Determination of the pKaH of Established Isothiourea Catalysts

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI:10.1002/ejoc.202401412

Lukas S. Vogl , Matthias Bechmann , Mario Waser

引用次数: 0

Abstract

Isothioureas (ITUs) represent a powerful family of (chiral) Lewis base organocatalysts. Interestingly, the Brønsted basicity of these frequently used compounds has so far not systematically been investigated. Thus, we have now determined the pK_aH values of the most privileged (chiral) ITUs in acetonitrile (ACN) and DMSO by using NMR. Employing Wallace's chemical shift imaging NMR method, the herein investigated ITUs were found to be weak Brønsted bases with pK_aH values in the range of 16.8–17.9 in ACN and 6.3–7.8 in DMSO.

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既定异硫脲催化剂pKaH的测定

异硫脲（ITUs）是一类强大的（手性）路易斯碱有机催化剂。有趣的是，到目前为止，这些常用化合物的Brønsted碱度尚未被系统地研究过。因此，我们现在通过核磁共振确定了乙腈（ACN）和DMSO中最特权的（手性）ITUs的pKaH值。采用Wallace 's化学位移成像核磁共振方法，发现本文所研究的化合物为弱br - nsted碱，其pKaH值在ACN中为16.8 ~ 17.9，在DMSO中为6.3 ~ 7.8。

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

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.