基于氢键和阴离子π相互作用的超环宿主二羧酸盐识别。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-05-06 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.72

Wen-Hui Mi, Teng-Yu Huang, Xu-Dong Wang, Yu-Fei Ao, Qi-Qiang Wang, De-Xian Wang

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引用次数: 0

摘要

二羧酸盐的有效结合是超分子化学中一个重要而又具有挑战性的问题。在这项研究中，我们设计了功能超环作为宿主来容纳大的有机二羧酸阴离子。这些超环是通过从大环前体开始的一锅策略合成的。利用1H NMR滴定研究了宿主与二羧酸盐的结合，发现B4aH对一系列二羧酸盐具有很强的结合亲和性，其结合常数高达6896 M-1。庚二酸（C7 2-）的选择性归因于协同氢键、阴离子-π相互作用和尺寸匹配效应，并得到了DFT优化的支持。

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Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion-π interactions.

The efficient binding of dicarboxylates represents an important yet challenging issue in supramolecular chemistry. In this study, we designed functional ultracycles as hosts to accommodate large organic dicarboxylate anions. These ultracycles were synthesized via a one-pot strategy starting from macrocyclic precursors. Host-dicarboxylate binding was investigated using ¹H NMR titrations, revealing that B4aH exhibits strong binding affinities toward a series of dicarboxylates, with association constants reaching up to 6896 M^-1. The selectivity for heptanedioate (C7 ^2- ) was attributed to cooperative hydrogen bonding, anion-π interactions, and a size-matching effect, as supported by DFT optimizations.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.