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14 N NMR studies on some N ‐sulphinylamines
Author(s) -
Sicińska W.,
Stefaniak L.,
Witanowski M.,
Webb G. A.
Publication year - 1981
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.1270150306
Subject(s) - cndo/2 , alkyl , aryl , nitrogen , chemistry , molecule , crystallography , stereochemistry , medicinal chemistry , organic chemistry
High precision 14 N nuclear screening data are presented for some alkyl‐ and aryl‐ N ‐sulphinylamines. For the alkyl compounds the β effect is seen to produce a decrease in screening and the opposite influence from the γ effect is also observed. An exception to the general tendency for the β effect is noted for (CH 3 ) 3 CNSO. CNDO/S parameterized nitrogen screening calculations show that for this molecule the distorted cis form, with all of the methyl carbons rotated out of the CNSO plane, is the most probable structure. A similar effect is observed upon substituting the bulky tert ‐butyl group in the 2 position of the aryl compounds studied. Nitrogen screening calculations again indicate the presence of the distorted cis form.