Deuterium Exchange of Pyrrolic NH Protons Accelerated by Fluoride and Bicarbonate in CDCl3, CD3CN, and DMSO-d6

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-18 DOI:10.1039/d4qo01855a

Sung Kuk Kim, Nam Jung Heo, Ju Hyun Oh, Jonathan L. Sessler

引用次数: 0

Abstract

The anion binding features of pyrrole- and benzene-strapped calix[4]pyrroles 1 and 2, in particular, for F^– and HCO₃^– have been examined by means of NMR spectroscopy in DMSO-d₆, CDCl₃, and CD₃CN, respectively. Receptors 1 and 2 were found to bind F^– and HCO₃^– tightly via slow binding/release equilibria in these solvents. A combination of ¹H and ¹⁹F NMR spectroscopic analyses with mass spectrometry revealed that contacting calix[4]pyrroles 1 and 2 with F^– and HCO₃^– salts prompts deuterium exchange of the NH protons in the three nominally aprotic deuterated solvents considered in this study.

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氟化物和碳酸氢盐加速 CDCl3、CD3CN 和 DMSO-d6 中吡咯烷 NH 质子的氘交换

在 DMSO-d6、CDCl3 和 CD3CN 中分别通过核磁共振光谱法研究了吡咯和苯束缚的卡利克[4]吡咯 1 和 2 的阴离子结合特征，特别是与 F- 和 HCO3- 的结合特征。研究发现，在这些溶剂中，受体 1 和 2 通过缓慢的结合/释放平衡与 F- 和 HCO3- 紧密结合。将 1H 和 19F NMR 光谱分析与质谱分析相结合发现，在本研究考虑的三种名义上氚代溶剂中，钙并[4]吡咯 1 和 2 与 F- 和 HCO3- 盐接触会促使 NH 质子发生氘交换。

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

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.