Mercaptocalixarenes as Mercury(II) Extractors: Synthesis, Structural Analysis and Extraction Properties of Lipophilic Dimercaptocalix[4]arenes

Rao, P. Jayaprasad; Enger, Olivier; Graf, Ernest; Hosseini, Mir Wais; Cian, André De; Fischer, Jean

doi:10.1002/1099-0682(200007)2000:7<1503::aid-ejic1503>3.0.co;2-6

Cited by 29 publications

(11 citation statements)

References 11 publications

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“…Furthermore, L4 was found to be more effective than the other compounds in extracting Cu 2+ ions. These ligands, which are very effective in transferring the transition elements, particularly Ag + , Hg 2+ , Cu 2+ and Cr 3+ donot extract the alkali metal cations to a significant extent [28], in which pphenylazocalix [6]arene is used as ligand. This azocalix [6]arene is a molecule actually used in the heavy metal detection in the literature [29,30].…”

Section: Resultsmentioning

confidence: 99%

“…Despite the complexation of transition metal cations being favoured by the introduction of softer donor atoms, such as nitrogen [4,5], sulphur [6], or phosphorus [7], ligands with harder oxygen atoms also bind those cations. These calix[n]arenes bear phenoxy and carbonyl oxygens as the ligating sites, and include vic-dioximes [8,9], hydroxamates [10], amides [11], carboxylic acids [12], esters [13], and ketones [14].…”

Section: Introductionmentioning

confidence: 99%

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Transition metal cations extraction by ester and ketone derivatives of chromogenic azocalix[4]arenes

Taban

Deligöz

2008

Journal of Hazardous Materials

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Transition metal cations extraction by ester and ketone derivatives of chromogenic azocalix[4]arenes

Taban

Deligöz

2008

Journal of Hazardous Materials

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“…121,122 Two related lipophilic dithiocalix [4]arenes proved less amenable to the NKR step. 123 Thiocarbamoylation of 154 gave non-equilibrating mixtures of the 1,2-and 1,3-O-aryl dithiocarbamate conformers, and the triadduct, all of which were separated by chromatography. Not surprisingly, the NKR step required 340°C for three hours under vacuum to give 20-25% yields of the desired bis-adducts, with 40-50% yields of the mono-NKR adducts, and 25-40% recovery of unreacted starting materials.…”

Section: Figure 13mentioning

confidence: 99%

Mechanism and Application of the Newman-Kwart O→S Rearrangement of O-Aryl Thiocarbamates

Lloyd‐Jones¹,

Moseley²,

Renny³

2008

Synthesis

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This literature review focuses on the thermal rearrangement of O-aryl thiocarbamates to yield the corresponding S-aryl thiocarbamates: the Newman-Kwart rearrangement. The purpose of the review is to highlight the utility of the rearrangement which provides a key step in an efficient route to convert phenols into thiophenols. The scope of the Newman-Kwart rearrangement is illustrated by way of numerous examples of its application to the preparation of Ar-S species ranging from large-scale industrial processes through to the synthesis of complex organic molecules such as ligands and supramolecular structures. The review contains 238 references and covers just over 40 years of the literature, from the first reports of the rearrangement by Edwards and Pianka in 1965 up to mid-2007. 1 Introduction 2 The Newman-Kwart Rearrangement (NKR) 2.1 Background and History 2.2 Preparation of O-Aryl Thiocarbamates for NKR and Subsequent Cleavage 2.3 Mechanism of Rearrangement 2.4 Nonclassical Conditions for Rearrangement 2.5 Allylic and Benzylic Rearrangements 2.

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“…26 A specific Hg(II) extracting agent based on an analogue of TMTCA bearing only two SH groups has also been reported. 27 Recently, examples of coordination networks based on combinations of TMTCA appended with four pyridyl groups and a Hg(II) cation have been reported. 28 For the present study, the tecton 1, based on the tetramercaptotetrathiacalix [4]arene backbone equipped with four pyridyl coordinating sites, was chosen (Fig.…”

Section: Choice Of Tectons Metal Cations and Anionmentioning

confidence: 99%

Molecular tectonics: anion control of dimensionality and connectivity in meta-pyridyl appended tetramercaptotetrathiacalix[4]arene based silver coordination networks

et al. 2014

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The combination of the same organic tecton 1, a meta-pyridyl appended tetramercaptotetrathiacalix[4]arene in 1,3-alternate conformation offering four pyridyl units and eight thioether groups, with three silver salts AgX (X = BF4(-), NO3(-) and SbF6(-)) leads, under identical conditions (concentration, temperature and solvent system), to the formation of different silver coordination networks. Both the connectivity and the dimensionality of the three silver coordination networks depend on the nature of the anion used as a counter ion. Whereas the weakly coordinating BF4(-) anion does not participate in the formation of the non-tubular 1D coordination network, the coordinating NO3(-) anion is bound to the metal cation and this leads to the formation of a tubular 1D silver coordination network. In both cases, the eight S atoms of the tecton 1 do not take part in the binding of the cation. In marked contrast, when the SbF6(-) anion is used as a counter ion, the organic tecton 1 behaves as a tetrakismonodentate through its four meta-pyridyl moieties and as a bischelating unit of the SCCS type leading thus to the formation of a porous 3D diamondoid-type network.

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Mercaptocalixarenes as Mercury(II) Extractors: Synthesis, Structural Analysis and Extraction Properties of Lipophilic Dimercaptocalix[4]arenes

Cited by 29 publications

References 11 publications

Transition metal cations extraction by ester and ketone derivatives of chromogenic azocalix[4]arenes

Transition metal cations extraction by ester and ketone derivatives of chromogenic azocalix[4]arenes

Mechanism and Application of the Newman-Kwart O→S Rearrangement of O-Aryl Thiocarbamates

Molecular tectonics: anion control of dimensionality and connectivity in meta-pyridyl appended tetramercaptotetrathiacalix[4]arene based silver coordination networks

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