1. Quinoline‐Based Silylium Ions: Synthesis, Structure and Lewis Acidity
- Author
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Frédéric Robert, Nivesh Kumar, Claire Laye, Yannick Landais, Institut des Sciences Moléculaires (ISM), and 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)
- Subjects
Silylation ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Quinoline ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,Ion ,chemistry.chemical_compound ,Polymer chemistry ,Lewis acids and bases ,Physical and Theoretical Chemistry - Abstract
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.
- Published
- 2021
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