title: Combining proton and electron transfer to modulate the stability of cucurbit[7]uril complexes.
abstract: (Ferrocenylmethyl)methylammonium (1H(+)) is an excellent cationic guest for inclusion complexation by the cucurbit[7]uril host. However, deprotonation of the guest leads to a decrease of 14.8 kJ mol(-1) in the overall stability of its inclusion complex, and one-electron oxidation of the guest's ferrocene residue further diminishes the complex stability by another 12.3 kJ mol(-1). Overall, guest deprotonation followed by its oxidation constitutes an accessible method to lower the equilibrium association constant for the CB7·1H(+) complex by more than 4 orders of magnitude.
authors.affiliation: Center for Supramolecular Science and Department of Chemistry, University of Miami, Coral Gables, Florida 33124-0431, United States.
authors.forename: Wei
authors.initials: W
authors.lastname: Li
authors.forename: Angel E
authors.initials: AE
authors.lastname: Kaifer
mesh_terms: D001952:Bridged-Ring Compounds / Q000737:chemistry*; D004583:Electrons; D006863:Hydrogen-Ion Concentration; D007093:Imidazoles / Q000737:chemistry*; D011522:Protons; D013816:Thermodynamics; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
chemical_list: D001952:Bridged-Ring Compounds; D007093:Imidazoles; D011522:Protons; C456276:cucurbit(7)uril; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils