Quinoline‐Based Silylium Ions: Synthesis, Structure and Lewis Acidity
| Autor: | Frédéric Robert, Nivesh Kumar, Claire Laye, Yannick Landais |
|---|---|
| Přispěvatelé: | Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | European Journal of Organic Chemistry European Journal of Organic Chemistry, Wiley-VCH Verlag, 2021, 2021 (25), pp.3613-3621. ⟨10.1002/ejoc.202100604⟩ |
| ISSN: | 1099-0690 1434-193X |
| DOI: | 10.1002/ejoc.202100604 |
| Popis: | International audience; Heteroarylsilyl cations elaborated from a quinoline skeleton have been prepared from the corresponding silanes and their structures studied by 1 H, 29 Si, and 15 N NMR. DOSY experiments and DFT calculations were also carried out showing that the silyl cation center is stabilized intramolecularly by the quinoline nitrogen atom (N1), forming a highly strained and quasi planar 4-membered ring. Oxygenated and nitrogenated substituents at the C4 position on the quinoline ring were shown to reinforce the Si-N1 interaction through a p- conjugation. The Lewis acidity of this class of silylium was finally determined using Müller's nitrilium method. |
| Databáze: | OpenAIRE |
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