Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

2014

Journal or Book Title

The Journal of Organic Chemistry

Volume

79

Issue

7

First Page

3152

Last Page

3158

DOI

10.1021/jo500276h

Abstract

Association constants of a bis-(acetylguanidinium)ferrocene dication to various (di)carboxylates were determined through UV–vis titrations. Association constant values greater than 104 M–1 were determined for both phthalate and maleate carboxylates to the bis-(acetylguanidinium)ferrocene salt in pure water. Density functional theory computations of the binding enthalpy of the rigid carboxylates for these complexes agree well with the experimentally determined association constants. Catch and release competitive binding experiments were done by NMR for the cation–carboxylate ion-pair complexes with cucurbit[7]uril, and they show dissociation of the ion-pair complex upon addition of cucurbit[7]uril and release of the free (di)carboxylate.

Comments

Reprinted (adapted) with permission from J. Org. Chem., 2014, 79 (7), pp 3152–3158. Copyright 2014 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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