Document Detail


A water-soluble calix[4]resorcinarene with L-pipecolinic acid groups as a chiral NMR solvating agent.
MedLine Citation:
PMID:  22278758     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A sulfonated calix[4]resorcinarene containing L-pipecolinic acid groups is investigated as a water-soluble chiral NMR solvating agent. Aromatic substrates with phenyl, indole, indane, naphthyl, and pyridyl rings are analyzed. The substrates, which are water soluble because of ammonium, hydroxyl, or carboxylate functional groups, form host-guest complexes by insertion of the aromatic ring into the cavity of the calix[4]resorcinarene. Enantiomeric discrimination with the calix[4]resorcinarene derivative with L-pipecolinic acid is compared with similar reagents with proline, hydroxyproline, and α-methylproline moieties that have previously been reported. The derivative with L-pipecolinic acid often produces the best enantiomeric discrimination for one or more hydrogen atoms of the 24 substrates examined herein. Chirality, 2012. © 2012 Wiley Periodicals, Inc.
Authors:
Ngoc H Pham; Thomas J Wenzel
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-1-25
Journal Detail:
Title:  Chirality     Volume:  -     ISSN:  1520-636X     ISO Abbreviation:  -     Publication Date:  2012 Jan 
Date Detail:
Created Date:  2012-1-26     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8914261     Medline TA:  Chirality     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2012 Wiley Periodicals, Inc.
Affiliation:
Department of Chemistry, Bates College, Lewiston, Maine.
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