Synthesis of Novel Azamacrocyclic Metal Ion Receptors Using a Modified Mannich Aminomethylation Reaction
Abstract
A modified Mannich aminomethylation reaction was used to prepare a series of N-substituted-phenol-containing azacrown ether ligands. Ligands synthesized include aza-15-crown-5, aza-18-crown-6, azapyridino-18-crown-6, diaza-18-crown-6, diaza-21-crown-7 and diaza-24-crown-8 containing various substituted phenols, salicylaldehyde, and 5-chloro-8-hydroxyquinoline (CHQ) groups as side arms. The modified Mannich reaction was also used to prepare bi- and tricyclic azamacroheterocycles containing phenol units, benzoazacrown ethers, benzocryptands, and cryptohemispherands. The phenol- and CHQ-substituted azacrown ligands interact more strongly with metal ions than do the parent unsubstituted azacrown ethers. Bis-CHQ-substituted diaza-18-crown-6, wherein the CHQ groups are attached through their 7 positions, are particularly selective for K^+ over other alkali metal ions and for Ba^(2+) over all other metal ions studied.
Additional Information
© 1999 American Chemical Society. Published in print 11 February 1999. U. S. Department of Energy, Chemical Sciences Division, Office of Basic Energy Science, Contract no. DE-FG02-86ER 13463 provided funds for this work.Additional details
- Eprint ID
- 85679
- Resolver ID
- CaltechAUTHORS:20180406-091536308
- DE-FG02-86ER 13463
- Department of Energy (DOE)
- Created
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2018-04-06Created from EPrint's datestamp field
- Updated
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2021-11-15Created from EPrint's last_modified field
- Series Name
- ACS Symposium Series
- Series Volume or Issue Number
- 716