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Recognition of Ionic Guests by Ionic β‐Cyclodextrin Derivatives
Author(s) -
Wenz Gerhard,
Strassnig Christian,
Thiele Carolin,
Engelke Annegret,
Morgenstern Bernd,
Hegetschweiler Kaspar
Publication year - 2008
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.200800295
Subject(s) - isothermal titration calorimetry , chemistry , ionic bonding , cationic polymerization , protonation , stoichiometry , cyclodextrin , computational chemistry , ion , crystallography , organic chemistry
Inclusion compounds of cationic, anionic, and neutral p ‐substituted derivatives of tert‐ butylbenzene complexed in β‐cyclodextrin and its ionic 6‐mono and 6‐hepta derivatives were systematically investigated by isothermal titration calorimetry (ITC). All inclusion compounds showed 1:1 stoichiometry with binding constants ranging from 10 to 3×10 6 M −1 . The binding free energies could be subdivided into apolar and electrostatic contributions. The electrostatic interactions could be quantitatively described by Coulomb's law by taking into account the degree of protonation of hosts and guests, the orientations of the guests within the hosts, and ion shielding as described by the Debye–Hückel–Onsager theory. The orientations of the guests within the cyclodextrin cavities were determined by ROESY NMR spectroscopy.