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Aromatic imine stereochemistry as studied by 13 C and 1 H NMR of 15 N‐enriched materials
Author(s) -
Buchanan Gerald W.,
Dawson Brian A.
Publication year - 1980
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.1270130416
Subject(s) - steric effects , chemistry , imine , aryl , chemical shift , carbon 13 nmr , resonance (particle physics) , stereochemistry , crystallography , nuclear magnetic resonance spectroscopy , nmr spectra database , spectral line , organic chemistry , physics , alkyl , catalysis , particle physics , astronomy
A series of thirteen 15 N‐enriched N ‐aryl imines derived from benzaldehydes and acetophenones have been prepared and examined by 13 C and 1 H NMR. Preferred conformations of the C‐arvl and N ‐aryl rings have been deduced from 13 C chemical shifts and 13 C‐ 15 N couplings. Evidence for steric inhibition of resonance in O ‐alkylated materials is presented. Relative signs of 1 J (CN) and 2 J (CCN) have been determined in some compounds. An E: Z interconversion barrier of 21.6 kcal mol −1 has been obtained from 1 H NMR coalescence data.