Noncovalent Catch and Release of Carboxylates in Water
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- 作者：Christie L. Beck ; Arthur H. Winter
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：April 4, 2014
- 年：2014
- 卷：79
- 期：7
- 页码：3152-3158
- 全文大小：449K
- 年卷期：v.79,no.7(April 4, 2014)
- ISSN：1520-6904
文摘
Association constants of a bis-(acetylguanidinium)ferrocene dication to various (di)carboxylates were determined through UV鈥搗is titrations. Association constant values greater than 104 M鈥? 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鈥揷arboxylate 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.