The structural effect of heterocyclic amino compounds in liquid-liquid extraction using a calix[6]arene carboxylic acid derivative

Kojiro Shimojo, Tatsuya Oshima, Masahiro Goto

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The extraction behavior of heterocyclic compounds was investigated with a cyclic ligand calix[6]arene carboxylic acid derivative. Pyridine and pyrimidine bearing an amino group were quantitatively extracted with this host ligand. The presence of the amino group and the magnitude of pKa in the guest molecules significantly affect the extraction efficiency. The host ligand provides low extractability for guest molecules having a carbonyl group, which decreases the magnitude of pKa. The calix[6]arene carboxylic acid derivative exhibits a high extractability compared to other calix[6]arene derivatives and commercially available extractants. The important factors for extractants in obtaining high extractability were found to be the introduction of carboxylic acid groups and the inclusion effect of the macrocyclic structure. Among all nucleotide bases tested, the calix[6]arene carboxylic acid derivative showed the highest specificity for adenine.

Original languageEnglish
Pages (from-to)85-92
Number of pages8
JournalSolvent Extraction Research and Development
Volume11
Publication statusPublished - 2004

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Carboxylic Acids
Carboxylic acids
Derivatives
Ligands
Liquids
Bearings (structural)
Heterocyclic Compounds
Molecules
Adenine
Nucleotides
Pyridine
calix(6)arene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Filtration and Separation
  • Chemical Engineering(all)

Cite this

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abstract = "The extraction behavior of heterocyclic compounds was investigated with a cyclic ligand calix[6]arene carboxylic acid derivative. Pyridine and pyrimidine bearing an amino group were quantitatively extracted with this host ligand. The presence of the amino group and the magnitude of pKa in the guest molecules significantly affect the extraction efficiency. The host ligand provides low extractability for guest molecules having a carbonyl group, which decreases the magnitude of pKa. The calix[6]arene carboxylic acid derivative exhibits a high extractability compared to other calix[6]arene derivatives and commercially available extractants. The important factors for extractants in obtaining high extractability were found to be the introduction of carboxylic acid groups and the inclusion effect of the macrocyclic structure. Among all nucleotide bases tested, the calix[6]arene carboxylic acid derivative showed the highest specificity for adenine.",
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AU - Shimojo, Kojiro

AU - Oshima, Tatsuya

AU - Goto, Masahiro

PY - 2004

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N2 - The extraction behavior of heterocyclic compounds was investigated with a cyclic ligand calix[6]arene carboxylic acid derivative. Pyridine and pyrimidine bearing an amino group were quantitatively extracted with this host ligand. The presence of the amino group and the magnitude of pKa in the guest molecules significantly affect the extraction efficiency. The host ligand provides low extractability for guest molecules having a carbonyl group, which decreases the magnitude of pKa. The calix[6]arene carboxylic acid derivative exhibits a high extractability compared to other calix[6]arene derivatives and commercially available extractants. The important factors for extractants in obtaining high extractability were found to be the introduction of carboxylic acid groups and the inclusion effect of the macrocyclic structure. Among all nucleotide bases tested, the calix[6]arene carboxylic acid derivative showed the highest specificity for adenine.

AB - The extraction behavior of heterocyclic compounds was investigated with a cyclic ligand calix[6]arene carboxylic acid derivative. Pyridine and pyrimidine bearing an amino group were quantitatively extracted with this host ligand. The presence of the amino group and the magnitude of pKa in the guest molecules significantly affect the extraction efficiency. The host ligand provides low extractability for guest molecules having a carbonyl group, which decreases the magnitude of pKa. The calix[6]arene carboxylic acid derivative exhibits a high extractability compared to other calix[6]arene derivatives and commercially available extractants. The important factors for extractants in obtaining high extractability were found to be the introduction of carboxylic acid groups and the inclusion effect of the macrocyclic structure. Among all nucleotide bases tested, the calix[6]arene carboxylic acid derivative showed the highest specificity for adenine.

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