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Proton‐Ionizable crown compounds. 8 . Synthesis and structural studies of macrocyclic polyether ligands containing a 4‐thiopyridone subcyclic unit
Author(s) -
Bradshaw Jerald S.,
Huszthy Peter,
Koyama Hiroyuki,
Wood Steven G.,
Strobel Scott A.,
Davidson Richard B.,
Izatt Reed M.,
Dalley N. Kent,
Lamb John D.,
Christensen James J.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230646
Subject(s) - chemistry , substituent , methylene , ligand (biochemistry) , reagent , 18 crown 6 , molecule , hydrogen bond , macrocyclic ligand , crystal structure , stereochemistry , polymer chemistry , medicinal chemistry , crystallography , organic chemistry , biochemistry , receptor
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.