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Ion‐Pair Recognition of Tetramethylammonium Salts by Halogenated Resorcinarenes
Author(s) -
Beyeh N. Kodiah,
Weimann Dominik P.,
Kaufmann Lena,
Schalley Christoph A.,
Rissanen Kari
Publication year - 2012
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.201103991
Subject(s) - tetramethylammonium , chemistry , resorcinarene , fourier transform ion cyclotron resonance , electrospray ionization , hydrogen bond , mass spectrometry , tetramethylammonium hydroxide , ion , phase (matter) , inorganic chemistry , gas phase , titration , ion cyclotron resonance , computational chemistry , organic chemistry , molecule , chromatography , cyclotron
The non‐covalent interactions of different upper‐rim‐substituted C 2 ‐resorcinarenes with tetramethylammonium salts were analyzed in the gas phase in an Electrospray Ionization Fourier‐transform ion‐cyclotron‐resonance (ESI‐FTICR) mass spectrometer and by 1 H NMR titrations. The order of binding strengths of the hosts towards the tetramethylammonium cation in the gas phase reflects the electronic nature of the substituents on the upper rim of the resorcinarene. In solution, however, a different trend with particularly high binding constants for halogenated resorcinarenes has been observed. This trend can be explained by a synergetic effect originating from the interaction of the halogenated resorcinarenes with the counter anions through hydrogen bonding. This study highlights the importance of weak interactions in recognition processes and points out the benefits of comparing the gas‐phase data with results obtained from solution experiments.