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Title: Mono-ionizable calix[4]arene-benzocrown-6 ligands in 1,3-alternate conformations: synthesis, structure and silver(I) extraction

Abstract

Two series of novel mono-ionizable calix[4]arene-benzocrown-6 ligands in 1,3-alternate conformations are synthesized. In one series, the proton-ionizable group (PIG) is attached to the para position of one aromatic ring in the calixarene framework, thereby positioning it over the polyether ring cavity. In the other series, the PIG is a substituent on the benzo group in the polyether ring. This orients the PIG away from the crown ether cavity. In addition to carboxylic acid functions, the PIGs include N-(X)sulfonyl carboxamide groups. With X group variation from methyl to phenyl to 4-nitrophenyl to trifluoromethyl, the acidity of the PIG is 'tuned'. Solvent extraction of Ag{sup +} from aqueous solutions into chloroform is used to probe the influence of structural variation within the mono-ionizable calixcrown ligand on metal ion extraction efficiency, including the identity and acidity of the PIG and its orientation with respect to the polyether ring.

Authors:
 [1];  [2]
  1. ORNL
  2. Texas Tech University, Lubbock
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
969009
DOE Contract Number:  
DE-AC05-00OR22725
Resource Type:
Journal Article
Journal Name:
Organic and Biomolecular Chemistry
Additional Journal Information:
Journal Volume: 65; Journal Issue: 37; Journal ID: ISSN 0040-4020
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; CALIXARENES; CROWN ETHERS; MOLECULAR STRUCTURE; VARIATIONS; PH VALUE; SOLVENT EXTRACTION; SILVER; SYNTHESIS; SOLVENT PROPERTIES

Citation Formats

Custelcean, Radu, and Bartsch, Richard A. Mono-ionizable calix[4]arene-benzocrown-6 ligands in 1,3-alternate conformations: synthesis, structure and silver(I) extraction. United States: N. p., 2009. Web.
Custelcean, Radu, & Bartsch, Richard A. Mono-ionizable calix[4]arene-benzocrown-6 ligands in 1,3-alternate conformations: synthesis, structure and silver(I) extraction. United States.
Custelcean, Radu, and Bartsch, Richard A. 2009. "Mono-ionizable calix[4]arene-benzocrown-6 ligands in 1,3-alternate conformations: synthesis, structure and silver(I) extraction". United States.
@article{osti_969009,
title = {Mono-ionizable calix[4]arene-benzocrown-6 ligands in 1,3-alternate conformations: synthesis, structure and silver(I) extraction},
author = {Custelcean, Radu and Bartsch, Richard A.},
abstractNote = {Two series of novel mono-ionizable calix[4]arene-benzocrown-6 ligands in 1,3-alternate conformations are synthesized. In one series, the proton-ionizable group (PIG) is attached to the para position of one aromatic ring in the calixarene framework, thereby positioning it over the polyether ring cavity. In the other series, the PIG is a substituent on the benzo group in the polyether ring. This orients the PIG away from the crown ether cavity. In addition to carboxylic acid functions, the PIGs include N-(X)sulfonyl carboxamide groups. With X group variation from methyl to phenyl to 4-nitrophenyl to trifluoromethyl, the acidity of the PIG is 'tuned'. Solvent extraction of Ag{sup +} from aqueous solutions into chloroform is used to probe the influence of structural variation within the mono-ionizable calixcrown ligand on metal ion extraction efficiency, including the identity and acidity of the PIG and its orientation with respect to the polyether ring.},
doi = {},
url = {https://www.osti.gov/biblio/969009}, journal = {Organic and Biomolecular Chemistry},
issn = {0040-4020},
number = 37,
volume = 65,
place = {United States},
year = {Thu Jan 01 00:00:00 EST 2009},
month = {Thu Jan 01 00:00:00 EST 2009}
}