An ammonium/bis-ammonium switchable molecular shuttle

Leigh, D. A. and Thomson, A. R. (2008) An ammonium/bis-ammonium switchable molecular shuttle. Tetrahedron Letters, 64(36), pp. 8411-8416. (doi:10.1016/j.tet.2008.05.130)

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Abstract

A pH shuttle has been developed in which the mean position of the macrocycle can be switched between dialkylammonium stations of differing acidities. With only the most basic binding site protonated (dibenzylammonium), the macrocycle resides almost exclusively on the protonated station; when the second ammonium group (diethylammonium) is generated by further protonation, a mixture of translational diastereomers is observed in CD2Cl2 at 298 K, with the diethylammonium binding site preferred by the crown ether macrocycle in a ratio of ∼2:1.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Thomson, Dr Drew
Authors: Leigh, D. A., and Thomson, A. R.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron Letters
Publisher:Elsevier
ISSN:0040-4039
Published Online:05 June 2008

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