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Issue 36, 2014
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Computational and ion mobility MS study of (all-S)-cyclohexylhemicucurbit[6]uril structure and complexes

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Abstract

A computational study of (all-S)-cyclohexylhemicucurbit[6]uril and its complexes with anions (Cl, Br, I and HCOO), the proton (H+) and non-dissociated acid (HCl, HBr, HI and HCOOH) guests was performed. The geometries of guest–host complexes were optimized via density functional theory using the BP86 functional, SV(P) basis set and Stuttgart pseudopotentials for iodide. Binding affinities and their trends were evaluated at the BP86/TZVPD level of theory. In addition, the quantum theory of atoms in molecules was used to gain insight into guest–host interactions. A computational study in the gas phase and ion-mobility mass-spectrometry analysis revealed that the studied macrocycle formed inclusion complexes with anions. Protonation of the macrocycle is preferred at the nitrogen atom pointing inside of the cavity. In the studied conditions, non-dissociated acids formed complexes at the oxygen atom pointing outside of the macrocycle.

Graphical abstract: Computational and ion mobility MS study of (all-S)-cyclohexylhemicucurbit[6]uril structure and complexes

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Publication details

The article was received on 20 May 2014, accepted on 08 Jul 2014 and first published on 11 Jul 2014


Article type: Paper
DOI: 10.1039/C4CP02202E
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Citation: Phys. Chem. Chem. Phys., 2014,16, 19198-19205
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    Computational and ion mobility MS study of (all-S)-cyclohexylhemicucurbit[6]uril structure and complexes

    M. Öeren, E. Shmatova, T. Tamm and R. Aav, Phys. Chem. Chem. Phys., 2014, 16, 19198
    DOI: 10.1039/C4CP02202E

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