Analysis of Hindered Rotation and Magnetic Anisotropy by NMR. Models for Drugs and Agricultural Compounds. The Diels-Alder Adduct of Phencyclone with N-Carbamoylmaleimide

Analysis of NMR spectra of selected model compounds can be of great value in understanding aspects of hindered rotation and magnetic anisotropy in drugs and other compounds of much intrinsic importance. One- and two- dimensional 1 H NMR (300 MHz) and 13 C NMR (75 MHz) studies have been performed at...

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Bibliographic Details
Published in:Spectroscopy letters 1997-06, Vol.30 (4), p.727-749
Main Authors: Bynurn, Kevin, Rothchild, Robert
Format: Article
Language:English
Subjects:
Analysis
Anisotropy
C NMR
COSY
DEPT
Dynamic NMR
H NMR
One- and two-dimensional NMR
Pharmaceuticals
Restricted rotation
Stereochemistry
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Summary:Analysis of NMR spectra of selected model compounds can be of great value in understanding aspects of hindered rotation and magnetic anisotropy in drugs and other compounds of much intrinsic importance. One- and two- dimensional 1 H NMR (300 MHz) and 13 C NMR (75 MHz) studies have been performed at ambient temperatures on the Diels-Alder adduct of N-carbamoylmaleimide with phencyclone, 1. The data for the adduct, 2 , are interpreted as being consistent with: a) essentially slow exchange limit (SEL) spectra with respect to rotation about the C(sp 2 )-C(sp 3 ) bonds to the unsubstituted bridgehead phenyls, b) slow rotation on the NMR timescale for the amide NH 2 group, and c) fast rotation about the amide N-CONH 2 bond to the ring nitrogen. The assigned endo stereochemistry for adduct 2 and the conclusions regarding bond rotation rates are based on numbers of observed NMR signals and magnetic anisotropic effects. Full 1 H NMR spectral assignments and preliminary 13 C assignments are presented.
ISSN:0038-7010
1532-2289
DOI:10.1080/00387019708006695