Premium
Monitoring Fluoride Binding in DMSO: Why is a Singular Binding Behavior Observed?
Author(s) -
Goursaud Matthieu,
De Bernardin Paolo,
Dalla Cort Antonella,
Bartik Kristin,
Bruylants Gilles
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200165
Subject(s) - fluoride , chemistry , titration , nuclear magnetic resonance spectroscopy , inorganic chemistry , spectroscopy , selectivity , molecular recognition , combinatorial chemistry , molecule , organic chemistry , catalysis , physics , quantum mechanics
Fluoride recognition by molecular receptors is attracting much interest in the scientific community and a variety of approaches are used to achieve recognition with high affinity and selectivity. Most of the synthetic systems reported have been extensively studied in organic solvents by using tetrabutylammonium fluoride (TBAF) as the source of fluoride. In many cases, titration behaviors are observed that cannot be ascribed to a classical 1:1 binding isotherm. By using UV/Vis, 19 F NMR, and 1 H NMR spectroscopy we have been able to highlight that the equilibrium between the fluoride and the corresponding bihalide ion, HF 2– , which is inevitably generated in situ due to trace amounts of water, can be at the origin of this singular behavior. Our results highlight that when undertaking titrations with fluoride in DMSO, the data can be affected by the fluoride–bihalide equilibrium and that the latter species can even be the dominating species at low TBAF concentrations.