Bradshaw, Jerald S. and Bordunov, Andrei V. and Zhang, Xian Xin and Pastushok, Victor N. and Izatt, Reed M. (1999) Synthesis of Novel Azamacrocyclic Metal Ion Receptors Using a Modified Mannich Aminomethylation Reaction. In: Metal-Ion Separation and Preconcentration. ACS Symposium Series. No.716. American Chemical Society , Washington, DC, pp. 133-144. ISBN 9780841235946. https://resolver.caltech.edu/CaltechAUTHORS:20180406-091536308
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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.
| Item Type: | Book Section | |||||||||
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| 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. | |||||||||
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| Series Name: | ACS Symposium Series | |||||||||
| Issue or Number: | 716 | |||||||||
| DOI: | 10.1021/bk-1999-0716.ch008 | |||||||||
| Record Number: | CaltechAUTHORS:20180406-091536308 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20180406-091536308 | |||||||||
| Official Citation: | Synthesis of Novel Azamacrocyclic Metal Ion Receptors Using a Modified Mannich Aminomethylation Reaction Jerald S. Bradshaw, Andrei V. Bordunov, Xian Xin Zhang, Victor N. Pastushok, and Reed M. Izatt Metal-Ion Separation and Preconcentration. February 11, 1999, 133-144 DOI:10.1021/bk-1999-0716.ch008 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 85679 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 06 Apr 2018 16:46 | |||||||||
| Last Modified: | 15 Nov 2021 20:31 |
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