6533b823fe1ef96bd127e243
RESEARCH PRODUCT
Ion-Pair Recognition of Tetramethylammonium Salts by Halogenated Resorcinarenes
Lena KaufmannDominik P. WeimannN. Kodiah BeyehKari RissanenChristoph A. Schalleysubject
Models MolecularSpectrometry Mass Electrospray IonizationMagnetic Resonance SpectroscopyHalogenationPhenylalanineElectrospray ionizationInorganic chemistryMass spectrometryCatalysischemistry.chemical_compoundComputational chemistryCalixareneta116IonsTetramethylammoniumHydrogen bondOrganic ChemistryHydrogen BondingGeneral ChemistryNuclear magnetic resonance spectroscopyResorcinareneQuaternary Ammonium CompoundschemistryProton NMRSaltsCalixarenesdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-12-20 | Chemistry - A European Journal |