Heavy metal complexation by N-acyl(thio)urea-functionalized cavitands: synthesis, extraction and potentiometric studies

García, M. Martínez; Verboom, Willem; Reinhoudt, David N.; Malinowska, Elżbieta; Pietrzak, Mariusz; Wojciechowska, Dorota

doi:10.1016/j.tet.2004.08.044

Cited by 17 publications

(4 citation statements)

References 38 publications

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“…All the N-acyl(thio)urea derivatives show a high preference for Ag + , especially thiourea 8, the extraction value (84 %) of which is comparable to those obtained with N-acylthiourea-tetrafunctionalized cavitands and sulphur-containing calix [4]arene-based ionophores. [26] In the case of the cavitands there is a large difference in the extraction profile of acylthioureas vs. acylureas, but, the tripodal systems do not show this difference. There is a larger difference between the two N-acylthiourea derivatives (7 vs. 8) than between thiourea 7 and urea 9 ( Figure 1).…”

Section: Picrate Extractionsmentioning

confidence: 97%

Metal Complexation by Tripodal N‐Acyl(thio)urea and Picolin(thio)amide Compounds: Synthesis/Extraction and Potentiometric Studies

et al. 2005

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The synthesis and binding properties towards different cations of a series of tripodal ligands functionalized with N-acyl-(thio)urea and picolin(thio)amide moieties are described. For the extraction of Am 3+ and Eu 3+ the compounds are not efficient. However, N-acylurea derivative 10 exhibit a significant selectivity for Am 3+ over Eu 3+ . Upon addition of the synergistic hexabrominated bis(dicarbollide)cobalt anion (Br 6 -COSAN) the distribution coefficients for Am 3+ and Eu 3+ in-

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Section: Picrate Extractionsmentioning

confidence: 97%

Metal Complexation by Tripodal N‐Acyl(thio)urea and Picolin(thio)amide Compounds: Synthesis/Extraction and Potentiometric Studies

et al. 2005

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“…The formation of complexes with transition metal cations is favored in the presence of soft donor atoms such as nitrogen‐, sulfur‐, or phosphorus‐containing ligands . Acylthiourea, simultaneously bearing O, N, N′, and S donor atoms within the C(O)NHC(S)N skeleton, leads to a wide structural diversity in binding modes of their metal complexes .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Copper Complexes with the N‐(2,6‐Diisopropylphenyl)‐N′‐acylthiourea Ligands

Wang

et al. 2017

Eur J Inorg Chem

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Three N-(2,6-diisopropylphenyl)-N′-acylthiourea ligands [Ar′NHC(S)NHC(O)Ar; Ar′ = 2,6-iPr 2 C 6 H 3 ; Ar = p-tBuC 6 H 4 (1, L 1 ), Mes (2, L 2 ), and 1-Naph (3, L 3 )] were synthesized and compared with the homologous ligand L 0 (Ar = Ph) in terms of their resultant complexes with copper halides. The reaction of L 1 with CuCl 2 led to the formation of mononuclear L 1 2 CuCl (4), while treatment of L 1 with CuX (X = Cl, Br) resulted in the adamantane cage complexes (L 1 CuX) 4 (X = Cl, 5; Br, 6). These findings are similar to the results shown by its parent ligand L 0 .

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“…1). [12,18,19] In order to study the influence of a longer spacer between the platform and the ligating site in the case of CMP(O)-tetrafunctionalized cavitands, tetrakis(aminopropoxy) cavitand (9) [19] was reacted with chloroacetyl chloride in the presence of Et 3 N in dichloromethane to give cavitand 10 in 50% yield (Scheme 1). In the 1 H NMR spectrum a new signal at d 4.07 appears which belongs to the 2CH 2 Cl group and the methylene group adjacent to the nitrogen shifts from d 3.25 in 9 to d 3.56 in 10.…”

Section: Synthesismentioning

confidence: 99%

Solvent Extraction of Actinides and Lanthanides by CMP(O)‐ andN‐Acyl(thio)urea‐tetrafunctionalized Cavitands: Strong Synergistic Effect of Cobalt Bis(dicarbollide) Ions

Reinoso-García

Verboom

Reinhoudt

2005

Solvent Extraction and Ion Exchange

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The synthesis of two carbamoylmethylphosphate (CMP)-and -phosphine oxide (CMPO)-tetrafunctionalized cavitands with a propyl spacer between the cavitand platform and the chelating sites is described. Liquid-liquid extractions with CMP(O)-and N-acyl(thio)urea-tetrafunctionalized cavitands were performed from aqueous nitric acid into dichloromethane or o-nitrophenyl hexyl ether (NPHE). The extraction of americium (III) and europium (III) from aqueous nitric acid into NPHE was studied in both the absence and presence of Br 6 -COSAN as a synergist. CMP(O) cavitands are more efficient extractants than the corresponding Nacyl(thio)urea derivatives, whereas the latter ones show an interesting selectivity for americium (III) over europium (III) in the presence of Br 6 -COSAN. The introduction of a propyl chain between the cavitand platform and the chelating groups increases the

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Heavy metal complexation by N-acyl(thio)urea-functionalized cavitands: synthesis, extraction and potentiometric studies

Cited by 17 publications

References 38 publications

Metal Complexation by Tripodal N‐Acyl(thio)urea and Picolin(thio)amide Compounds: Synthesis/Extraction and Potentiometric Studies

Metal Complexation by Tripodal N‐Acyl(thio)urea and Picolin(thio)amide Compounds: Synthesis/Extraction and Potentiometric Studies

Synthesis and Characterization of Copper Complexes with the N‐(2,6‐Diisopropylphenyl)‐N′‐acylthiourea Ligands

Solvent Extraction of Actinides and Lanthanides by CMP(O)‐ andN‐Acyl(thio)urea‐tetrafunctionalized Cavitands: Strong Synergistic Effect of Cobalt Bis(dicarbollide) Ions

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