Complexation and transport of transition and heavy metal cations by p-tert-butyldihomooxacalix[4]arene tetraketones and X-ray crystal structure of the tert-butyl ketone derivative

Marcos, Paula M.; Félix, Sandra; Ascenso, José R.; Segurado, Manuel A. P.; Thuéry, Pierre; Mellah, Besma; Michel, Sylvia; Hubscher-Bruder, Véronique; Arnaud‐Neu, Françoise

doi:10.1039/b705879a

Cited by 15 publications

(7 citation statements)

References 32 publications

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“…In the case of the transition and heavy metal cations, 3 is also a weak extractant, except for Ag + (18 % E). Although this cation is a soft Lewis acid [23], ligands bearing hard oxygen donor atoms (like calixcrowns) show usually a clear affinity for it, as has been observed by us for other derivatives [24,25].…”

Section: Extraction Studiessupporting

confidence: 69%

Synthesis, structural characterisation and metal ion-binding properties of a newp-tert-butyldihomooxacalix[4]crown-6

Marcos

Ascenso

2009

Supramolecular Chemistry

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Section: Extraction Studiessupporting

confidence: 69%

Synthesis, structural characterisation and metal ion-binding properties of a newp-tert-butyldihomooxacalix[4]crown-6

Marcos

Ascenso

2009

Supramolecular Chemistry

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“…It has been observed that the chemical shift changes of the methylene protons of the OCH 2 CO groups in dihomooxacalix [4]arene amide [26] and ketones [27,36] derivatives is upfield for the monovalent and downfield for the divalent cations. A closer examination of the spectral changes upon complexation indicates that triamide 1b behaves in a similar way.…”

Section: Proton Nmr Studiesmentioning

confidence: 98%

Binding Properties and Molecular Mechanics Calculations ofp-tert-Butylhexahomotrioxacalix[3]arene Tri(diethyl)amide with Alkali, Alkaline Earth, Transition and Heavy Metal Cations

Marcos

Ascenso²,

Cragg³

2007

Supramolecular Chemistry

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The binding of alkali, alkaline earth, transition (Mn 2 1 , Fe 2 1 , Co 2 1 , Ni 2 1 , Cu 2 1 and Zn 2 1 ) and heavy metal (Ag 1 , Cd 2 1 , Hg 2 1 and Pb 2 1 ) cations by cone p-tertbutylhexahomotrioxacalix[3]arene tri(diethyl)amide (1b) has been assessed by extraction studies of metal picrates from water to dichloromethane and proton NMR titration experiments. Molecular modelling techniques were also employed to complement the NMR data. The results are compared to those obtained with the dihomooxacalix[4]arene (2b) and calix[4]arene (3b) derivative analogues. Triamide 1b displays a high extracting ability towards Na 1 , Ba 2 1 , Ni 2 1 , Co 2 1 , Ag 1 and mainly Pb 2 1 (80% E). However, these values are lower than those obtained with tetraamides 2b and 3b, presumably due to the higher conformational flexibility of 1b. 1 H NMR titrations indicate the formation of 1:1 complexes between 1b and all the cations studied, and also that they should be located inside the cavity defined by the phenoxy and carbonyl oxygen atoms.

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“…Microcalorimetric titrations were performed at 25°C by using a 2277 Thermal Activity Monitor Microcalorimeter (Thermometric) according to the procedure already reported. [40] Heats of complexation were recorded after addition of 15 ϫ 15 µL aliquots of 10 -2  europium chloride in methanol on 2.7 mL of 1.0-1.5 ϫ 10 -4  ligand solutions in the same solvent. The enthalpy of complexation (∆H xy ) and the stability constants were refined simultaneously from these data after correction for the dilution by using the ligand binding analysis program DIGITAM version 4.1.…”

Section: Complexation Experimentsmentioning

confidence: 99%

Calix[6]arene‐Picolinamide Extractants for Radioactive Waste Treatment: Effect of Additional Carboxy Binding Sites in the Pyridine 6‐Positions on Complexation, Extraction Efficiency and An/Ln Separation

et al. 2010

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Keywords: Calixarenes / Actinides / Lanthanides / Waste treatment / N ligandsThe effect of the presence of an additional ester or amide carboxy group in the 6-position of the pyridine nuclei of calixarene-based picolinamide ligands on the extraction and complexation properties of lanthanide(III) and actinide(III) metal ions was studied. For this purpose, six new ligands 1-6 were synthesized; their conformational properties were studied both in solution and in the solid state, and their binding properties towards lanthanide (Ln III ) and actinide (An III ) metal ions were determined under extracting conditions simulating those present in radioactive waste. In the presence of BrCosan as synergizer, a rather high efficiency in the extrac-

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Complexation and transport of transition and heavy metal cations by p-tert-butyldihomooxacalix[4]arene tetraketones and X-ray crystal structure of the tert-butyl ketone derivative

Cited by 15 publications

References 32 publications

Synthesis, structural characterisation and metal ion-binding properties of a newp-tert-butyldihomooxacalix[4]crown-6

Synthesis, structural characterisation and metal ion-binding properties of a newp-tert-butyldihomooxacalix[4]crown-6

Binding Properties and Molecular Mechanics Calculations ofp-tert-Butylhexahomotrioxacalix[3]arene Tri(diethyl)amide with Alkali, Alkaline Earth, Transition and Heavy Metal Cations

Calix[6]arene‐Picolinamide Extractants for Radioactive Waste Treatment: Effect of Additional Carboxy Binding Sites in the Pyridine 6‐Positions on Complexation, Extraction Efficiency and An/Ln Separation

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