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Metal triflates and triflimides as Lewis “superacids”: preparation, synthetic application and affinity tests by mass spectrometry
Author(s) -
Gal JeanFrançois,
Iacobucci Claudio,
Monfardini Ilaria,
Massi Lionel,
Duñach Elisabet,
Olivero Sandra
Publication year - 2013
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3019
Subject(s) - chemistry , lewis acids and bases , mass spectrometry , superacid , triflic acid , catalysis , intramolecular force , ligand (biochemistry) , metal , salt (chemistry) , inorganic chemistry , combinatorial chemistry , organic chemistry , biochemistry , receptor , chromatography
Metal salts of triflic acid, CF 3 SO 2 OH and of triflimidic acid, [CF 3 SO 2 ] 2 NH, often called “Lewis superacids”, are powerful catalysts for several classes of reactions. Typical applications developed at the Institut de Chimie de Nice during the last decade, mostly in the domain of inter‐ and intramolecular carbon–carbon, carbon–oxygen and carbon–sulfur bond formation, are illustrated. During the last three years, the characterization of metal triflates and triflimides by electrospray mass spectrometry was also accomplished in our Institute. Displacement of one anion of the salt by strong neutral ligands was developed as a mean for generating characteristic positive ions. In an effort toward the quantitative description of the ligand/metal bonding and the catalytic role of the Lewis acid, a ligand competition method was devised. An exploratory study attests that subtle structural effects on the donor/acceptor interaction can be evidenced using this simple mass spectrometric method. Copyright © 2012 John Wiley & Sons, Ltd.