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Mechanistic insights into the (3 + 2) cycloaddition of azomethine ylide with dimethyl acetylenedicarboxylate <i>via</i> bond evolution theory

Mohamed Chellegui, Raghad Mowafak Al-Mokhtar, Raad Nasrullah Salih, Lakhdar Benhamed, Sofiane Benmetir, Jesus Vicente de Julián‐Ortiz, Haydar Mohammad‐Salim, Ali Ben Ahmed

2025RSC Advances10 citationsDOIOpen Access PDF

Abstract

pathway exhibiting a higher degree of asynchronicity. Global Electron Density Transfer (GEDT) values confirmed the moderately to distinctly polar nature of the pathways. Finally, detailed Electronic Localization Function (ELF) topological analysis and Bonding Evolution Theory (BET) elucidated the asynchronous, multistage mechanism involving six structural stability domains (SSDs), characterizing the formation of new bonds through a sequence of topological catastrophes. Non-Covalent Interaction (NCI) analysis provided visual and quantitative evidence of attractive and repulsive intermolecular forces influencing the TS geometries.

Topics & Concepts

Dimethyl acetylenedicarboxylateAzomethine ylideCycloadditionYlideChemistryPolarMedicinal chemistryStereochemistryComputational chemistryOrganic chemistryPhysicsCatalysis1,3-Dipolar cycloadditionAstronomyOrganic Chemistry Cycloaddition ReactionsSynthesis and Catalytic ReactionsSynthesis and Characterization of Pyrroles
Mechanistic insights into the (3 + 2) cycloaddition of azomethine ylide with dimethyl acetylenedicarboxylate <i>via</i> bond evolution theory | Litcius