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Synthesis of N ‐octylmonoaza‐15‐crown‐5 having a dodecylphosphoric acid functional group and the binding ability toward alkali metal cations
Author(s) -
Habata Yoichi,
Akabori Sadatoshi
Publication year - 1994
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.5570310655
Subject(s) - chemistry , phosphoric acid , alkali metal , crown ether , inorganic chemistry , lithium (medication) , thiocyanate , phase (matter) , 15 crown 5 , sodium , hydroxide , ion , organic chemistry , medicine , endocrinology
A new N ‐octylmonoaza‐15‐crown‐5 having an alkylphosphoric acid functional group ( 3c ) was synthesized. It was revealed that 3c selectively transported sodium ion under neutral source phase/acidic receiving phase condition, and selectively transported lithium ion under basic source phase/acidic receiving phase condition. From an ir and 13 C nmr spectral study of the lithium hydroxide and sodium thiocyanate complexes of 3c , it is suggested that 3c does not incorporate cations into the three dimensional cavity using the crown ring and the phosphoric acid site, but that the crown and the phosphoric acid sites act on the cations independently; only the crown ether site of 3c significantly coordinates to the cations under neutral source phase condition, and the phosphate anion is mainly employed under basic conditions.