Related Experiment Video
Updated: Apr 7, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
Published on: August 18, 2017
Chiral Memory in Silylium Ions
P Ducos1, V Liautard1, F Robert2
1Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux 351, Cours de la libération 33405 Talence cedex (France).
Abstract:
The configurational stability of the chiral silicon center in Lewis base-stabilized silyliums has been studied. Complete retention of configuration at silicon is observed at low temperature in silylium ions stabilized by lone-pair interactions. In contrast, loss of chiral memory is observed with systems involving π-interactions. Epimerization of the silicon center was observed by simply allowing equilibration of the diastereomeric silyliums at RT or by adding a catalytic amount of a chelating solvent. Conditions for the transfer of axial chirality to Si-centered chirality were shown to rely on the strength of the Lewis base-silylium ion interaction.
Related Concept Videos
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Chirality
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Molecules with Multiple Chiral Centers
Prochirality
Chirality in Nature
Naming Enantiomers

