CN102207465A - Use of substituted mercaptothiodiazole compound in colorimetric identification of Hg<2+> - Google Patents
Use of substituted mercaptothiodiazole compound in colorimetric identification of Hg<2+> Download PDFInfo
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- CN102207465A CN102207465A CN2010105939978A CN201010593997A CN102207465A CN 102207465 A CN102207465 A CN 102207465A CN 2010105939978 A CN2010105939978 A CN 2010105939978A CN 201010593997 A CN201010593997 A CN 201010593997A CN 102207465 A CN102207465 A CN 102207465A
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Abstract
The invention discloses a use of substituted mercaptothiodiazole compound in colorimetric identification of Hg<2+>, belonging to the technical field of supermolecule. In accordance with colorimetric identification and ultraviolet-visible absorption spectrum study, the receptor compound has significant colorimetric identification effect for Hg<2+> in dimethyl sulfoxide containing 25% of water; meanwhile, the ultraviolet titration experiment also indicates that, the receptor has quite strong complexation ability for Hg<2+>; besides, the receptor has very high detection sensitivity for Hg<2+>, and the minimal detection limit can reach 1.5*10<-5>mol/L. Experiments also indicate that, the receptor compound has highly selective identification capability for Hg<2+> in a certain aqueous system, and has quite strong anti-interference ability for other metal ions. The receptor is adsorbed on filter paper and the filter paper is then air-dried to prepare cation test paper for the colorimetric detection of mercury ions in DMSO (dimethyl sulfoxide) solution, thus the characteristics of being convenient in carrying and use, high in detection sensitivity and the like are obtained.
Description
Technical field
The invention belongs to the supermolecule technical field, relate to a kind of substituted sulfhydryl thiadiazole compound and discern Hg in colorimetric as acceptor
2+In application.
Background technology
Mercury is a kind of chemical substance with height physiology toxicity, even in the lower level of content, it also is poisonous, the harmful environmental contaminants of a kind of height.And living in rivers and lakes and marine microbe and bacterium can make inorganic mercury become organic mercury, it can enter food chain easily and accumulate in the upper strata chain, after arriving human body, the people is produced serious feel sick, the damage of vomiting, stomachache and renal function, severe patient can damage people's brain and central nervous system, so very harmful.Therefore, it has become one of the most noticeable environmental contaminants in the present whole world.On the other hand, mercury and mercury salt use very extensive in industry again and pollute bigger.For these reasons, the detection of mercury has just caused people's very big concern in the environment, and constantly inquires into its detection method.Wherein particularly noticeable by the chemical sensitisation method of colorimetric or fluorescence molecule.Up to the present, people designed synthesized some can with Hg
2+The compound of selective binding is as the diethylamine of crown ether, calixarenes, polyamines and sulfur-bearing.But, can the selectivity colorimetric detect the also rarely seen report of acceptor of mercury ion.Simultaneously, the colorimetric detection mercury ion still needs obtain solution in the solution, and solution inconvenience is carried and preserved.Comparatively speaking, if develop the cationic test paper of energy colorimetric detection, will be more convenient for carrying, preserving and use.
The structure of substituted sulfhydryl thiadiazole compound contains N, the chromophore of N-3,5-dimethylphenyl, Schiff base, contain simultaneously-recognition group of SH, wherein the S in the recognition group has recognition reaction to mercury ion, so this compound can be used as the colorimetric identification receptor of mercury ion.The structural formula of substituted sulfhydryl thiadiazole compound is:
The mercaptan sulfur keto-acid
Above-mentioned thiol and thioketones formula are the simultaneous two kinds of tautomeric formulas of this receptor compound, are material of the same race.
Summary of the invention
The objective of the invention is to utilize the design feature of substituted sulfhydryl thiadiazole compound, provide a kind of this compound to discern Hg in colorimetric as acceptor
2+In application.
Another object of the present invention just provides and a kind ofly is adsorbed with the detection test paper of substituted sulfhydryl thiadiazole compound and at colorimetric detection Hg
2+In application.
Below by concrete experiment substituted sulfhydryl thiadiazole compound colorimetric is discerned Hg
2+Performance be described further.
Experimental apparatus and reagent:
1H NMR uses Mercury-400BB type nmr determination, and TMS is interior mark.Ultimate analysis uses Flash EA 1112 type elemental analysers to measure; IR uses Digilab FTS-3000 FT-IR type infrared spectrometer (KBr compressing tablet) to measure; Fusing point uses the X-4 numeral to show micro melting point apparatus (thermometer is not proofreaied and correct) mensuration; Ultraviolet spectrum uses Tianjin, island UV-2550 uv-visible absorption spectra instrument (the quartzy liquid pool of 1 cm) to measure.
Used kation is its perchlorate, and solvent is three distilled water and dimethyl sulfoxide (DMSO) (DMSO analyzes pure).It is pure that other reagent is commercially available analysis.
1, kation colorimetric recognition performance research
Pipette the DMSO solution (1 * 10 of 1.00 mL substituted sulfhydryl thiadiazole compounds respectively
-4MolL
-1) in a series of 10 mL color comparison tubes, three distilled water that pipette 1.25mL more respectively and then add Zn respectively in above-mentioned color comparison tube
2+, Pb
2+, Cd
2+, Ni
2+, Co
2+, Hg
2+, Ag
+, Ca
2+, Mg
2+, Cr
3+The DMSO solution (4 * 10 of perchlorate
-3MolL
-1) 0.25 ml.Be diluted to 5mL with DMSO, this moment, acceptor---the concentration of substituted sulfhydryl thiadiazole compound was 4 * 10
-5MolL
-1, the amount of cationic substance is 5 times (2 * 10 of amount of receptive material
-4MolL
-1), mix the back and placed about 30 minutes, observe acceptor substituted sulfhydryl thiadiazole compound to cationic response.Found that, when in the DMSO of acceptor solution, adding above-mentioned cationic DMSO solution respectively, Hg
2+Adding make the DMSO solution of acceptor significantly fade (taking off for colourless) by yellow.In its corresponding ultraviolet spectrum, Hg
2+Adding make acceptor at the absorption peak complete obiteration at 438nm place (see Fig. 1,2: ultraviolet spectrum and its histogram).All the other cationic addings do not have obvious influence to the DMSO solution colour and the ultraviolet spectrum of acceptor.Therefore, substituted sulfhydryl thiadiazole compound of the present invention can be used as acceptor selectivity colorimetric identification Hg in DMSO solution
2+
Experimental results demonstrate, at DMSO/H
2The O(water cut is 20 ~ 50%) system in, when the concentration of substituted sulfhydryl thiadiazole compound is 1 * 10
-4~ 4 * 10
-5MolL
-1The time, alternative colorimetric identification Hg
2+, promptly at the DMSO/H of substituted sulfhydryl thiadiazole compound
2The O(water cut is 20 ~ 50%) system in, Hg
2+Adding the DMSO system of acceptor is taken off for colourless by yellow.
2, ultraviolet titration
By the ultraviolet titration measuring acceptor compound---the substituted sulfhydryl thiadiazole compound is in conjunction with the complexation constant (Ks) of mercury ion, according to the least square method non-linear curve fitting, Ks=1.09 * 10 of substituted sulfhydryl thiadiazole compound complexing mercury ion
4, correlativity has reached 0.99.Illustrate that acceptor substituted sulfhydryl thiadiazole compound and mercury ion effect have formed stable complex.
3, interference free performance detects
In order to measure the detection effect of acceptor substituted sulfhydryl thiadiazole compound, carry out following test: the DMSO solution (1 * 10 that in three 10ml color comparison tubes, pipettes the 1.00mL this receptor respectively to mercury ion
-4MolL
1) and three distilled water of 1.25mL in above-mentioned color comparison tube, in one of them color comparison tube, add the mercury ion of 0.25mL, and then in another color comparison tube, add Zn
2+, Pb
2+, Cd
2+, Ni
2+, Co
2+, Hg
2+, Ag
+, Ca
2+, Mg
2+, Cr
3+Each 0.25mL is diluted to the 5mL scale with above-mentioned three color comparison tubes respectively with DMSO then; Three distilled water that pipette 2.5mL again are diluted to the 10mL scale with DMSO, as reference in the 10ml color comparison tube.Above-mentioned solution is mixed the back placement to be observed after 30 minutes.The results are shown in Figure 3.Acceptor is to Hg
2+Detection be not subjected to other cationic influence substantially.Above-mentioned solution left standstill was surveyed its uv-visible absorption spectra (DMSO makes reference) in 25 ℃ after 2 hours.Found that, add ten kinds of kations after, this receptor is in the equally also complete obiteration of absorption peak at 438nm place, this and Hg
2+To the influence of acceptor is consistently (to see Fig. 2 a-b: the ultraviolet spectrum histogram).Therefore, this receptor detects the interference that mercury ion is not subjected to other metal cation substantially.
4, to Hg
2+The mensuration of lowest detectable limit
At 25 ℃, utilize uv-visible absorption spectra, at this receptor (4 * 10
-5MolL
1) DMSO solution is to mercury ion (0.01 molL
1) titration experiments in, according to the volume of the mercury ion that is added and the design sketch of titration, can obtain the lowest detectable limit of this receptor to mercury ion.When adding concentration is the Hg of 0.1 times of acceptor
2+The time, faint sound is arranged in uv-visible absorption spectra, promptly this receptor is to Hg
2+Lowest detection be limited to 1.5 * 10
-5MolL
1
5, mercury ion detection paper and method of testing
For the ease of detecting identification Hg
2+, on acceptor load of substituted sulfhydryl thiadiazole compound and filter paper, obtain Hg
2+Detect test paper.
Hg
2+Detecting the preparation method of test paper, is to be 1 * 10 with filter paper in substituted sulfhydryl thiadiazole compound concentration
-4~ 4 * 10
-5MolL
-1, water cut 20 ~ 50% DMSO/H
2Soaked in the system of O 5 ~ 10 minutes, and took out, vacuum drying gets Hg
2+Detect test paper.
Hg
2+Detecting the application of test paper, is at Hg
2+Detecting and dripping concentration on the test paper is 1.5 * 10
-5~ 4 * 10
-3MolL
-1Cationic DMSO solution, filter paper is taken off for colourless by yellow, then the kation of Di Jiaing is Hg
2+
In sum, substituted sulfhydryl thiadiazole compound acceptor is recognition group with the dimercaptothiodiazole, to be the signal reporter group to dimethylamino phenyl, to Hg
2+Effectively discern.By colorimetric identification and uv-visible absorption spectra research, this receptor compound is to Hg
2+Significant colorimetric recognition effect is arranged; Show also that by the ultraviolet titration experiments this receptor is to Hg simultaneously
2+Very strong complexing power is arranged; And this receptor is to Hg
2+Detection sensitivity very high, lowest detectable limit can reach 1.5 * 10
-5MolL
-1Experiment is proof also, and this receptor compound is at DMSO/H
2The O(water cut is 20 ~ 50%) system in to Hg
2+Have the high selectivity recognition capability, and other metallic ion is had very strong antijamming capability.And made Hg
2+Detect test paper, this test paper is taken off for what colourless explanation dripped by yellow and is Hg
2+Solution.
Description of drawings
Fig. 1 for acceptor compound of the present invention in moisture 25% DMSO solution (4 * 10
5MolL
1) scheme with the uv-visible absorption spectra identification of various kations (5eqv)
Fig. 2 is the histogram of acceptor compound of the present invention to ten kinds of kation recognition effects
Wherein, 1 is the DMSO solution of this receptor compound moisture 25%
Fig. 3 for acceptor compound of the present invention during to mercury ion detecting other ten kinds of kations to the interference figure of this receptor
Fig. 4 for acceptor compound of the present invention during to mercury ion detecting other ten kinds of kations to the interference histogram of this receptor
Wherein, 1 is the DMSO solution of this receptor compound moisture 25%.
Embodiment
Below by preparation and the detection Hg thereof of specific embodiment to acceptor of the present invention
2+Method be described further.
The preparation of embodiment 1, substituted sulfhydryl thiadiazole compound
In three-necked bottle, the thiosemicarbazides of 1.1g is dissolved into 14 mL DMF(N, dinethylformamide), add the CS of 1.52g again
2, reflux about 6 hours until no longer producing H 80 ℃ of heated and stirred
2Till the S; Cooling, pressure reducing and steaming DMF are then with 35mL, 2molL
-1NaOH solution adds in the three-necked bottle, and be bronzing in the bottle this moment, uses 4 molL then
-1Concentrated hydrochloric acid be acidified to pH=1 ~ 2, the thick product of light-yellow precipitate, suction filtration, oven dry, the absolute ethyl alcohol recrystallization with 50% must light yellow acicular crystal 2-amino-5-sulfydryl-1,3, the 4-thiadiazoles.
In the round-bottomed flask of 500mL, add the paradime thylaminobenzaldehyde of 10mmol, 2-amino-5-sulfydryl-1,3 of 10mmol, the 4-thiadiazoles, the absolute methanol that adds 20mL again is as solvent; Add the 0.25ml glacial acetic acid then as catalyzer, about 80 ℃ of heated and stirred backflow 8h, get the Chinese red crude product, suction filtration, the absolute ethyl alcohol recrystallization is used in oven dry, gets Chinese red pulverulent solids compound.
Productive rate: 85%; M.p.240 ~ 241 oC;
1H-NMR (DMSO-d
6, 400 MHz) δ 14.25 (m, 1H, SH), 8.41 (s, 1H, CH), 7.81 (d, J=8.8,2H, ArH), 6.82 (d, J=8.8,2H, ArH), 3.07 (q, 6H, CH
3); IR (KBr, cm
-1)
v: 2888 (m, C-H), 1593 (s, C=N).
Embodiment 2, solution detect Hg
2+
Pipette the DMSO solution (1 * 10 of 1.00 mL substituted sulfhydryl thiadiazole compounds respectively
-4MolL
-1) in a series of 10 mL color comparison tubes, three distilled water that pipette 1.25mL more respectively are in above-mentioned color comparison tube; And then add Zn respectively
2+, Pb
2+, Cd
2+, Ni
2+, Co
2+, Hg
2+, Ag
+, Ca
2+, Mg
2+, Cr
3+The DMSO solution (4 * 10 of perchlorate
-3MolL
-1) 0.25 mL.Be diluted to 5mL with DMSO, mix the back and placed about 30 minutes.Taken off for colourless by yellow as solution colour, that then explanation adds is Hg
2+The DMSO solution of perchlorate; Do not have marked change as solution colour, what then explanation added is the DMSO solution of other cationic perchlorate.
Embodiment 3, detection paper Hg
2+
Substituted sulfhydryl thiadiazole compound acceptor is mixed with 0.01molL
1DMSO solution, the long 4cm of clip respectively then, ten of the filter paper of wide 1cm soaked into it in the DMSO solution of this substituted sulfhydryl thiadiazole compound acceptor 10 minutes, took out and place the vacuum drying chamber drying then.After drying is good filter paper is lain against in the 10cm plate, drip Zn respectively with dropper
2+, Pb
2+, Cd
2+, Ni
2+, Co
2+, Hg
2+, Ag
+, Ca
2+, Mg
2+, Cr
3+The DMSO solution (4 * 10 of perchlorate
-3MolL
-1), become colorless by yellow as the test paper color, that then drip is Hg
2+Solution; If the test paper color does not have significant change, then is other kation.
Claims (5)
1. the substituted sulfhydryl thiadiazole compound is discerned Hg as acceptor in colorimetric
2+In application.
2. the substituted sulfhydryl thiadiazole compound is discerned Hg as acceptor in colorimetric according to claim 1
2+In application, it is characterized in that: at the DMSO/H of water cut 20 ~ 50%
2In the system of O, the concentration of substituted sulfhydryl thiadiazole compound is 1 * 10
-4~ 4 * 10
-5MolL
-1The time, Hg
2+Adding make the DMSO/H of acceptor
2The O system is taken off for colourless by yellow.
3. Hg who is adsorbed with the substituted sulfhydryl thiadiazole compound
2+Detect test paper.
4. as being adsorbed with the Hg of substituted sulfhydryl thiadiazole compound as described in the claim 3
2+Detecting the preparation method of test paper, is to be 1 * 10 with filter paper in substituted sulfhydryl thiadiazole compound concentration
-4~ 4 * 10
-5MolL
-1, water cut 20 ~ 50% DMSO/H
2Soaked in the system of O 5 ~ 10 minutes, and took out, vacuum drying gets Hg
2+Detect test paper.
5. as being adsorbed with the Hg of substituted sulfhydryl thiadiazole compound as described in the claim 4
2+Detect the application of test paper, it is characterized in that: at Hg
2+Detecting and dripping concentration on the test paper is 1.5 * 10
-5~ 4 * 10
-3MolL
-1Cationic DMSO solution, filter paper is taken off for colourless by yellow, then the kation of Di Jiaing is Hg
2+
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105939978A CN102207465A (en) | 2010-12-17 | 2010-12-17 | Use of substituted mercaptothiodiazole compound in colorimetric identification of Hg<2+> |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105939978A CN102207465A (en) | 2010-12-17 | 2010-12-17 | Use of substituted mercaptothiodiazole compound in colorimetric identification of Hg<2+> |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103969430A (en) * | 2014-05-28 | 2014-08-06 | 甘肃农业大学 | Application of N-5 (2-mercapto-1, 3, 4-thiadiazole) phthalimide in detection of Hg2+and CN- |
| CN103969429A (en) * | 2014-05-28 | 2014-08-06 | 甘肃农业大学 | Application of N-5(2-sulfydryl-1,3,4-thiadiazole)p-phenyl diimine to detection of cyanide ions and copper ions |
| CN109342635A (en) * | 2018-09-29 | 2019-02-15 | 景宁畲族自治县食品药品检验检测中心 | A method of heavy metal in detection polygonatum cyrtonema |
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2010
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103969430A (en) * | 2014-05-28 | 2014-08-06 | 甘肃农业大学 | Application of N-5 (2-mercapto-1, 3, 4-thiadiazole) phthalimide in detection of Hg2+and CN- |
| CN103969429A (en) * | 2014-05-28 | 2014-08-06 | 甘肃农业大学 | Application of N-5(2-sulfydryl-1,3,4-thiadiazole)p-phenyl diimine to detection of cyanide ions and copper ions |
| CN103969430B (en) * | 2014-05-28 | 2016-02-03 | 甘肃农业大学 | Application of N-5 (2-mercapto-1, 3, 4-thiadiazole) phthalimide in detection of Hg2+and CN- |
| CN103969429B (en) * | 2014-05-28 | 2016-02-03 | 甘肃农业大学 | N-5 (2-sulfydryl-1,3,4-thiadiazoles) is detecting the application in cyanide ion, copper ion to benzene diimine |
| CN109342635A (en) * | 2018-09-29 | 2019-02-15 | 景宁畲族自治县食品药品检验检测中心 | A method of heavy metal in detection polygonatum cyrtonema |
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Application publication date: 20111005 |