Synthesis and extraction studies of a versatile calix[4]arene-based "proton-switchable extractant" for toxic metals and dichromate anions

The article describes the syntheses and extraction properties of a new calixarene based extractant 5, which has been synthesized from 5,11,17,23-tetra-tert-butyl-25,27-bis(chlorocarbonyl-methoxy)-26,28-dihydroxycalix[4]arene (4) by treatment with isoniazid (isonicotinic acid hydrazide) in the presen...

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Bibliographic Details
Published inJournal of inclusion phenomena and macrocyclic chemistry Vol. 45; no. 3-4; pp. 265 - 270
Main Authors Tabakci, M, Memon, S, Yilmaz, M, Roundhill, DM
Format Journal Article
LanguageEnglish
Published DORDRECHT Springer Nature 01.04.2003
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALKALI
ALKYLATION
solvent extraction
RHENIUM(I) BIPYRIDYL
dichromate anions
REDUCTION
alkali and transition metals
BINDING SITES
CROWN-ETHER
calixarene
CATION
COMPLEXATION
CHROMATE
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Summary:The article describes the syntheses and extraction properties of a new calixarene based extractant 5, which has been synthesized from 5,11,17,23-tetra-tert-butyl-25,27-bis(chlorocarbonyl-methoxy)-26,28-dihydroxycalix[4]arene (4) by treatment with isoniazid (isonicotinic acid hydrazide) in the presence of pyridine. The compound 5 was converted to its methyl iodide salt (6) by refluxing 5 with methyl iodide in acetonitrile. In this synthesis it was thought to explore the role of pyridinium sites in the extraction of HCr2O7-/Cr2O72- anions. The complexing properties of 5 toward selected alkali/transition metal cations and HCr2O7-/Cr2O72- anions are reported. It has been observed that receptor 5 does not extract alkali metal cations but shows an excellent selectivity toward transition metals. The protonated pyridinium form of 5 is an effective form for transferring the HCr2O7-/Cr2O72- anions from an aqueous into a dichloromethane layer.
ISSN:1388-3127
1573-1111