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Título: | A molecular electron density theory study of the [3 + 2] cycloaddition reaction of nitrones with ketenes |
Autor: | Ríos-Gutiérrez, Mar; Darù, Andrea CSIC ORCID; Tejero, Tomás CSIC ORCID; Domingo, Luis R.; Merino, Pedro CSIC ORCID | Fecha de publicación: | 2017 | Editor: | Royal Society of Chemistry (UK) | Citación: | Organic and Biomolecular Chemistry 15(7): 1618-1627 (2017) | Resumen: | The [3 + 2] cycloaddition (32CA) reaction between nitrones and ketenes has been studied within the Molecular Electron Density Theory (MEDT) at the Density Functional Theory (DFT) MPWB1K/6-311G(d,p) computational level. Analysis of the conceptual DFT reactivity indices allows the explanation of the reactivity, and the chemo- and regioselectivity experimentally observed. The particular mechanism of this 32CA reaction involving low electrophilic ketenes has been elucidated by using a bonding evolution theory (BET) study. It is determined that this reaction takes place in one kinetic step only but in a non-concerted manner since two stages are clearly identified. Indeed, the formation of the second C-O bond begins when the first O-C bond is already formed. This study has also been applied to predict the reactivity of nitrones with highly electrophilic ketenes. Interestingly, this study predicts a switch to a two-step mechanism due to the higher polar character of this zw-type 32CA reaction. In both cases, BET supports the non-concerted nature of the 32CA reactions between nitrones and ketenes. | Versión del editor: | https://doi.org/10.1039/C6OB02768G | URI: | http://hdl.handle.net/10261/155785 | DOI: | 10.1039/C6OB02768G | Identificadores: | doi: 10.1039/C6OB02768G issn: 1477-0520 e-issn: 1477-0539 |
Aparece en las colecciones: | (ISQCH) Artículos |
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ketenes.pdf | 1,28 MB | Adobe PDF | Visualizar/Abrir |
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