CN102207455A - An open hole identification method for anions F -, ac - and H2PO4- - Google Patents

An open hole identification method for anions F -, ac - and H2PO4- Download PDF

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CN102207455A
CN102207455A CN2011100837258A CN201110083725A CN102207455A CN 102207455 A CN102207455 A CN 102207455A CN 2011100837258 A CN2011100837258 A CN 2011100837258A CN 201110083725 A CN201110083725 A CN 201110083725A CN 102207455 A CN102207455 A CN 102207455A
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朱丽君
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Abstract

The invention provides a method for detecting and identifying anions of F <->, Ac <-> and H2PO4 <-> through adopting an N-phenyl-N'-(2-acetoxylbenzoyl) thiourea derivative as a receptor. The method is characterized in that F <->, Ac <->and H2PO4 <-> are added into dimethylsulphoxide (DMSO) or a DMSO/H2O solution to make the solution have a color change from colorless to yellow, and there is not a color change when other anions are added into the solution, thus a unaided eye detection of F <->, Ac <-> and H2PO4 <-> is realized.

Description

A kind of negative ion F -, Ac -And H 2PO 4-The bore hole recognition methods
Technical field
The invention belongs to the detection technique field, relate to a kind of negative ion F -, Ac -And H 2PO 4 -The bore hole recognition methods, relate in particular to a kind of with N-phenyl- N'-(2-acetoxy benzoyl) thiourea derivative is acceptor bore hole identification negative ion F -, Ac -And H 2PO 4 -Method.
Technical field
Along with negative ion is being played the part of more and more important role in many research fields such as environment and biological medicine, anionic detection had crucial meaning.Therefore, have than strong affinity and optionally the colorimetric identification receptor become the interested field of present supramolecular chemistry researcher.Wherein, in many anion receptors, thiourea derivatives is the neutral acceptor molecule of a class that is most widely used, and it mainly is by hydrogen bond, and promptly the N-H group in the acceptor reaches the purpose that combines with negative ion as recognition site.Simultaneously, in fields such as the environment of reality and life sciences, Anion Recognition is carried out at aqueous phase mostly, and in protonic solvent (as aqueous solution), because solvent effect has weakened the interaction of hydrogen bond between the Subjective and Objective, limited the application extension of Anion Recognition research field, therefore, synthesize in aqueous solution or even pure aquatic system and can bore hole discern anionic new receptor, become research focus with actual application value.
F -, Ac -And H 2PO 4 -In environment and biological medicine, have consequence Deng negative ion, thereby, to F -, Ac -And H 2PO 4 -The detection of ion has crucial meaning.Along with going deep into of Anion Recognition research, although some detection methods by means of fluorescence, ultra-violet absorption spectrum etc. are also arranged, but the most receptors molecule all can only carry out in the non-protonic solvent under the anhydrous condition to anionic recognition reaction as azo analog derivative, hydrazone analog derivative, anthraquinone derivatives at present, and this has just greatly limited the range of application to Anion Recognition research.
Summary of the invention
The purpose of this invention is to provide a kind of with N-phenyl- N'-(2-acetoxy benzoyl) thiourea derivative is acceptor open hole detection identification negative ion F -, Ac -And H 2PO 4 -Method.
N-phenyl- N'The structure of-(2-acetoxy benzoyl) thiourea derivative is as follows:
Figure 56999DEST_PATH_IMAGE001
N-phenyl- N'-(2-acetoxy benzoyl) thiourea derivative synthetic as follows: the solid phosgene of homemade acetylsalicylic acid of 5 mmol and 5 mmol is placed 100 ml flasks, add 10 ml acetone and make solvent, drip 2 again N, N-dimethyl formamide is made catalyzer, and 2 h that reflux about 60 ℃ make intermediate.After the cool to room temperature, directly add the ammonium thiocyanate of 5.5 mmol porphyrizes again in flask, and Dropwise 5 drips PEG-400 and make phase transfer catalyst, stirring at room is reacted 1 h; Add 4.5 mmol arylamine to the flask the inside at last, stirring at room is reacted 1 h, has just obtained target compound.After having reacted, at first on Rotary Evaporators, steam solvent acetone (recycling), in flask, add about 50 ml of mixture of ice and water again, after fully stirring, suction filtration, oven dry, recrystallization obtains corresponding N-phenyl- N'The pure product of-(2-acetoxy benzoyl) thiourea derivative.Characterization data is as follows:
EtOH-DMF mixed solvent recrystallization, thread light yellow crystal, productive rate: 91.5%; M.p. 163 ~ 165 ℃; 1H NMR, (CDCl 3, 400 MHz) δ: 10.032 (s, 1H, CONH), 12.974 (s, 1H, CSNH), 8.304 ~ 7.265 (m, 8H, ArH), 2.555 ~ 2.530 (m, 3H, CH 3); 13C NMR (CDCl 3, 100 MHz) δ: 21.253,123.091,123.518,123.960,124.600,126.932,131.535,134.865,143.157,145.123,148.400,164.511,168.062,177.863; IR (KBr, cm -1) ν: 3376.72 (NH), 1772.58 (OC=OCH 3), 1670.58 (NHC=OAr), 1284.95 (C=S); Anal.Calcd. for C 16H 13N 3O 5S (%): C, 53.48; H, 3.65; N, 11.69; Found (%): C, 53.44; H, 3.61; N, 11.72.
N-phenyl- N'The Anion Recognition performance study experiment of-(2-acetoxy benzoyl) thiourea derivative is as follows:
Experiment one: the acceptor that pipettes 0.5 mL respectively N-phenyl- N'The DMSO solution (2 * 10 of-(2-acetoxy benzoyl) thiourea derivative -4MolL -1) in a series of 10 mL color comparison tubes, add 0.5 mL F respectively -, Cl -, Br -, I -, Ac -, H 2PO 4 -, HSO 4 -And ClO 4 -DMSO solution (0.01 molL of anionic 4-butyl ammonium -1), being diluted to 5 ml with DMSO, this moment, acceptor density was 2 * 10 -5MolL -1, anion concentration is 0.001 molL -1, promptly anion concentration is 50 times of acceptor density.Leave standstill after mixing, observe each acceptor anionic response.
Experimental result: add F -, Ac -And H 2PO 4 -The time solution colour by the colourless glassy yellow that becomes, and solution colour is constant when adding other ion.Therefore, N-phenyl- N'-(2-acetoxy benzoyl) thiourea derivative in DMSO solution to F -, Ac -And H 2PO 4 -Therefore the selective colorimetric recognition capability of ion can be used as acceptor and is used for bore hole identification F -, Ac -And H 2PO 4 -Ion.
Experimental results demonstrate, when the concentration of acceptor molecule in DMSO solution is 2.0 * 10 -3~ 2 * 10 -5MolL -1The time, F -, Ac -And H 2PO 4 -Adding can both make acceptor molecule solution by the colourless yellow that becomes, thereby reach open hole detection F -, Ac -And H 2PO 4 -Effect (negative ion F -, Ac -And H 2PO 4 -Concentration in DMSO is 0. 1 ~ 0.001 molL -1).
Experiment two: the acceptor that pipettes 0.5 mL respectively N-phenyl- N'The DMSO solution (2 * 10 of-(2-acetoxy benzoyl) thiourea derivative -4MolL -1) in a series of 10 mL color comparison tubes, add a little solvent DMSO respectively, add distilled water more respectively, formation contains H 2The O percent by volume is respectively four groups of DMSO/H of 5%, 10%, 20% and 30% 2The O mixed solvent; In every group of color comparison tube, add 0.5 mL F then respectively -, Cl -, Br -, I -, Ac -, H 2PO 4 -, HSO 4 -And ClO 4 -DMSO solution (0.01 molL of anionic 4-butyl ammonium -1), being diluted to 5 ml with DMSO at last, this moment, acceptor density was 2 * 10 -5MolL -1, anion concentration is 0.001 molL -1, promptly anion concentration is 50 times of acceptor density.Leave standstill after mixing, observe each acceptor anionic response.
Experimental result: in BVF is 5%, 10%, 15% mixed solvent, add F -, Ac -And H 2PO 4 -The time solution colour by colourless yellowing.Be increased to 20% and work as water cut, have only adding Ac -The time solution by the colourless yellow that becomes, realized the effect of bore hole identification this moment.And along with the increase of water cut, the difference of discovery water cut can effectively be regulated and control the selectivity and the sensitivity of identification, thereby realizes in the water-bearing media Ac -Single-minded selectivity detect.
Below by acceptor N-phenyl- N'Ultraviolet-visible (UV-vis) spectrum of-(2-acetoxy benzoyl) thiourea derivative and negative ion effect, ultraviolet titration experiments are to its identification F -, Ac -And H 2PO 4 -Mechanism analyze and research.
Ultraviolet-visible (UV-vis) spectrum: in pure DMSO, survey respectively acceptor and with the UV-vis spectrum (Fig. 1) of the mixed solution of different anions.In UV-vis spectrum, acceptor has maximum absorption band at 338 nm places, adds F in acceptor respectively -, Cl -, Br -, I -, Ac -, H 2PO 4 -, HSO 4 -And ClO 4 -During anionic TBuA salt solusion, has only F -, Ac -And H 2PO 4 -The adding of ion makes acceptor significantly reduce at the absorption peak at 338 nm places, occurs new strong absorption peak simultaneously at 408 nm places, and other negative ion does not have obvious influence to the absorption peak of acceptor.When the water cut in the system increases to 20%,, thereby above-mentioned three kinds of alkali anions are distinguished an acceptor molecule selectivity identification Ac owing to intensive polar solvent water will be competed in conjunction with negative ion -, and solution is by the colourless yellow that becomes.That is to say that be subjected to physical efficiency to Ac this moment -Realize selectivity bore hole identification (Fig. 2).
Ultraviolet titration: the DMSO solution (2 * 10 that pipettes 2 mL acceptors -5MolL -1) in quartz colorimetric utensil, add Ac gradually with accumulation application of sample method -DMSO solution (0.01 molL of 4-butyl ammonium -1), in 25 ℃ of ultra-violet absorption spectrum (pure DMSO makes reference) (see figure 3)s of following the trail of system in the titration process.Absorption spectromtry shows: in the ultraviolet titration process along with Ac -Continuous adding because acceptor molecule is subjected to its absorption peak at 338 nm places of anionic perturbation and reduces gradually, the while new absorption peak occurred at 395 nm places, and peak value increases gradually.And an isobestic point clearly appears at 353 nm places, this mainly is because at first destroyed intramolecular hydrogen bond after adding negative ion, has meanwhile formed stable hydrogen bond complex between host-guest again.Experiment showed, at F -And H 2PO 4 -Exist down and also can find and top similar phenomena.Measure acceptor and Ac by mol ratio (Job-Plot) method -Absorbance is to [Ac when 409 nm -]/[Ac -+ acceptor] the working curve (see figure 4).As seen from the figure, as [Ac -]/[Ac -+ acceptor] be 0.5 o'clock, it is maximum that absorbance reaches, and acceptor and Ac are described -Formed stable 1:1 type super molecular complex.397 nm place absorbances are related with anion concentration, calculate acceptor molecule and F through the least square curve fit program -, Ac -And H 2PO 4 -Complexation constant be respectively 8.9 * 10 3MolL -1, 1.6 * 10 4MolL -1With 4.7 * 10 3MolL -1, show that acceptor molecule is followed successively by strong and weak variation of anionic mating capability: Ac -F -H 2PO 4 -Cl -~ Br -~ I -~ HSO 4 -, this variation tendency and the strong and weak sequence consensus of anionic alkalescence.
1H NMR titration experiments: with DMSO- d 6Be solvent, be Ac -The nuclear-magnetism titration of ion pair acceptor.Prepare 0.5 mL10 mmolL -1The DMSO-of acceptor molecule d 6Solution places the nuclear-magnetism pipe, and the proton nmr spectra of at first doing is then to the DMSO-that wherein drips the tetrabutylammonium acetate ammonium with microsyringe d 6Solution adopts the accumulation sampling system, makes the object anion concentration be added drop-wise to 2.5 times one by one from 0.1 times of main body, does the hydrogen spectrum after every dropping once fully shakes up one time.Because the formation of intramolecular hydrogen bond causes the result of the effect of deshielding, cause H among the NH of acceptor molecule aAnd H bThe proton peak displacement all appear at low, be respectively δ 11.878, δ 12.601, and, p-NO 2Appearance, make H bChemical shift appear at minimum.Ac in system -Concentration hour (0 → 0.5 times), H aProton peak move H to low bProton peak slightly move to High-Field, the proton peak peak shape all broadens, integral area reduces, and shows Ac -And acceptor molecule forms complex between Subjective and Objective by the intermolecular ydrogen bonding effect.As the Ac that joins 0.5 times -The time, two new peaks appear at δ 10.975 and δ 10.562 places, and this is because behind the hydrogen bond rupture in intramolecular hydrogen bond and its part and Ac -The result of the two coexistence of intermolecular ydrogen bonding that forms, its possible one-tenth key pattern is as shown below:
Work as Ac -When being added drop-wise to 1.5 times, H aAnd H bProton peak obviously disappear.Because the proton peak that intermolecular ydrogen bonding forms begins to move to low, and gradually step-down, broaden, this also proves main body and Ac once more -Be that mode with hydrogen bond combines.Simultaneously and since negative ion with promoted that electric charge moves in the acceptor molecule after acceptor molecule combines, make electric density increase on the phenyl ring, so the chemical shift of fragrant proton peak is moved (see figure 5) to High-Field on the phenyl ring.
In sum, N-phenyl- N'-(2-acetoxy benzoyl) thiourea derivative is at pure DMSO, DMSO/H 2O(V:V=8:2) in the solution, can be to F -, Ac -And H 2PO 4 -Selectivity bore hole recognition effect is preferably arranged.When add these three kinds of negative ion in its DMSO solution after, solution colour is by the colourless glassy yellow that becomes.By research DMSO/H 2Acceptor molecule and anionic effect in the O mixed solution find can effectively regulate and control by the difference of water cut the selectivity and the sensitivity of identification, thereby realize in the water-bearing media Ac -Single-minded selectivity detect.By UV-vis spectrum and 1H NMR titration experiments has been inquired into possible recognition mechanism, proves the essence that has formed hydrogen bond between negative ion and acceptor molecule.Realized Ac to increase polarity of solvent by in system, introducing water -The identification of single-minded selectivity, and can form stable 1:1 type complex. 1H NMR titration experiments has further confirmed acceptor molecule and anionic hydrogen bond action essence.
Description of drawings
Fig. 1 is the UV-vis spectrogram of acceptor when pure DMSO and the interaction of each negative ion
Fig. 2 is that acceptor is in 20% Aquo System solution (2 * 10 -5MolL -1) UV-vis spectrogram when interacting with each negative ion
Fig. 3 is Ac -Acceptor molecule (2 * 10 when existing -5MolL -1) abosrption spectrogram in DMSO
Fig. 4 is acceptor and Ac -Combination Job figure
Fig. 5 is DMSO-d 6Middle acceptor molecule is at Ac -When existing 1H NMR spectrogram
Embodiment
Below by concrete enforcement to acceptor molecule of the present invention to F -, Ac -And H 2PO 4 -The selectivity detection method be further described.
Embodiment 1
Pipette the acceptor of 0.5 mL respectively N-phenyl- N'The DMSO solution (2 * 10 of-(2-acetoxy benzoyl) thiourea derivative -4MolL -1) in a series of 10 mL color comparison tubes.Add 0.5 mL F respectively -, Cl -, Br -, I -, Ac -, H 2PO 4 -, HSO 4 -And ClO 4 -DMSO solution (0.01 molL of anionic 4-butyl ammonium -1), being diluted to 5 ml with DMSO, this moment, acceptor density was 2 * 10 -5MolL -1, anion concentration is 0.001 molL -1, promptly anion concentration is 50 times of acceptor density.Leave standstill after mixing, if solution colour by the colourless glassy yellow that becomes, then adds F -, Ac -Or H 2PO 4 -If solution colour is constant, then be other negative ion.
Embodiment 2
Pipette the acceptor of 0.5 mL respectively N-phenyl- N'The DMSO solution (2 * 10 of-(2-acetoxy benzoyl) thiourea derivative -3MolL -1) in a series of 10 mL color comparison tubes.Add 0.5 mL F respectively -, Cl -, Br -, I -, Ac -, H 2PO 4 -, HSO 4 -And ClO 4 -DMSO solution (0. 1 molL of anionic 4-butyl ammonium -1), being diluted to 5 ml with DMSO, this moment, acceptor density was 2 * 10 -4MolL -1, anion concentration is 0.01 molL -1, promptly anion concentration is 50 times of acceptor density.Leave standstill after mixing, if solution colour by the colourless glassy yellow that becomes, then adds F -, Ac -Or H 2PO 4 -If solution colour is constant, then be other negative ion.
Embodiment 3
Pipette the acceptor of 0.5 mL respectively N-phenyl- N'The DMSO solution (2 * 10 of-(2-acetoxy benzoyl) thiourea derivative -2MolL -1) in a series of 10 mL color comparison tubes.Add 0.5 mL F respectively -, Cl -, Br -, I -, Ac -, H 2PO 4 -, HSO 4 -And ClO 4 -DMSO solution (1 molL of anionic 4-butyl ammonium -1), being diluted to 5 ml with DMSO, this moment, acceptor density was 2 * 10 -3MolL -1, anion concentration is 0.1 molL -1, promptly anion concentration is 50 times of acceptor density.Leave standstill after mixing,, then add F if solution colour becomes faint yellowly by colourless -, Ac -Or H 2PO 4 -If solution colour is constant, then be other negative ion.
Embodiment 4
Pipette the acceptor of 0.5 mL respectively N-phenyl- N'The DMSO solution (2 * 10 of-(2-acetoxy benzoyl) thiourea derivative -4MolL -1) in a series of 10 mL color comparison tubes, add a little solvent DMSO respectively, add 1 mL distilled water more respectively, make V (DMSO): V (H 2O)=8:2; Add 0.5 mL F then successively -, Cl -, Br -, I -, Ac -, H 2PO 4 -, HSO 4 -And ClO 4 -DMSO solution (0.01 molL of anionic 4-butyl ammonium -1), be diluted to 5 ml with DMSO at last, leave standstill after mixing, observe each acceptor to anionic response.If solution colour is by colourless yellowing, that then add is Ac -Ion; If solution colour is constant, then be other negative ion.
Embodiment 5
Pipette the acceptor of 0.5 mL respectively N-phenyl- N'The DMSO solution (2 * 10 of-(2-acetoxy benzoyl) thiourea derivative -4MolL -1) in a series of 10 mL color comparison tubes, add a little solvent DMSO respectively, add 0.5 mL distilled water more respectively, make V (DMSO): V (H 2O)=9:1; Add 0.5 mL F then successively -, Cl -, Br -, I -, Ac -, H 2PO 4 -, HSO 4 -And ClO 4 -DMSO solution (0.01 molL of anionic 4-butyl ammonium -1), be diluted to 5 ml with DMSO at last, leave standstill after mixing, observe each acceptor to anionic response.If solution colour is by colourless yellowing, that then add is F -, Ac -Or H 2PO 4 -If solution colour is constant, then be other negative ion.
Embodiment 6
Pipette the acceptor of 0.5 mL respectively N-phenyl- N'The DMSO solution (2 * 10 of-(2-acetoxy benzoyl) thiourea derivative -4MolL -1) in a series of 10 mL color comparison tubes, add a little solvent DMSO respectively, add 0.25 mL distilled water more respectively, make V (DMSO): V (H 2O)=9.5:0.5; Add 0.5 mL F then successively -, Cl -, Br -, I -, Ac -, H 2PO 4 -, HSO 4 -And ClO 4 -DMSO solution (0.01 molL of anionic 4-butyl ammonium -1), be diluted to 5 ml with DMSO at last, leave standstill after mixing, observe each acceptor to anionic response.If solution colour is by colourless yellowing, that then add is F -, Ac -Or H 2PO 4 -If solution colour is constant, then be other negative ion.

Claims (4)

1. negative ion F -, Ac -And H 2PO 4 -The bore hole recognition methods, it is characterized in that: with N-phenyl- N '-(2-acetoxy benzoyl) thiourea derivative is an acceptor molecule, in the DMSO of acceptor molecule or DMSO/H 2In the O solution, F -, Ac -And H 2PO 4 -Adding can make the solution of acceptor molecule by the colourless yellow that becomes; Described DMSO/H 2In the O solution, H 2The percent by volume of O is 5% ~ 15%.
2. negative ion F as described in requiring 1 as power -, Ac -And H 2PO 4 -The bore hole recognition methods, it is characterized in that: described acceptor molecule is in DMSO or DMSO/H 2Concentration in the O solution is 2.0 * 10 -3~ 2.0 * 10 -5MolL -1
3. negative ion F as described in requiring 1 as power -, Ac -And H 2PO 4 -The bore hole recognition methods, it is characterized in that: negative ion F -, Ac -And H 2PO 4 -At DMSO or DMSO/H 2Concentration in the O solution is 0.1 ~ 0.001 molL -1
4. negative ion F as described in requiring 1 as power -, Ac -And H 2PO 4 -The bore hole recognition methods, it is characterized in that: at DMSO/H 2In the O solution, work as H 2The percent by volume of O is 20% o'clock, Ac -Adding can make solution by the colourless yellow that becomes.
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