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. 2006 Nov 15;128(45):14464-5.
doi: 10.1021/ja0657915.

Molecular recognition and stabilization of iminium ions in water

Vy M Dong  1 , Dorothea Fiedler, Barbara Carl, Robert G Bergman, Kenneth N Raymond
Affiliations

Molecular recognition and stabilization of iminium ions in water

Vy M Dong et al. J Am Chem Soc. .

Abstract

Iminium ions are known to exist only transiently in aqueous solution due to their high reactivity toward hydrolysis. In this communication, we report on the generation and stabilization of iminium ions in aqueous solution via molecular encapsulation using a K12Ga4L6 host. Our studies revealed that tetrahedral host 1 can encapsulate a variety of iminium cations in a molecular recognition process that is selective based on the charge, hydrophobicity, size, and shape of the guest.

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Figures

Figure 1
Figure 1
(Left) CAChe model of [Pr4N+ ⊂ Ga4L6]11− assembly; showing the Δ,Δ,Δ,Δ isomer. (Right) General schematic of the [Ga4L6]12− tetrahedron. One ligand is drawn while the additional ligands are represented by lines.
Scheme 1
Scheme 1
Stabilization of iminium ions in aqueous solution by molecular encapsulation.
Scheme 2
Scheme 2
Competition experiment between amines.
Scheme 3
Scheme 3
Competition experiment between 2-, 3-, and 4-heptanone.
See this image and copyright information in PMC

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