Premium
A New Cryptophane Receptor Featuring Three endo ‐Carboxylic Acid Groups: Synthesis, Host Behavior and Structural Study
Author(s) -
Roesky Christian E. O.,
Weber Edwin,
Rambusch Torsten,
Stephan Holger,
Gloe Karsten,
Czugler Mátyás
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390127
Subject(s) - lanthanide , carboxylic acid , chemistry , extraction (chemistry) , alkali metal , molecule , metal ions in aqueous solution , metal , alkaline earth metal , crystal structure , ion , crystallography , stereochemistry , inorganic chemistry , polymer chemistry , organic chemistry
Examples of a new type of cryptophane molecule incorporating aromatic groups in the bridges ( 1 – 4 ) and, for the first time, being also supplied with three endo ‐positional ionizable carboxylic acid functions ( 1 ) have been synthesized and characterized. The cryptophane triester 2 yielded a solvate (channel inclusion compound) with trichloromethane and water, the X‐ray crystal structure of which is reported. The complexation of 1 with low‐molecular‐weight alcohols in solution was studied, and the liquid–liquid extraction of different metal ions including alkali (Na + , Cs + ), alkaline earth (Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ ), and the lanthanide metal ions Eu 3+ and Yb 3+ in an extraction system containing metal nitrate buffer/H 2 O/ 1 /CHCl 3 was examined. Molecular modeling calculations of the cryptophanes 1 and 2 , and of the Eu 3+ complex of 1 were carried out contributing to the discussion.