Journal
CATALYSTS
Volume 12, Issue 7, Pages -Publisher
MDPI
DOI: 10.3390/catal12070803
Keywords
quaternary ammonium salts; phase-transfer catalysis; unusual H-bond
Categories
Funding
- Irish Research Council (IRC) grant [EPSPG/2017/347]
- H2020-MSCA-RISE QuatSalts Grant [690882]
- H2020-MSCA-RISE GreenX4Drug Grant [823939]
- Irish Research Council (IRC) [EPSPG/2017/347] Funding Source: Irish Research Council (IRC)
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This study provides physical evidence confirming that quaternary ammonium species interact with anions through a set of directional ion-dipole cooperative hydrogen bonding interactions. This finding is important for the rational design of catalysts and understanding these species in asymmetric catalysis.
We report herein sharp physical evidence, i.e., single-crystal X-ray diffraction and H-1-NMR spectral data, confirming that quaternary ammonium species interact with anions via a set of directional ion-dipole cooperative N+-C-H unusual H-bonding interactions and not via pure non-directional ionic electrostatic interactions. This finding, which has been often invoked by calculations, is herein substantiated by the preparation of two model compounds and an analysis of their X-ray crystal structures in the solid state and H-1-NMR spectra in solution. These observations are particularly pertinent for the rational design of novel catalyses and catalysts and providing guidance to an understanding of these species in solution and during asymmetric enantioselective catalysis.
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