Fluorescent Lewis Adducts: A Practical Guide to Relative Lewis Acidity,Organometallics

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Fluorescent Lewis Adducts: A Practical Guide to Relative Lewis Acidity
Organometallics ( IF 2.5 ) Pub Date : 2020-10-15 , DOI: 10.1021/acs.organomet.0c00389
Jordan N. Bentley ₁ , Seja A. Elgadi ₁ , Joshua R. Gaffen ₁ , Paul Demay-Drouhard ₁ , Thomas Baumgartner ₁ , Christopher B. Caputo ₁

Affiliation

Experimentally determining the strength of a Lewis acid is a highly desirable and important task that has implications across the chemical sciences. Recently, we developed a new fluorescence-based method for evaluating the relative acidity of a small series of Lewis acids across the p- and d-blocks of the periodic table with great precision against a series of Lewis basic fluorescent dithienophosphole oxide probes. In this report, we considerably expand the scope of the fluorescent Lewis adduct method by systematically investigating the apparent acidities of more than 50 Lewis acids in toluene. Notably, a number of the investigated Lewis acids have never been experimentally measured before. Our refined guide, which now also alleviates the uncertainties that we identified with our original method, is simple and reliable. It shows extreme sensitivity to small structural or electronic perturbations and can account for coordinative flexibility or aggregation events that occur in solution, providing an alternative method for Lewis acidity determination that is complementary to the established nuclear magnetic resonance-based methods.

中文翻译：

荧光路易斯加合物：相对路易斯酸度的实用指南

通过实验确定路易斯酸的强度是一项非常理想且重要的任务，涉及整个化学科学领域。最近，我们开发了一种新的基于荧光的方法，可以相对于一系列Lewis碱性荧光二硫代磷酰氧化物探针，以极高的精度评估一小系列Lewis酸在元素周期表中p和d嵌段上的相对酸度。在本报告中，我们通过系统地研究甲苯中50多种路易斯酸的表观酸度，大大扩展了荧光路易斯加合物方法的范围。值得注意的是，许多研究过的路易斯酸以前从未进行过实验测量。我们完善的指南既简单又可靠，它现在还减轻了我们用原始方法确定的不确定性。

更新日期：2020-10-27

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