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The First Organosilver(III) Fluoride, [PPh 4 ][(CF 3 ) 3 AgF]
Author(s) -
JovenSancho Daniel,
Baya Miguel,
Martín Antonio,
Orduna Jesús,
Menjón Babil
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905771
Subject(s) - chemistry , fluoride , dissociation (chemistry) , trifluoromethyl , yield (engineering) , nucleophile , collision induced dissociation , hydrolysis , medicinal chemistry , ligand (biochemistry) , mass spectrometry , crystallography , inorganic chemistry , tandem mass spectrometry , organic chemistry , catalysis , physics , thermodynamics , alkyl , receptor , chromatography , biochemistry
Abstract Organosilver(III) fluoride complexes have been assigned a key role in different fluorination processes. To the best of our knowledge, however, none of them seem to have been isolated or even detected thus far. Here we report on the successful synthesis of the trifluoromethyl derivative [PPh 4 ][(CF 3 ) 3 AgF], which has been isolated in high yield. The thermodynamic stability of the Ag−F bond is shown by calculation and demonstrated by multistage mass spectrometry (MS n ) under collision‐induced dissociation (CID) conditions. Nevertheless, the substantial elongation found in the Ag−F bond (X‐ray) is correlated with a marked nucleophilic character of the terminal F ligand. This Ag−F bond is, in fact, quite reactive: it suffers hydrolysis and is also solvolyzed by thiols.