Anion and cation binding by a new indole/pyridine/amine-based ion-pair receptor

A new ion-pair receptor bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine ( 1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and 1H NMR spectroscopy. Among halides, 1 exhibits the strongest binding with Cl − to form a 1:1 adduct ( K a = 1042 ± 21 in CD 3CN). Amo...

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Bibliographic Details
Published in:Tetrahedron letters 2010-12, Vol.51 (50), p.6516-6520
Main Authors: Skala, Kristin N., Perkins, Katelyn G., Ali, Amna, Kutlik, Robert, Summitt, Addie M., Swamy-Mruthinti, Satyanarayana, Khan, Farooq A., Fujita, Megumi
Format: Article
Language:English
Subjects:
Alkali metals
Anion binding
Anions
Binding
Cation binding
Cations
ESI-MS
Indole
Ion-pair receptor
NMR spectroscopy
Nuclear magnetic resonance
Receptors
Titration
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Summary:A new ion-pair receptor bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine ( 1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and 1H NMR spectroscopy. Among halides, 1 exhibits the strongest binding with Cl − to form a 1:1 adduct ( K a = 1042 ± 21 in CD 3CN). Among alkali metal ions, Li + and Na + showed the strongest binding in the formation of a 1·M + complex. The simultaneous binding of Cl − and Li + to 1 was confirmed by 1H NMR titration of a 1:1 mixture of 1 and Cl − with LiPF 6 in 83:17 v/v mixture of CDCl 3 and DMSO- d 6. DFT-optimized structures of 1·Cl −, 1·Li +, and 1·Li +·Cl − are consistent with the chemical shift changes observed in 1H NMR studies.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.10.012