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- Title
An Experimental Acidity Scale for Intramolecularly Stabilized Silyl Lewis Acids.
- Authors
Künzler, Sandra; Rathjen, Saskia; Merk, Anastasia; Schmidtmann, Marc; Müller, Thomas
- Abstract
A new NMR‐based Lewis acidity scale is suggested and its application is demonstrated for a family of silyl Lewis acids. The reaction of p‐fluorobenzonitrile (FBN) with silyl cations that are internally stabilized by interaction with a remote chalcogenyl or halogen donor yields silylated nitrilium ions with the silicon atom in a trigonal bipyramidal coordination environment. The 19F NMR chemical shifts and the 1J(CF) coupling constants of these nitrilium ions vary in a predictable manner with the donor capability of the stabilizing group. The spectroscopic parameters are suitable probes for scaling the acidity of Lewis acids. These new probes allow for the discrimination between very similar Lewis acids, which is not possible with conventional NMR tests, such as the well‐established Gutmann–Beckett method.
- Subjects
LEWIS acids; ACIDITY; COUPLING constants; NUCLEAR magnetic resonance spectroscopy; LEWIS acidity
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 66, p15123
- ISSN
0947-6539
- Publication type
Academic Journal
- DOI
10.1002/chem.201903241