Investigation of Imidazol(in)ium-dithiocarboxylates as Sensors for the Detection of Mercury(II) and Silver(I) Ions

Konieczna, Dagny Dagmara; Blanrue, Amélie; Wilhelm, René

doi:10.5560/znb.2014-4014

Cited by 13 publications

(4 citation statements)

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“…The dithiocarbamate structural moiety can be found in biologically active molecules widely applied as fungicides, herbicides, pesticides [21–25] and in some cases as enzyme inhibitors [26] or antitumor agents [27]. These species are also used as valuable synthetic intermediates [28] and chemosensors for mercury and silver [29–30].…”

Section: Introductionmentioning

confidence: 99%

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

Németh¹,

Keserü²,

Ábrányi‐Balogh³

2019

Beilstein J. Org. Chem.

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A new multicomponent reaction has been developed between isocyanides, sulfur and alcohols or thiols under mild reaction conditions to afford O-thiocarbamates and dithiocarbamates in moderate to good yields. The one-pot reaction cascade involves the formation of an isothiocyanate intermediate, thus a catalyst-free synthesis of isothiocyanates, as valuable building blocks from isocyanides and sulfur is proposed, as well. The synthetic procedure suits the demand of a modern organic chemist, as it tolerates a wide range of functional groups, it is atom economic and easily scalable.

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Section: Introductionmentioning

confidence: 99%

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

Németh¹,

Keserü²,

Ábrányi‐Balogh³

2019

Beilstein J. Org. Chem.

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“…Currently, the most general strategy to prepare NHC·CS 2 zwitterions relies on the deprotonation of an azolium salt with a strong base, typically potassium tert -butoxide or potassium bis(trimethylsilyl)amide (also known as potassium hexamethyldisilazide, KHMDS) followed by the addition of carbon disulfide either in one pot or after the isolation of the free carbene [ 39 , 41 – 42 58 ]. Hence, we decided to probe the feasibility of this approach for the synthesis of CAAC·CS 2 and MIC·CS 2 betaines from readily available aldiminium or 1,2,3-triazolium salts.…”

Section: Resultsmentioning

confidence: 99%

“…N-Heterocyclic carbenes and their enetetramine dimers readily add to the central carbon atom of allenes and heteroallenes X=C=Y (X, Y = CR 2 , NR, O, S) to afford zwitterionic adducts [29]. In particular, their reaction with carbon disulfide affords stable azolium-2-dithiocarboxylate zwitterions (Figure 2) [30][31][32][33][34][35][36][37][38][39][40][41][42][43]. These 1,1-dithiolate inner salts strongly bind main group elements and transition metals through various coordination modes.…”

Section: Introductionmentioning

confidence: 99%

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

Touj,

Mazars,

Zaragoza

et al. 2023

Beilstein J. Org. Chem.

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The synthesis of zwitterionic dithiocarboxylate adducts was achieved by deprotonating various aldiminium or 1,2,3-triazolium salts with a strong base, followed by the nucleophilic addition of the in situ-generated cyclic (alkyl)(amino) or mesoionic carbenes (CAACs or MICs) onto carbon disulfide. Nine novel compounds were isolated and fully characterized by 1H and 13C NMR, FTIR, and HRMS techniques. Moreover, the molecular structures of two CAAC·CS2 and two MIC·CS2 betaines were determined by X-ray diffraction analysis. The analytical data recorded for all these adducts were compared with those reported previously for related NHC·CS2 betaines derived from imidazolinium or (benz)imidazolium salts. Due to the absence of electronic communication between the CS2 unit and the orthogonal heterocycle, all the CAAC·CS2, MIC·CS2, and NHC·CS2 zwitterions displayed similar electronic properties and featured the same bite angle. Yet, their steric properties are liable to ample modifications by varying the exact nature of their cationic heterocycle and its substituents.

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“…N-Heterocyclic carbenes (NHCs) are powerful nucleophiles that react instantaneously with carbon disulfide to afford stable zwitterions conveniently designated as NHC·CS 2 adducts. , These inner salts are usually crystalline materials that form strong M–S bonds with a wide range of metal centers . Borer and co-workers first investigated their coordination chemistry in the 1980s by synthesizing various complexes from 1,3-dimethylimidazolium-2-dithiocarboxylate (IMe·CS 2 ) and diverse late transition metal halides or nitrates .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Biological Activity of Water-Soluble, Dual Anionic and Cationic Ruthenium–Arene Complexes Bearing Imidazol(in)ium-2-dithiocarboxylate Ligands

et al. 2021

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An efficient synthetic protocol was devised for the preparation of five cationic ruthenium−arene complexes bearing imidazol(in)ium-2-dithiocarboxylate ligands from the [RuCl 2 (pcymene)] 2 dimer and 2 equiv of an NHC•CS 2 zwitterion. The reactions proceeded cleanly and swiftly in dichloromethane at room temperature to afford the expected [RuCl(p-cymene)(S 2 C•NHC)]Cl products in quantitative yields. When the [RuCl 2 (p-cymene)] 2 dimer was reacted with only 1 equiv of a dithiolate betaine under the same experimental conditions, a set of five bimetallic compounds with the generic formulawas obtained in quantitative yields. These novel, dual anionic and cationic ruthenium−arene complexes were fully characterized by various analytical techniques. NMR titrations showed that the chelation of the dithiocarboxylate ligands to afford [RuCl(pcymene)(S 2 C•NHC)] + cations was quantitative and irreversible. Conversely, the formation of the [RuCl 3 (p-cymene)] − anion was limited by an equilibrium, and this species readily dissociated into Cl − anions and the [RuCl 2 (p-cymene)] 2 dimer. The position of the equilibrium was strongly influenced by the nature of the solvent and was rather insensitive to the temperature. Two monometallic and two bimetallic complexes cocrystallized with water, and their molecular structures were solved by X-ray diffraction analysis. Crystallography revealed the existence of strong interactions between the azolium ring protons of the cationic complexes and neighboring donor groups from the anions or the solvent. The various compounds under investigation were highly soluble in water. They were all strongly cytotoxic against K562 cancer cells. Furthermore, with a selectivity index of 32.1, the [RuCl(pcymene)(S 2 C•SIDip)]Cl complex remarkably targeted the erythroleukemic cells vs mouse splenocytes.

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Investigation of Imidazol(in)ium-dithiocarboxylates as Sensors for the Detection of Mercury(II) and Silver(I) Ions

Cited by 13 publications

References 0 publications

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

Synthesis, Characterization, and Biological Activity of Water-Soluble, Dual Anionic and Cationic Ruthenium–Arene Complexes Bearing Imidazol(in)ium-2-dithiocarboxylate Ligands

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