Quantifying the ability of the CF2H group as a hydrogen bond donor.

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-20 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.11
Matthew E Paolella, Daniel S Honeycutt, Bradley M Lipka, Jacob M Goldberg, Fang Wang
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引用次数: 0

Abstract

The CF2H group can act as a hydrogen bond donor, serving as a potential surrogate for OH or SH groups but with a weaker hydrogen bond donation ability. Here, we describe a series of CF2H group-containing moieties that facilitate hydrogen bond interactions. We survey hydrogen bond donation ability using several established methods, including 1H NMR-based hydrogen bond acidity determination, UV-vis spectroscopy titration with Reichardt's dye, and 1H NMR titration using tri-n-butylphosphine oxide as a hydrogen bond acceptor. Our experiments reveal that the direct attachment of the CF2H group to cationic aromatic systems significantly enhances its hydrogen bond donation ability, a result consistent with theoretical calculations. We anticipate that this chemistry will be valuable for designing functional molecules for chemical biology and medicinal chemistry applications.

量化CF2H基团作为氢键给体的能力。
CF2H可以作为氢键供体,作为OH或SH基团的潜在替代物,但其氢键供体能力较弱。在这里,我们描述了一系列促进氢键相互作用的含CF2H基团的片段。我们使用几种已建立的方法来研究氢键给予能力,包括基于1H核磁共振的氢键酸度测定,Reichardt染料的紫外-可见光谱滴定,以及使用三正丁基氧化膦作为氢键受体的1H核磁共振滴定。实验结果表明,CF2H基团直接附着在阳离子芳香体系上显著增强了其氢键给能能力,与理论计算结果一致。我们预计这种化学将在设计化学生物学和药物化学应用的功能分子方面具有价值。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
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.
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