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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Veröffentlicht in: | Tetrahedron letters 2010-12, Vol.51 (50), p.6516-6520 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2010.10.012 |