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Deuterium exchange of pyrrolic NH protons accelerated by fluoride and bicarbonate in CDCl<sub>3</sub>, CD<sub>3</sub>CN, and DMSO-<i>d</i><sub>6</sub>
- Issue Date
- Jan-2025
- Publisher
- Royal Society of Chemistry
- Citation
- Organic Chemistry Frontiers, v.12, no.2, pp 599 - 606
- Pages
- 8
- Indexed
- SCIE
SCOPUS
- Journal Title
- Organic Chemistry Frontiers
- Volume
- 12
- Number
- 2
- Start Page
- 599
- End Page
- 606
- ISSN
- 2052-4110
2052-4129
- 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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