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Preparation of N ‐(4′,6′‐difluoro‐2′‐hydroxybenzyl)‐monoaza‐15‐crown‐5 and x‐ray crystal structure of potassium thiocyanate complex: A molecular partition wall
Author(s) -
Habata Yoichi,
Akabori Sadatoshi
Publication year - 2001
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.5570380226
Subject(s) - chemistry , potassium thiocyanate , ligand (biochemistry) , crystal structure , 15 crown 5 , thiocyanate , crown ether , mannich reaction , potassium , molecule , crystallography , medicinal chemistry , stereochemistry , polymer chemistry , inorganic chemistry , organic chemistry , ion , biochemistry , receptor , catalysis
Armed monoaza‐15‐crown‐5 having a 4′,6′‐difluoro‐2′‐hydroxybenzyl group as an additional binding site ( 2 ) has been prepared by the Mannich reaction of N ‐methoxymethylmonoaza‐15‐crown‐5 with 3,5‐difluorophenol. The reactive site on 3,5‐difluorophenol for the Mannich reaction was predicted by an electrostatic potential calculation (density functional calculation, SVWN/DN* method). Ligand 2 is interesting, because it has two possible binding sites (phenolic OH group and fluorine atom) in the side arm. An X‐ray crystal structure of the potassium thiocyanate complex of ligand 2 revealed that the oxygen atom of the phenolic OH group binds to the potassium cation incorporated in the crown ether ring, and two water molecules are enclosed by two armed crown ethers with the crown ethers forming partition walls.