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Proton-ionizable crown compounds. 2. Synthesis, complexation properties, and structural studies of macrocyclic polyether-diester ligands containing a 4-hydroxypyridine subcyclic unit

Journal Article · · J. Org. Chem.; (United States)
OSTI ID:6303383
; ; ; ; ; ; ; ; ; ;
A series of macrocyclic polyether-diester ligands containing a proton-ionizable 4-hydroxypyridine subcyclic unit has been prepared. These new macrocyclic ligands form stable complexes with both alkylammonium perchlorate salts and with alkylamines. The crystal structure for one of these complexes with an alkylamine shows that the hydroxy proton has been donated to the amine with the resultant formation of a 4-pyridone unit. Chiral dimethyl- and diphenyl-substituted macrocycles containing the 4-hydroxpyridine subcyclic unit exhibit chiral recognition for the enantiomers of 2-(1-naphthyl)ethylamine and their hydrogen perchlorate salts. 15 references, 6 figures, 4 tables.
Research Organization:
Brigham Young Univ., Provo, UT
DOE Contract Number:
AC03-76SF00098; AC02-78ER05006
OSTI ID:
6303383
Journal Information:
J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 50:24; ISSN JOCEA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ACTIVATION ENERGY
ALCOHOLS
AZINES
BOND ANGLE
BOND LENGTHS
CHEMICAL PREPARATION
COHERENT SCATTERING
CRYSTAL STRUCTURE
DATA
DIFFRACTION
DIMENSIONS
ENERGY
ENTHALPY
EXPERIMENTAL DATA
GLYCOLS
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
INFORMATION
LENGTH
NMR SPECTRA
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC POLYMERS
PHYSICAL PROPERTIES
POLYETHYLENE GLYCOLS
POLYMERS
PYRIDINES
SCATTERING
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
THERMODYNAMIC PROPERTIES
X-RAY DIFFRACTION