Hg(II) and Cd(II) complexes with mixed donor macrocyclic thioethers: The oxophobicity of mercury(II)

Grant, Gregory J.; Botros, Maikel; Hassler, Jared S.; Janzen, Daron E.; Grapperhaus, Craig A.; O’Toole, Martin G.; VanDerveer, Donald G.

doi:10.1016/j.poly.2008.07.005

Cited by 29 publications

(16 citation statements)

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“…Based on the TFCO having 9.7 mass% total S concentration, the average number of transformed thioether groups on each TAG structure was 3.85. It was expected that this abundance in thioether groups populating the TAG structures would facilitate the formation of M n + /oil complexes with coordination numbers of four to six as suggested in the literature (Cooper, ; Grant et al, ; Helm et al, ). This averages to one or two functionalized TAG molecules to bind a single M n + in the aqueous solution.…”

Section: Resultsmentioning

confidence: 92%

“…Second, M n + bind to the thioether pendant groups attached to the corn oil molecules forming complexes. This step involves chemisorption and reports in the literature (Cooper, ; Dance et al, ; Grant et al, ; Helm et al, ; Henkel et al, ; Love et al, ; Manceau et al, ) suggest that it is not the rate‐limiting step. Finally, complexes formed at the interface diffuse into the interior of the oil phase, leaving behind noncomplexed TFCO molecules to continue sorption in the first step.…”

Section: Resultsmentioning

confidence: 97%

“…Thioether complexes with Hg 2+ and Ag + contain different coordination numbers compared to their thiolate counterparts. Such complexes predominantly have a coordination number between four and six depending on the nature of the thioether and the steric bulk of the organic substituent (Cooper, ; Grant et al, ; Helm, Helton, VanDerveer, & Grant, ).…”

Section: Introductionmentioning

confidence: 99%

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Thioether‐Functionalized Corn Oil Biosorbents for the Removal of Mercury and Silver Ions from Aqueous Solutions

Dunn

Bantchev

Doll

et al. 2018

J Americ Oil Chem Soc

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Heavy-metal contamination is one of the most important environmental problems faced in the world, particularly in developing countries. Metals such as silver and mercury from drinking water, food, and air sources can accumulate in living organisms and present significant health concerns. Meanwhile, the demand for these metals in many industries continues to increase. In the present study, thioether-functionalized corn oil (TFCO) from a photoinitiated thiol-ene synthesis was utilized to remove Ag + and Hg 2+ ions from an aqueous solution. An aqueous solution containing AgNO 3 and Hg[NO 3 ] 2 was prepared and contacted directly with TFCO. After vortex mixing for 60 s, the experiment ran for 351 min with the aqueous phase being periodically sampled for the analysis of metal ions (M n+ ). Results showed that 88.9% of Ag + and 99.6% of Hg 2+ ions were removed from the aqueous phase by the TFCO. Mass balances indicated that the total M n+ concentration in the oil phase was 13.890 g kg −1 under the conditions studied. TFCO exhibited higher selectivity for removing Hg 2+ than for Ag + ions. Analysis of the adsorption kinetics showed that a pseudosecond-order model may be used to determine the rate of Ag + ion sorption by the oil phase. The presence of the Hg 2+ ions interfered with the adsorption of Ag + ions from the aqueous solution.Keywords Remediation Á Thioether-functionalized oil J Am Oil Chem Soc (2018) 95: 1189-1200. Abbreviations ICP-OESinductively coupled plasma-optical emission spectroscopy TFCO thioether-functionalized corn oil HPLC high performance liquid chromatography NMR nuclear magnetic resonance Symbols C 0 metal concentration in the aqueous phase before mixing with oil (mg kg −1 ) C e metal concentration in the aqueous phase at equilibrium (t ! ∞) (mg kg −1 )metal concentration in the aqueous phase at t (mg kg −1 ) k 2 pseudosecond-order adsorption rate constant (kg [mg min] −1 ) K D partition (distribution) coefficient at equilibrium (t ! ∞) m w mass of aqueous phase (g) M n+ metal ions m o mass of the TFCO phase (g) q [t] metal concentration in the oil phase at t (mg kg −1 ) q e metal concentration in the oil phase at equilibrium (t ! ∞) (mg kg −1 ) R 2 coefficient of correlation t time (min) σ y standard error of the y-estimate

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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Thioether‐Functionalized Corn Oil Biosorbents for the Removal of Mercury and Silver Ions from Aqueous Solutions

Dunn

Bantchev

Doll

et al. 2018

J Americ Oil Chem Soc

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“…The development of sensors for Hg 2+ usually involves the design and synthesis of molecules containing binding sites and a signaling subunit that has the ability to display selective changes in absorption or fluorescence spectra upon guest binding (22)(23)(24)(25)(26)(27)(28). It is reported that azathia macrocycle is generally thought to be a good receptor due to its strong ability to coordinate with heavy and transition metal ions such as Cu 2+ , Cd 2+ , Hg 2+ (29)(30)(31) and dansyl chloride is a classical fluorophore widely used in the development of fluorescent sensors due to its solvatochromism and high emission quantum yields (32)(33)(34). Additionally, intramolecular charge transfer (ICT) is an effective signaling mechanism employed in the design of fluorescent sensors (35)(36)(37)(38).…”

Section: Introductionmentioning

confidence: 99%

A highly selective fluorescent sensor for mercury ion (II) based on azathia‐crown ether possessing a dansyl moiety

et al. 2010

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An intramolecular charge transfer (ICT) fluorescent sensor 1 using a dansyl moiety as the fluorophore and an azathia-crown ether as the receptor was designed, synthesized and characterized. The ions-selective signaling behaviors of the sensor 1 were investigated in CH(3) CN-H(2) O (1:1, v/v) by fluorescence spectroscopy. It exhibited remarkable fluorescence quenching upon addition of Hg(2+), which was attributed to the 1:1 complex formation between 1 and Hg(2+), while other selected metal ions induced basically no spectral changes. The sensor 1 showed a rapid and linear response towards Hg(2+) in the concentration range from 5.0 × 10(-7) to 1.0 × 10(-5) mol L(-1) with the detection limit of 1.0 × 10(-7) mol L(-1). Furthermore, the whole process could be carried out in a wide pH range of 2.0-8.0 and was not disturbed by other metal ions. Thus, the sensor 1 was used for practical determination of Hg(2+) in different water samples with satisfactory results.

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“…Crystal structure of [Cd([9]aneOS 2 ) 2 ] 2+[205] The X-ray structure of the complex [Hg([9]aneOS 2 ) 2 ](ClO 4 ) 2 .2CH 3 NO 2 (Figure 99) shows that the four sulfur donors (two each per macrocycle) form a distorted tetrahedral environment, with the S-Hg-S bond angles ranging from 85.27(10)° to 141.68(10)°, with a median of 109.19(10)°, very close to an ideal tetrahedral value, around the fourcoordinate mercury centre [205]. The Hg-S bond distances average 2.596(3) Å and range from 2.547(3) Å to 2.649(3) Å; the two Hg-O distances (2.705(3) and 2.733(3) Å) indicate that the oxygen donors, oriented in an endodentate arrangement, are not coordinated to the Hg centre.…”

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confidence: 99%

Cyclononanes: The extensive chemistry of fundamentally simple ligands

Gahan

2016

Coordination Chemistry Reviews

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The cyclononane ligands are fundamental examples of the macrocyclic ligand. With three donor atoms in a nine-membered ring they represent the simplest of the macrocyclic class. However, this simplicity is deceptive, for within this class the variations are extensive and perhaps hitherto unrecognized. As well as the relatively familiar 1,4,7-triaza-([9]aneN 3) and 1,4,7-trithia-([9]aneS 3) cyclononanes whole families of cyclononane ligands are known with thioether/nitrogen, nitrogen/oxygen, selenium, tellurium as well as phosphorus and arsenic donors. The chemistry of some of these ligands, for example [9]aneN 2 S, [9]aneNS 2 and [9]aneN 2 O has been reported extensively, and some examples have simply been reported as having been synthesised (for example [9]aneO 2 S and [9]aneO 2 Se) with little other information. This review attempts to introduce the extensive chemistry of what are fundamentally the simplest examples of macrocyclic ligands. 1. Highlights Review of current trends in cyclononane chemistry Diversity of donor groups and transition metal chemistry complexes which arise Significant new synthetic chemistry Significant advances in the applications of cyclononane ligands

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Hg(II) and Cd(II) complexes with mixed donor macrocyclic thioethers: The oxophobicity of mercury(II)

Cited by 29 publications

References 46 publications

Thioether‐Functionalized Corn Oil Biosorbents for the Removal of Mercury and Silver Ions from Aqueous Solutions

Thioether‐Functionalized Corn Oil Biosorbents for the Removal of Mercury and Silver Ions from Aqueous Solutions

A highly selective fluorescent sensor for mercury ion (II) based on azathia‐crown ether possessing a dansyl moiety

Cyclononanes: The extensive chemistry of fundamentally simple ligands

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