Binding Interactions between a Ferrocenylguanidinium Guest and Cucurbit[n]uril Hosts
| Autor: | Sonia Bruña, Angel E. Kaifer, Isabel Cuadrado, Mehdi Rashvand Avei, Vivian Iglesias |
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| Rok vydání: | 2016 |
| Předmět: |
Electrospray
Aqueous solution 010405 organic chemistry Stereochemistry Electrospray ionization Organic Chemistry 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Crystallography chemistry Proton NMR Moiety Equilibrium constant Derivative (chemistry) Stoichiometry |
| Zdroj: | The Journal of organic chemistry. 82(1) |
| ISSN: | 1520-6904 |
| Popis: | The binding interactions between a novel ferrocenylguanidinium derivative (FcG+) and the macrocyclic hosts cucurbit[7]uril (CB7) and cucurbit[8]uril (CB8) were investigated in aqueous solution. 1H NMR spectroscopic experiments indicated that both hosts form stable 1:1 inclusion complexes with FcG+, in which the ferrocenyl group is engulfed by the host cavity. The stoichiometry of the CB7·FcG+ complex was also confirmed by electrospray mass spectrometric (ESI MS) experiments. The association equilibrium constants (K) were determined from NMR competition experiments. The measured K values were 3.5 × 109 and 2.5 × 108 M–1 for CB7 and CB8, respectively, in 50 mM sodium acetate-d3 D2O solution (pD 4.7). DFT computational studies confirmed the 1:1 stoichiometry and the inclusion character of both complexes. Voltammetric experiments were carried out to measure the complexation-induced shifts on the half-wave potentials for the one-electron oxidation of the ferrocenyl moiety. Complexation by CB7 led to a 12 mV an... |
| Databáze: | OpenAIRE |
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