Proton‐Ionizable crown compounds. 8. Synthesis and structural studies of macrocyclic polyether ligands containing a 4‐thiopyridone subcyclic unit

Jerald S. Bradshaw, P. Huszthy, Hiroyuki Koyama, Steven G. Wood, Scott A. Strobel, Richard B. Davidson, Reed M. Izatt, N. Kent Dalley, John D. Lamb, James J. Christensen

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Three new proton‐ionizable macrocyclic polyether ligands containing the 4‐pyridone subcyclic group have been prepared. Two of these ligands contain lipophilic n‐octyl substituents, the other ligand contains a phenyl substituent. The 15‐crown‐5 ligand containing both a 4‐pyridone subcyclic unit and an n‐octyl substituent selectively transported lithium cations in a water‐methylene chloride‐water bulk liquid membrane system. Five crown compounds containing the 4‐pyridone subcyclic unit were converted to the 4‐thiopyridono‐crown compounds when treated with Lawesson's Reagent. The crystal structure of 4‐thiopyridono‐18‐crown‐6 shows a carbon‐sulfur double bond and a molecule of water hydrogen bonded inside the macrocycle cavity.

Original languageEnglish
Pages (from-to)1837-1843
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume23
Issue number6
DOIs
Publication statusPublished - 1986

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Crown Compounds
Polyethers
Ligands
2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
Liquid membranes
Lithium
Cations
Hydrogen
Crystal structure
Molecules
Water

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Proton‐Ionizable crown compounds. 8. Synthesis and structural studies of macrocyclic polyether ligands containing a 4‐thiopyridone subcyclic unit. / Bradshaw, Jerald S.; Huszthy, P.; Koyama, Hiroyuki; Wood, Steven G.; Strobel, Scott A.; Davidson, Richard B.; Izatt, Reed M.; Dalley, N. Kent; Lamb, John D.; Christensen, James J.

In: Journal of Heterocyclic Chemistry, Vol. 23, No. 6, 1986, p. 1837-1843.

Research output: Contribution to journalArticle

Bradshaw, Jerald S. ; Huszthy, P. ; Koyama, Hiroyuki ; Wood, Steven G. ; Strobel, Scott A. ; Davidson, Richard B. ; Izatt, Reed M. ; Dalley, N. Kent ; Lamb, John D. ; Christensen, James J. / Proton‐Ionizable crown compounds. 8. Synthesis and structural studies of macrocyclic polyether ligands containing a 4‐thiopyridone subcyclic unit. In: Journal of Heterocyclic Chemistry. 1986 ; Vol. 23, No. 6. pp. 1837-1843.
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AU - Wood, Steven G.

AU - Strobel, Scott A.

AU - Davidson, Richard B.

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