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Deuterium Exchange of Pyrrolic NH Protons Accelerated by Fluoride and Bicarbonate in CDCl3, CD3CN, and DMSO-d6
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-11-18 , DOI: 10.1039/d4qo01855a
Sung Kuk Kim, Nam Jung Heo, Ju Hyun Oh, Jonathan L. Sessler

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.

中文翻译:


在 CDCl3、CD3CN 和 DMSO-d6 中,氟化物和碳酸氢盐加速吡咯 NH 质子的氘交换



吡咯和苯绑的 calix[4]吡咯 12,特别是对 F 和 HCO3 的阴离子结合特性已分别通过 DMSO-d 6、CDCl3 和 CD3CN 的 NMR 波谱进行了检查。发现受体 12 通过这些溶剂中的缓慢结合/释放平衡紧密结合 F 和 HCO3-1H 和 19F NMR 波谱分析与质谱相结合表明,calix[4]pyrroles 12 与 F 和 HCO3- 盐接触会促使 NH 质子在本研究中考虑的三种名义上的非质子氘酸盐溶剂中发生氘交换。
更新日期:2024-11-18
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