 KB
Volume
17
Category
Article
ISSN
0040-4039

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✦ Synopsis

Two different rationalizations of magnetic non-equivalence of geminal methylene protons in ortho substituted N,N-diethylbenzamides and related compounds have been advanced. Bedford et ',';;T -* and more recently Fulea and Krueger' advocate a "conformational effect", whereas Siddall and Garner3 and Lewin et. 495 see hindered rotation of the aryl group as the reason for the non-equivalence, The controversy can be simplified as follows. According to Siddall et al. 3,6 and Lewin et al. 495 the aromatic ring and the (thio)amide group are more or less orthogonal.

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