AI Article Synopsis
- The study investigates how different upper-rim-substituted C(2)-resorcinarenes interact with tetramethylammonium salts in both gas phase and solution using advanced techniques.
- The binding strengths observed in the gas phase are influenced by the electronic properties of the substituents, while in solution, halogenated resorcinarenes show unexpectedly high binding due to interactions with counter anions.
- This research underscores the significance of weak interactions in chemical recognition and emphasizes the value of comparing gas-phase and solution data for a deeper understanding.
Article Abstract
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.
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| http://dx.doi.org/10.1002/chem.201103991 | DOI Listing |
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