Complexation of diquat and paraquat by macrocyclic polyethers incorporating two dibydroxynaphthalene residues

Peter R. Ashtona*, Ewan J T Chrystal, John P. Mathias, Keith P. Parry, Alexandra M Z Slawin, Neil Spencer, J. Fraser Stoddart, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

83 Scopus citations

Abstract

NMR Spectroscopy and FAB mass spectrometry demonstrate that the 38-crown-10 (1/5DN38C10) and 35-crown-9 (1/5DN35C9) ethers incorporating two 1,5-di-naphtho units form 1:1 complexes with the Paraquat [PQT]2+ and Diquat [DQT]2+ dications in solution. In the solid state, the [PQT.1/5DN38C10]2+ complex is stabilised by face-to-face (π/π charge transfer) interactions between the naphtho and bipyridinium rings, whereas the free 1/5DN35C9 receptor features a classic edge-to-face (Hδ+/π electrostatic) interaction between its two naphtho rings.

Original languageEnglish (US)
Pages (from-to)6367-6370
Number of pages4
JournalTetrahedron Letters
Volume28
Issue number50
DOIs
StatePublished - 1987

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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