ArticleMolecules (Basel, Switzerland)2023
On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions between Aryl Azides and Ethyl Propiolate.
Article in Molecules (Basel, Switzerland), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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11 citing papers in PubMed.
- On the Question of the Regio-, Stereoselectivity and the Molecular Mechanism of the (3+2) Cycloaddition Reaction Between (Molecules (Basel, Switzerland) · 2025Article
- On the Question of the Regio-Orientation, Stereo-Orientation and Molecular Mechanism in the Cascade Cycloaddition/Rearrangement/Elimination Processes Leading to Nitro-Substituted Thiopyran Analogs: DFT Computational Study.International journal of molecular sciences · 2025Article
- On the Question of the Course of the Hetero Diels-Alder Reactions BetweenMolecules (Basel, Switzerland) · 2025Article
- The Puzzle of the New Type of Intermediate in the Course of [2 + 2] Cycloaddition with the Participation of Conjugated Nitroalkenes: MEDT Computational Study.Molecules (Basel, Switzerland) · 2025Article
- The Puzzle of the Regioselectivity and Molecular Mechanism of the (3+2) Cycloaddition Reaction Between E-2-(Trimethylsilyl)-1-Nitroethene and ArylonitrileMolecules (Basel, Switzerland) · 2025Article
- Unexpected Course of Reaction Between (1Molecules (Basel, Switzerland) · 2024Article
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- A New Insight into the Molecular Mechanism of the Reaction between 2-Methoxyfuran and Ethyl (Molecules (Basel, Switzerland) · 2024Article
- Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study.Molecules (Basel, Switzerland) · 2024Article
- A DFT Study on the Molecular Mechanism of Additions of Electrophilic and Nucleophilic Carbenes to Non-Enolizable Cycloaliphatic Thioketones.Molecules (Basel, Switzerland) · 2021Article
- The Azide-Allene Dipolar Cycloaddition: Is DFT Able to Predict Site- and Regio-Selectivity?Molecules (Basel, Switzerland) · 2021Article
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Abstract
The molecular mechanism of the [3+2] cycloaddition reactions between aryl azides and ethyl propiolate was evaluated in the framework of the Molecular Electron Density Theory. It was found that independently of the nature of the substituent within the azide molecule, the cycloaddition process is realized via a polar but single-step mechanism. All attempts of localization as postulated earlier by Abu-Orabi and coworkers' zwitterionic intermediates were not successful. At the same time, the formation of zwitterions with an "extended" conformation is possible on parallel reaction paths. The ELF analysis shows that the studied cycloaddition reaction leading to the 1,4-triazole proceeds by a two-stage one-step mechanism. It also revealed that both zwitterions are created by the donation of the nitrogen atom's nonbonding electron densities to carbon atoms of ethyl propiolate.
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