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Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF)
Michal Michalski1, Slawomir Berski2
1Centre of New Technologies, University of Warsaw, 02-097 Warsaw, Poland.
Abstract:
This research investigates the mechanism of the cyanide-type umpolung reaction in benzoin condensation using topological analysis of ELF and catastrophe theory. The study achieves a comprehensive understanding of the evolution of chemical bonds and non-bonding electron density in the reaction of benzaldehyde and cyanide ions. The results reveal that the reaction proceeds through five transition state structures, with the formation of Lapworth's cyanohydrin being the rate-determining step. The study characterises topological catastrophes in the evolution of the ELF field and provides a detailed description of the evolution of electron density in the mechanism of the reaction. An in-depth analysis of ELF catastrophes confirms the well-established Lapworth mechanism.
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