NUCLEAR MAGNETIC RESONANCE AND INFRARED STUDIES OF ACYLATED IMIDAZOLIDINONES AND IMIDAZOLIDINETHIONES

Authors
  1. Greenhalgh, R.
  2. Weinberger, M.A.
Corporate Authors
Defence Chemical Biological and Radiation Labs, Ottawa ONT (CAN)
Abstract
The frequency of the ring carbonyl stretching vibration increases with the degree of acylation and the electron-withdrawing power of the acyl group. The methylene protons of the diacylated derivatives show a single peak, the paramagnetic shift of which is similarly dependent on these parameters when the ring current effects are allowed for. This correlation favors the conclusion that the anisotropy of the acyl carbonyl group does not affect the relative methylene proton shift in these compounds and hence they all have the same preferred configuration. In the unsymmetrical 1,3-diacyl compounds the methylene protons are also nearly equivalent. This is explained by mesomeric equalization of the electronic environment of nitrogen atoms 1 and 3. The C=S bond is found to have a strong deshielding influence on all protons.
Report Number
DCBRL-472 — Reprint; Previously accessioned as DSIS 66-02354
Date of publication
01 Jan 1965
Number of Pages
9
Reprinted from
Canadian J of Chemistry, vol 43, 1965, p 3340-3346
DSTKIM No
92-03511
CANDIS No
126880
Format(s):
Hardcopy;Originator's fiche received by DSIS

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