CaltechAUTHORS
  A Caltech Library Service

Synthesis of Novel Azamacrocyclic Metal Ion Receptors Using a Modified Mannich Aminomethylation Reaction

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

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20180406-091536308

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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/bk-1999-0716.ch008DOIArticle
https://pubs.acs.org/doi/abs/10.1021/bk-1999-0716.ch008PublisherArticle
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.
Funders:
Funding AgencyGrant Number
Department of Energy (DOE)DE-FG02-86ER 13463
Series Name:ACS Symposium Series
Issue or Number:716
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:03 Oct 2019 19:34

Repository Staff Only: item control page