6533b7d8fe1ef96bd126afa7
RESEARCH PRODUCT
Alkali metal mediated resorcarene capsules: An ESI-FTICRMS study on gas-phase structure and cation binding of tetraethyl resorcarene and its per-methylated derivative
Pirjo VainiotaloMarko MäkinenKari Rissanensubject
Models MolecularSpectrometry Mass Electrospray IonizationCation bindingFourier AnalysisHydrogen bondChemistryStereochemistryElectrospray ionizationMolecular ConformationHydrogen BondingAlkaliesIon cyclotron resonance spectrometryMethylationFourier transform ion cyclotron resonanceMolecular recognitionMetalsStructural BiologyIntramolecular forcePolymer chemistryMoleculePolycyclic CompoundsSpectroscopydescription
AbstractElectrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI-FTICRMS) with additional ab initio calculations were used to examine the alkali metal cation binding selectivity (i.e., molecular recognition) and host properties of tetraethyl resorcarene (1) and its per-methylated derivative (2). The significance of intramolecular hydrogen bonding for the crown conformation was demonstrated. The presence of intramolecular flip-flop hydrogen bonding in 1 was confirmed both with calculations and in ND3-exchange experiments. All the alkali metal cations formed host–guest complexes by docking inside the cavity of the host. Complexation with the larger cations, especially Cs+, was favored. All the alkali metal cations also formed dimeric resorcarene capsules with 1. The capsules were directly H-bonded species, with no linking solvent molecules. ND3-exchange experiments and molecular modeling revealed the significance of direct intermolecular H-bonding for the crown conformation of 1 and stability of the capsule structure.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-08-01 | Journal of the American Society for Mass Spectrometry |