A comparative study of dynamic NMR spectroscopy in analysis of selected N-alkyl-, N-acyl-, and halogenated cytisine derivatives

New halogenated derivatives of (-)-cytisine were synthesized: 3-bromo- N-acetylcytisine, 5-bromo- N-acetylcytisine, 3,5-dibromo- N-acetylcytisine, 3-iodo- N-acetylcytisine, 5-iodo- N-acetylcytisine, 3,5-diiodo- N-acetylcytisine. Their structures were established on the basis of their NMR spectra and...

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Bibliographic Details
Published in:Journal of molecular structure 2011-01, Vol.985 (2), p.157-166
Main Authors: Przybył, Anna K., Kubicki, Maciej
Format: Article
Language:English
Subjects:
Boats
Conformational equilibrium
Cytisine
Dynamic NMR spectroscopy
N-cytisine derivatives
X-ray of cytisine derivatives
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Summary:New halogenated derivatives of (-)-cytisine were synthesized: 3-bromo- N-acetylcytisine, 5-bromo- N-acetylcytisine, 3,5-dibromo- N-acetylcytisine, 3-iodo- N-acetylcytisine, 5-iodo- N-acetylcytisine, 3,5-diiodo- N-acetylcytisine. Their structures were established on the basis of their NMR spectra and X-ray diffraction method. The crystal structures confirmed the chair conformation of ring C, while in solution all these compounds are in cis–trans conformational equilibrium with ring C in chair and boat conformation. Additionally, the correct X-ray structure of N-benzylcytisine was resolved.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2010.10.036