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Issue 35, 2013
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Pincher ferrocene-derived cation carboxylate ion pairs in aqueous DMSO

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Abstract

Pincher cationic ferrocene hosts for carboxylate ion guests were synthesized and the binding constants were determined by NMR or UV-Vis titrations. These (di)cationic hosts form tight complexes with benzoate or acetate even in competitive aqueous DMSO solvent. A bis(acylguanidinium) ferrocene dication achieves a remarkable Ka of ∼106 M−1 to acetate in 9 : 1 DMSOH2O and a Ka of 850 M−1 in neat D2O, one of the highest association constants known for a carboxylate complex exploiting only electrostatic interactions in neat water. DFT computations of the binding enthalpy are in good agreement with the experimentally determined association constants. The ferrocene backbone used in these pincher complexes may prove to be a useful semi-flexible scaffold for redox detectable/switchable self-assemblies in aqueous solutions.

Graphical abstract: Pincher ferrocene-derived cation carboxylate ion pairs in aqueous DMSO

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Supplementary files

Article information


Submitted
22 Apr 2013
Accepted
12 Jul 2013
First published
16 Jul 2013

Org. Biomol. Chem., 2013,11, 5827-5835
Article type
Paper

Pincher ferrocene-derived cation carboxylate ion pairs in aqueous DMSO

C. L. Beck, S. A. Berg and A. H. Winter, Org. Biomol. Chem., 2013, 11, 5827 DOI: 10.1039/C3OB40817E

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