Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF) and Catastrophe Theory Analysis of the Umpolung Reaction
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 ben...
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| Language: | English |
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MDPI AG
2025-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/2/378 |
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| author | Michal Michalski Slawomir Berski |
| author_facet | Michal Michalski Slawomir Berski |
| author_sort | Michal Michalski |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-d09d24d1ced94fbebeb312cce0eac7a3 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-d09d24d1ced94fbebeb312cce0eac7a32025-01-24T13:43:50ZengMDPI AGMolecules1420-30492025-01-0130237810.3390/molecules30020378Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF) and Catastrophe Theory Analysis of the Umpolung ReactionMichal Michalski0Slawomir Berski1Centre of New Technologies, University of Warsaw, 02-097 Warsaw, PolandFaculty of Chemistry, University of Wroclaw, 50-383 Wroclaw, PolandThis 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.https://www.mdpi.com/1420-3049/30/2/378umpolung reactionbenzoin condensationBETELF |
| spellingShingle | Michal Michalski Slawomir Berski Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF) and Catastrophe Theory Analysis of the Umpolung Reaction Molecules umpolung reaction benzoin condensation BET ELF |
| title | Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF) and Catastrophe Theory Analysis of the Umpolung Reaction |
| title_full | Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF) and Catastrophe Theory Analysis of the Umpolung Reaction |
| title_fullStr | Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF) and Catastrophe Theory Analysis of the Umpolung Reaction |
| title_full_unstemmed | Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF) and Catastrophe Theory Analysis of the Umpolung Reaction |
| title_short | Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF) and Catastrophe Theory Analysis of the Umpolung Reaction |
| title_sort | mechanistic pathways in cyanide mediated benzoin condensation a comprehensive electron localisation function elf and catastrophe theory analysis of the umpolung reaction |
| topic | umpolung reaction benzoin condensation BET ELF |
| url | https://www.mdpi.com/1420-3049/30/2/378 |
| work_keys_str_mv | AT michalmichalski mechanisticpathwaysincyanidemediatedbenzoincondensationacomprehensiveelectronlocalisationfunctionelfandcatastrophetheoryanalysisoftheumpolungreaction AT slawomirberski mechanisticpathwaysincyanidemediatedbenzoincondensationacomprehensiveelectronlocalisationfunctionelfandcatastrophetheoryanalysisoftheumpolungreaction |