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Thiosemicarbazide compound, synthesis method and application to colorimetric detection of mercury ions

A technology of thiosemicarbazide and compounds, which is applied in the fields of analyzing materials through chemical reactions, analyzing materials through observing the influence of chemical indicators, organic chemistry, etc., to achieve the effect of good cation recognition ability

Inactive Publication Date: 2010-02-24
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, receptors capable of selective colorimetric detection of mercury ions have not been reported

Method used

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  • Thiosemicarbazide compound, synthesis method and application to colorimetric detection of mercury ions
  • Thiosemicarbazide compound, synthesis method and application to colorimetric detection of mercury ions
  • Thiosemicarbazide compound, synthesis method and application to colorimetric detection of mercury ions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Synthesis of acceptor 1-nitrophenyl-4-ethoxycarbonylthiosemicarbazide (Y1)

[0039] Dissolve 10mmol of ethyl chloroformate into 20mL of ethyl acetate, add 12mmol of potassium thiocyanate, 0.1mL of N,N,N',N'-tetramethylethylenediamine (TMEDA) as a catalyst, and stir the reaction at room temperature 5 hours. Filter to remove inorganic salts to obtain a solution of the intermediate ethoxycarbonyl isothiocyanate. Add 9.5 mmol of 4-nitrophenylhydrazine to this solution, stir and react at room temperature for 5 hours, and a precipitate is formed. Most of the solvent was distilled off under reduced pressure, and stood at room temperature for 3 hours. The precipitate was filtered and recrystallized with absolute ethanol to obtain crystals of the product Y1. The synthetic route is as follows:

[0040]

[0041] Y1: Yield: 89.7%; m.p.168~170℃; 1 H-NMR (DMSO-d 6 , 400MHz) δ11.32(s, 1H, NH), 11.24(s, 1H, NH), 9.46(s, 1H, NH), 8.08(d, J=9.2, 2H, ArH), 6.79(q, J =7.2, 2H,...

Embodiment 2

[0045] (1) Synthesis of acceptor 1-nitrophenyl-4-benzoylthiosemicarbazide (Y2)

[0046] Dissolve 10mmol of benzoyl chloride in 20mL of dichloromethane, add 12mmol of ammonium thiocyanate, 0.1mL of polyethylene glycol-400 (PEG-400) as a catalyst, and stir at room temperature for 5 hours. Filter to remove inorganic salts to obtain a solution of the intermediate benzoyl isothiocyanate. Add 9.5 mmol of 4-nitrophenylhydrazine to this solution, stir and react at room temperature for 5 hours, and a precipitate is formed. Most of the solvent was evaporated under reduced pressure, and the precipitate was left to stand at room temperature for 3 hours. The precipitate was filtered and recrystallized with anhydrous acetonitrile to obtain crystals of the product Y2. The synthetic route is as follows:

[0047]

[0048] Y2: Yield: 95.7%; m.p.199~201℃; 1 H-NMR (DMSO-d 6 , 400MHz) δ12.02 (s, 2H, NH), 9.77 (s, 1H, NH), 8.11-6.93 (m, 9H, ArH); IR (KBr, cm -1 )v: 3444(mb, N-H), 3310(m, N-...

Embodiment 3

[0052] (1) Synthesis of acceptor 1,3-dinitrophenyl-4-ethoxycarbonylthiosemicarbazide (Y3)

[0053] Dissolve 10mmol of ethyl chloroformate into 20mL of ethyl acetate, add 12mmol of potassium thiocyanate, 0.1mL of N,N,N',N'-tetramethylethylenediamine (TMEDA) as a catalyst, and stir the reaction at room temperature 5 hours. Filter to remove inorganic salts to obtain a solution of the intermediate ethoxycarbonyl isothiocyanate. Add 9.5 mmol of 2,4-dinitrophenylhydrazine to this solution, stir and react at room temperature for 5 hours, and a precipitate is formed. Most of the solvent was evaporated under reduced pressure, and the precipitate was left to stand at room temperature for 3 hours. The precipitate was filtered and recrystallized with absolute ethanol to obtain crystals of the product Y3. The synthetic route is as follows:

[0054]

[0055] Y3: Yield: 96.5%; m.p.208~210°C; 1H NMR (DMSO-d6, 400MHz) δ11.49(s, 2H, NH), 10.44(s, 1H, NH), 8.88(s, 1H, ArH ), 8.37~8.33(m, ...

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Abstract

The invention discloses a thiosemicarbazide compound with the colorimetric identification capability of Hg<2+> and Ag<+>. The compound uses a thiosemicarbazide group as an identification group and nitrobenzophenone as a signal-reporting group and can rapidly and accurately detect mercury ions and silver ions. The identification function of the thiosemicarbazide compound in dimethyl sulfoxide (DMSO) and ten kinds of positive ions are considerate by element synthesis and IR and <1>HNMR confirmation through colorimetric identification and ultraviolet-visible absorption spectrum, the result showsthat the compound can better performs the colorimetric identification on the Hg<2+> and the Ag<+>. Proved by ultraviolet titration experiments, the compound has stronger bonding capability to the Hg<2+> and higher detection sensitivity to the Hg<2+> and achieves a lowest detection limit of 1.6*10<-7> mol*L<-1>. In addition, experiments prove that the compound has selective identification capability to the Hg<2+> and has a certain anti-interference capability to other metal ions.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a thiosemicarbazide compound and a synthesis method thereof; at the same time, the invention also relates to an application of the thiosemicarbazide compound as an acceptor in colorimetric detection of mercury ions. Background technique [0002] Mercury is a chemical substance with severe physiological toxicity, and even at low concentrations, it is a highly toxic and harmful environmental pollutant. Bacteria living in rivers, lakes and oceans can turn inorganic mercury into methylmercury, which can easily enter the food chain and accumulate in the upper chain. After reaching the human body, it can cause severe nausea, vomiting, abdominal pain, and kidney damage, and It can damage the human brain and central nervous system, which is extremely harmful. Therefore, it has become one of the most concern environmental pollutants in the world. On the other hand, mercury and ...

Claims

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Application Information

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IPC IPC(8): C07C337/06G01N21/78
Inventor 魏太保俞梅林奇张有明
Owner NORTHWEST NORMAL UNIVERSITY
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