Quaternary Ammonium Salts Interact with Enolates and Sulfonates via Formation of Multiple +N-C-H Hydrogen Bonding Interactions

Autor: Grazia Bencivenni, Nathalie Saraiva Rosa, Paolo Grieco, Malachi W. Gillick-Healy, Brian G. Kelly, Brendan Twamley, Mauro F. A. Adamo
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: Catalysts, Vol 12, Iss 7, p 803 (2022)
Druh dokumentu: article
ISSN: 2073-4344
DOI: 10.3390/catal12070803
Popis: We report herein sharp physical evidence, i.e., single-crystal X-ray diffraction and 1H-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 1H-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.
Databáze: Directory of Open Access Journals
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