Evidences of the Stabilization for Weeks of the Benzyl Cation in Zeolites
[EN] The benzyl cation is an iconic intermediate in organic chemistrywhich has not been isolated yet. Here, we show that the incorpo-ration of tropylium cations in commercially available sodium zeo-lites, after cation exchange, plausibly triggers the spontaneousformation of benzyl cations inside the...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2025 |
| País: | España |
| Institución: | Universitat Politècnica de València (UPV) |
| Repositorio: | RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia |
| Idioma: | inglés |
| OAI Identifier: | oai:dnet:riunet______::9f16ff0a9aa8217f44720685b11adc7a |
| Acceso en línea: | https://riunet.upv.es/handle/10251/233437 |
| Access Level: | acceso abierto |
| Palabra clave: | Benzyl Cation Zeolites Organic chemistry |
| Sumario: | [EN] The benzyl cation is an iconic intermediate in organic chemistrywhich has not been isolated yet. Here, we show that the incorpo-ration of tropylium cations in commercially available sodium zeo-lites, after cation exchange, plausibly triggers the spontaneousformation of benzyl cations inside the zeolite pores at room tem-perature. The zeolite plays a bifunctional role as a host. First, theunimolecular rearrangement reaction occurs by the ability of thezeolite to isolate tropylium molecules and achieve the requiredenergy to transform tropylium into benzyl cations. Then, the com-partmentalized nature of the zeolite framework avoids the quench-ing of the so¿formed benzyl cations with each other, or any othernucleophile, allowing lifetimes of weeks for the benzyl cationsunder ambient conditions. In this way, a customary organic char-acterization of the zeolite¿embedded benzyl cation by absorptionultraviolet¿visible spectrophotometry and 13C nuclear magneticresonance (13C NMR) has now been possible. Transient absorptionspectroscopy and reactivity studies, together with moleculardynamic calculations, further support the formation of the benzylcation inside the zeolite. These results bring this fundamental car-bocation intermediate to our laboratories as a manageable organiccompound. |
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