Ammonium ion binding with pyridine-containing crown ethers

Theresa Chang, Aaron M. Heiss, Stuart J. Cantrill, Matthew C T Fyfe, Anthony R. Pease, Stuart J. Rowan, J. Fraser Stoddart, Andrew J P White, David J. Williams

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Dipyrido[24]crown-8 (DP24C8) has been synthesized and shown to form [2]pseudorotaxanes spontaneously with dibenzylammonium ions. These complexes, which have been demonstrated by 1H NMR spectroscopy to form faster in solution than when the macrocyclic polyether is dibenzo[24]crown-8 (DB24C8), are also stronger than their DB24C8 counterparts. One of the [2]pseudorotaxanes has been used to construct a [2]rotaxane (see above) comprising a dumbbell-shaped component based on a dibenzylammonium ion which is encircled by a DP24C8 macrocycle and terminated by (triphenylphosphonium)methyl stoppers.

Original languageEnglish
Pages (from-to)2947-2950
Number of pages4
JournalOrganic Letters
Volume2
Issue number19
Publication statusPublished - 2000 Sep 21
Externally publishedYes

Fingerprint

Rotaxanes
Crown Ethers
Ammonium Compounds
ethers
pyridines
Ions
Crowns
ions
Polyethers
nuclear magnetic resonance
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
spectroscopy
pyridine
dibenzo-24-crown-8

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Chang, T., Heiss, A. M., Cantrill, S. J., Fyfe, M. C. T., Pease, A. R., Rowan, S. J., ... Williams, D. J. (2000). Ammonium ion binding with pyridine-containing crown ethers. Organic Letters, 2(19), 2947-2950.

Ammonium ion binding with pyridine-containing crown ethers. / Chang, Theresa; Heiss, Aaron M.; Cantrill, Stuart J.; Fyfe, Matthew C T; Pease, Anthony R.; Rowan, Stuart J.; Stoddart, J. Fraser; White, Andrew J P; Williams, David J.

In: Organic Letters, Vol. 2, No. 19, 21.09.2000, p. 2947-2950.

Research output: Contribution to journalArticle

Chang, T, Heiss, AM, Cantrill, SJ, Fyfe, MCT, Pease, AR, Rowan, SJ, Stoddart, JF, White, AJP & Williams, DJ 2000, 'Ammonium ion binding with pyridine-containing crown ethers', Organic Letters, vol. 2, no. 19, pp. 2947-2950.
Chang T, Heiss AM, Cantrill SJ, Fyfe MCT, Pease AR, Rowan SJ et al. Ammonium ion binding with pyridine-containing crown ethers. Organic Letters. 2000 Sep 21;2(19):2947-2950.
Chang, Theresa ; Heiss, Aaron M. ; Cantrill, Stuart J. ; Fyfe, Matthew C T ; Pease, Anthony R. ; Rowan, Stuart J. ; Stoddart, J. Fraser ; White, Andrew J P ; Williams, David J. / Ammonium ion binding with pyridine-containing crown ethers. In: Organic Letters. 2000 ; Vol. 2, No. 19. pp. 2947-2950.
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