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Spectroscopic studies on N , N ‐dimethylamides—I: Structure‐reactivity correlation for rotational barriers from a nuclear magnetic resonance study of p ‐ and m ‐substituted N , N ‐dimethylbenzamides
Author(s) -
Korver P. K.,
Spaargaren K.,
van der Haak P. J.,
de Boer Th. J.
Publication year - 1970
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270020309
Subject(s) - substituent , reactivity (psychology) , chemistry , amide , resonance (particle physics) , nuclear magnetic resonance , ring (chemistry) , crystallography , solvent , rotational correlation time , stereochemistry , molecule , atomic physics , organic chemistry , physics , medicine , alternative medicine , pathology
Abstract Rotational barriers in 21 p ‐ and m ‐substituted N , N ‐dimethylbenzamides in CDCl 3 as solvent have been determined using the intensity ratio method of Woodbrey. These data compare very well with values from the literature 1 obtained with a total line shape analysis. From structure‐reactivity correlations evidence has been obtained for a relatively strong resonance interaction between the substituent in the aromatic ring and the partially double amide bond.