Anion receptors containing NH binding sites: Hydrogen-bond formation or neat proton transfer?

被引：111

作者：

Amendola, V

Boiocchi, M

Fabbrizzi, L

Palchetti, A

机构：

[1] Univ Pavia, Dipartimento Chim Gen, I-27100 Pavia, Italy

[2] Univ Pavia, Ctr Grandi Strumenti, I-27100 Pavia, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2005年 / 11卷 / 01期

关键词：

anions; hydrogen bonds; molecular recognition; proton transfer; receptors;

D O I：

10.1002/chem.200400592

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

When the amide-containing receptor I+ is in a solution of dimethyl sulfoxide (DMSO) in the presence of basic anions (CH3COO-, F-, H2PO4-), it undergoes deprotonation of the -NH fragment to give the corresponding zwitterion, which can be isolated as a crystalline solid. In the presence of less basic anions (Cl-, Br-, NO3-), 1(+) establishes true hydrogen-bond interactions of decreasing intensity. The less acidic receptor 2(+) undergoes neat proton transfer with only the more basic anions CH3COO- and F-, and establishes hydrogen-bond interactions with H2PO4-. An empirical criterion for discerning neutralisation and hydrogen bonding, based on UV/Vis and H-1 NMR spectra, is proposed.

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页码：120 / 127

页数：8

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