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1 H NMR utilization of through‐space effects: III —configuration of oximes and analogous compounds
Author(s) -
Rouillard M.,
Girault Y.,
Decouzon M.,
Azzaro M.
Publication year - 1983
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/omr.1270210604
Subject(s) - oxime , dihedral angle , chemistry , chemical shift , electric field , hydrochloride , nitrogen , proton , crystallography , space (punctuation) , iodide , computational chemistry , stereochemistry , medicinal chemistry , molecule , physics , organic chemistry , hydrogen bond , quantum mechanics , linguistics , philosophy
The configurational assignment of Z and E nitrogen derivatives () of 3,5,5‐trimethyl‐2‐cyclohexen‐1‐one was made taking into consideration the through‐space effects on oxime, O ‐methyloxime, dimethylhydrazone, tert ‐butylimine, N , N , N ‐trimethylhydrazonium iodide and oxime hydrochloride derivatives. The relationship between the magnitude of the chemical shifts of the α‐protons and the dihedral angle formed by the α‐CH bond and the CNOH plane was interpreted in terms of the geometrical dependence of the electric field effect. For the different Y substituents, the change in chemical shift between the Z and the E configuration of the proton near the functional group was mainly dependent on the electric field effect.