Investigation of the amide rotation in  N , N ‐dialkylbenzamides. 7 –Re‐examination of the role of the hydrogen bond in 2‐mercapto substituted derivatives | Zendy

GryffKeller Adam | Zendy; Szczeciński Przemysław | Zendy

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Investigation of the amide rotation in N , N ‐dialkylbenzamides. 7 –Re‐examination of the role of the hydrogen bond in 2‐mercapto substituted derivatives

Author(s) -

GryffKeller Adam,

Szczeciński Przemysław

Publication year - 1985

Publication title -

magnetic resonance in chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0749-1581

DOI - 10.1002/mrc.1260230811

Subject(s) - chemistry , intramolecular force , amide , hydrogen bond , rotation (mathematics) , alkyl , proton nmr , aryl , stereochemistry , internal rotation , medicinal chemistry , carbon 13 nmr , molecule , computational chemistry , organic chemistry , mechanical engineering , geometry , mathematics , engineering

Barriers to the amide rotation in 2‐mercapto‐ N , N ‐dialkylbenzamides [alkyl = CH 3 or CH(CH 3 ) 2 ] and some of their derivatives were measured by dynamic 1 H NMR. For N , N ‐diisopropylamides, barriers to rotation about the carbonyl–aryl bond were also determined. The results show that the intramolecular hydrogen bond has only a very small influence on the measured barriers. In contrast to the literature data, only one set of signals, common to all possible forms of 2‐mercapto‐ N , N ‐dimethylbenzamide, has been observed.

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