CN113029982A - Method for measuring complexation stoichiometric ratio of polyphenol compound and metal ion by spectrophotometry - Google Patents
Method for measuring complexation stoichiometric ratio of polyphenol compound and metal ion by spectrophotometry Download PDFInfo
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- 229910021645 metal ion Inorganic materials 0.000 title claims abstract description 55
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 19
- -1 polyphenol compound Chemical class 0.000 title claims abstract description 17
- 238000002798 spectrophotometry method Methods 0.000 title claims abstract description 7
- 238000010668 complexation reaction Methods 0.000 title claims description 27
- 239000000243 solution Substances 0.000 claims abstract description 62
- 238000004088 simulation Methods 0.000 claims abstract description 28
- 238000002835 absorbance Methods 0.000 claims abstract description 24
- 150000008442 polyphenolic compounds Chemical class 0.000 claims abstract description 24
- 239000011535 reaction buffer Substances 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 238000005259 measurement Methods 0.000 claims abstract description 7
- 239000007983 Tris buffer Substances 0.000 claims description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229940125717 barbiturate Drugs 0.000 claims description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims 1
- QJYNZEYHSMRWBK-NIKIMHBISA-N 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose Chemical compound OC1=C(O)C(O)=CC(C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 QJYNZEYHSMRWBK-NIKIMHBISA-N 0.000 description 17
- 238000000746 purification Methods 0.000 description 13
- 240000006394 Sorghum bicolor Species 0.000 description 8
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 8
- 235000018553 tannin Nutrition 0.000 description 8
- 229920001864 tannin Polymers 0.000 description 8
- 239000001648 tannin Substances 0.000 description 8
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 7
- 244000269722 Thea sinensis Species 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000008351 acetate buffer Substances 0.000 description 3
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 3
- 235000005487 catechin Nutrition 0.000 description 3
- 229950001002 cianidanol Drugs 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- G01—MEASURING; TESTING
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
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- G—PHYSICS
- G16—INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR SPECIFIC APPLICATION FIELDS
- G16C—COMPUTATIONAL CHEMISTRY; CHEMOINFORMATICS; COMPUTATIONAL MATERIALS SCIENCE
- G16C20/00—Chemoinformatics, i.e. ICT specially adapted for the handling of physicochemical or structural data of chemical particles, elements, compounds or mixtures
- G16C20/10—Analysis or design of chemical reactions, syntheses or processes
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Abstract
A method for measuring the stoichiometric ratio of the complex reaction between polyphenol compound and metal ion by spectrophotometry. The method comprises the following steps: (1) respectively preparing polyphenol solution, metal ion solution and reaction buffer solution with equal molar concentration; (2) respectively adding 0-20 muL of metal ion solution and 20-0 muL of polyphenol solution into a 1mL cuvette to keep the total volume of the metal ion solution and the polyphenol solution added each time to be 20 muL, then adding reaction buffer solution to 1mL, fully mixing, and standing for 1-2 min; (3) after each mixing, measuring the absorbance value of the reaction solution at 330nm by using a spectrophotometer; (4) and collecting the absorbance value of each measurement, and performing four-item curve simulation by using MatLab software to obtain an X value corresponding to the highest point of the curve, namely the stoichiometric ratio of the complex. The method has the advantages of simple and convenient technical operation, low requirements on instruments and equipment and good stability.
Description
Technical Field
The invention relates to a method for measuring the stoichiometric ratio of complex reaction of polyphenol compounds and metal ions by using a spectrophotometry, belonging to the technical field of chemical analysis.
Background
Complexing precipitated metal ions is one of the important properties of polyphenolic compounds. Many metal ions have important physiological roles in the organism, and polyphenol compounds affect their biological activities by forming structurally close complexes with these metal ions. The ability of the polyphenol compound to complex metal ions is derived from catechol and galloyl structures in the polyphenol compound.
In the presence of metal ions, phenolic hydroxyl groups are first deprotonated and then undergo a complexing reaction with the metal ions in the form of covalent bonds to form polyphenol-metal ion complexes.
The technology of the invention utilizes an equimolar continuous variation method to determine the stoichiometric ratio of the complex of the polyphenol-metal ion complex reaction. In a series of solutions prepared by the method, the metal ion concentration [ M ] and the ligand concentration [ L ] are simultaneously changed, but the sum (C) of the metal ion concentration [ M ] and the ligand concentration [ L ] is not changed, namely: [ M ] + [ L ] ═ C (where [ L ] ═ CX, [ M ] ═ C (1-X), X ═ L ]/C, X is the mole fraction, and C is a constant, i.e., the sum of the concentrations of the two). The concentration of the polyphenol compound ligand and the metal ions in the mixture is changed (the total concentration of the polyphenol compound ligand and the metal ions in the mixture is kept unchanged), and the ultraviolet absorbance value of the mixed solution is changed. The mixture has a maximum absorbance value at the characteristic absorption wavelength when the molar concentration of ligand to metal ion in the mixture reaches the stoichiometric ratio for the complex.
Disclosure of Invention
The invention aims to provide a method for measuring the stoichiometric ratio of the complexation reaction of a polyphenol compound and metal ions by using a spectrophotometry.
The technical scheme of the invention is as follows: a method for measuring the stoichiometric ratio of the complex reaction of polyphenol compounds and metal ions by using a spectrophotometry method is specifically prepared by the following steps:
(1) respectively preparing 1-10mM of polyphenol solution with equimolar concentration, metal ion solution and reaction buffer solution;
(2) respectively adding 0, 2, 4,6, … … and 20 mu L of metal ion solution and 20, 18, 16, 14, … … and 0 mu L of polyphenol solution into a 1mL cuvette for each time, keeping the total volume of the metal ion solution and the polyphenol solution added for each time unchanged at 20 mu L, then adding reaction buffer solution to 1mL, fully mixing, and standing at room temperature for 1-2 min;
(3) after each mixing, measuring the absorbance value of the reaction solution at 330nm by using a spectrophotometer, and taking the reaction buffer solution as a blank;
(4) and collecting the absorbance value of each measurement, and performing four-term curve simulation by using MatLab software to obtain a four-term simulation curve graph with [ M ]/[ M + PP ] ([ M ] ═ molar concentration of metal ions, [ M + PP ] ═ total molar concentration of metal ions and polyphenol compounds) as an abscissa and the absorbance value as an ordinate, wherein the X value corresponding to the highest point of the curve is the stoichiometric ratio of the complex.
The reaction buffer solution in the step (1) is phosphate, citrate, carbonate, acetate, barbiturate, Tris (Tris (hydroxymethyl aminomethane) and other buffer solutions.
The MatLab software in the step (4) carries out a four-term curve simulation equation as follows:
wherein: k is a series number, alpha is a numerical value of a point where a curve intersects with a y axis, y is an absorbance value of the mixed solution, x is a molar ratio of the metal ion concentration to the total concentration, and the total concentration is the metal ion concentration plus the polyphenol compound concentration.
The invention has the beneficial effects that: the method has the advantages of simple and convenient technical operation, low requirements on instruments and equipment and good stability, and can be used for measuring the stoichiometric ratio of the complex reaction of the polyphenol compound and the metal ions.
Drawings
FIG. 1 tea polyphenols (Cat) and Al respectively3+Complexation reaction at pH6.0The curve should be simulated in terms of stoichiometry.
FIG. 2 tea polyphenols (Cat) and Fe separately3+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 3 tea polyphenols (Cat) and Sn2+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 4 sorghum tannin Purification (PC) with Al, respectively3+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 5 sorghum tannin Purification (PC) with Cu, respectively2+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 6 sorghum tannin Purification (PC) with Fe respectively3+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 7 sorghum tannin Purification (PC) with Sn, respectively2+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 8 sorghum tannin Purification (PC) with Zn, respectively2+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 91,2,3,4, 6-O-Pentagalloylglucose (PGG) and Cu, respectively2+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 101,2,3,4, 6-O-Pentagalloylglucose (PGG) and Fe, respectively3+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 111,2,3,4, 6-O-PentaGalloylglucose (PGG) and Pb, respectively2+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 121,2,3,4, 6-O-Pentagalloylglucose (PGG) and Sn, respectively2+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 131,2,3,4, 6-O-Pentagalloylglucose (PGG) and Al3+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 6.0.
FIG. 141,2,3,4, 6-O-Pentagalloylglucose (PGG) and Al3+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 4.0.
FIG. 151,2,3,4, 6-O-Pentagalloylglucose (PGG) and Fe, respectively3+A four-way simulation curve of the stoichiometric ratio of the complexation reaction at pH 4.0.
Detailed Description
The present embodiment is only for explaining the invention, and not for limiting the invention, and those skilled in the art can make modifications without inventive contribution to the present embodiment as required after reading the present specification, but all of them are protected by patent law within the scope of the claims of the present invention.
Example 1: tea polyphenols (catechin, Cat) and Al3+、Fe3+、Sn2+Method for measuring stoichiometric ratio of complexation reaction under pH6.0 condition
1mM of catechin (Cat) and metal ions (Al) were prepared separately3+、Fe3+、Sn2+) Solution and reaction buffer solution; respectively adding 0, 2, 4,6, … … and 20 mu L of metal ion solution and 20, 18, 16, 14, … … and 0 mu L of polyphenol solution into a 1mL cuvette at each time, keeping the total volume of the metal ion solution and the polyphenol solution added at each time constant at 20 mu L, then adding 980 mu L of acetate buffer solution with pH of 6.0, and fully mixing; standing at room temperature for 1-2min, taking the reaction buffer as a blank, and measuring the absorbance value of the reaction solution at 330nm by using a spectrophotometer; collecting the absorbance value of each measurement, and performing four-item curve simulation by using MatLab software to obtain [ M ]]/[M+PP]([M]Molar concentration of metal ion, [ M + PP ]]Total molar concentrations of metal ions and polyphenol) are plotted on the abscissa and absorbance values are plotted on the ordinate in a four-way simulation (see fig. 1-3), and the X value corresponding to the highest point of the curve (see table 1) is the stoichiometric ratio of the complex.
TABLE 1 tea polyphenols (Catechin, Cat) with Al, respectively3+、Fe3+、Sn2+Stoichiometric ratio of complexation reaction at pH6.0
| Metal ion | Value of X | Stoichiometric ratio ([ M)]/[M+PP]) |
| Al3+ | 0.30 | 1:2 |
| Fe3+ | 0.33 | 1:2 |
| Sn2+ | 0.30 | 1:2 |
Example 2: sorghum tannin purities (EC)16-C, PC) with Al, respectively3+、Fe3+、Sn2+、Zn2+、Cu2+Method for measuring stoichiometric ratio of complexation reaction under pH6.0 condition
Preparing 1mM sorghum tannin purifyed matter (EC) respectively16-C, PC) and metal ions (Al)3+、Fe3+、Sn2+、Zn2+、Cu2 +) Solution and reaction buffer solution; respectively adding 0, 2, 4,6, … … and 20 mu L of metal ion solution and 20, 18, 16, 14, … … and 0 mu L of polyphenol solution into a 1mL cuvette at each time, keeping the total volume of the metal ion solution and the polyphenol solution added at each time constant at 20 mu L, then adding 980 mu L of acetate buffer solution with pH of 6.0, and fully mixing; standing at room temperature for 1-2min, taking reaction buffer as blank, and performing light splittingThe absorbance value of the reaction solution at 330nm is measured by a photometer; collecting the absorbance value of each measurement, and performing four-item curve simulation by using MatLab software to obtain [ M ]]/[M+PP]The absorbance values are plotted on the abscissa and the ordinate in a four-way simulation (see FIGS. 4 to 8), and the X value (see Table 2) corresponding to the highest point of the curve is the stoichiometric ratio of the complex.
TABLE 2 sorghum tannin purities (EC)16-C, PC) with Al, respectively3+、Fe3+、Sn2+、Zn2+、Cu2+Stoichiometric ratio of complexation reaction at pH6.0
Example 3: 1,2,3,4, 6-O-Pentagalloylglucose (PGG) and Al3+、Fe3+、Sn2+、Zn2+、Cu2+Method for measuring stoichiometric ratio of complexation reaction under pH6.0 condition
1mM of 1,2,3,4, 6-O-Pentagalloylglucose (PGG) and metal ions (Fe) were prepared respectively3+、Pb2+、Zn2 +、Cu2+) Solution and reaction buffer solution; respectively adding 0, 2, 4,6, … … and 20 mu L of metal ion solution and 20, 18, 16, 14, … … and 0 mu L of polyphenol solution into a 1mL cuvette at each time, keeping the total volume of the metal ion solution and the polyphenol solution added at each time constant at 20 mu L, then adding 980 mu L of acetate buffer solution with pH of 6.0, and fully mixing; standing at room temperature for 1-2min, taking the reaction buffer as a blank, and measuring the absorbance value of the reaction solution at 330nm by using a spectrophotometer; collecting the absorbance value of each measurement, and performing four-item curve simulation by using MatLab software to obtain [ M ]]/[M+PP]The absorbance values are plotted on the abscissa and the ordinate in a four-way simulation (see FIGS. 9 to 13), and the X value (see Table 3) corresponding to the highest point of the curve is the stoichiometric ratio of the complex.
TABLE 31,2,3,4, 6-O-Pentagalloylglucose (PGG) with Al, respectively3+、Fe3+、Sn2+、Zn2+、Cu2+Stoichiometric ratio of complexation reaction at pH6.0
| Metal ion | Value of X | Stoichiometric ratio ([ M)]/[M+PP]) |
| Cu2+ | 0.61 | 2:1 |
| Fe3+ | 0.67 | 2:1 |
| Pb2+ | 0.62 | 2:1 |
| Zn2+ | 0.53 | 1:1 |
| Al3+ | 0.67 | 2:1 |
Example 4: 1,2,3,4, 6-O-PentaGalloylglucose (PGG)) Are respectively reacted with Al3+、Fe3+、Sn2+、Zn2+、Cu2+Method for measuring stoichiometric ratio of complexation reaction under pH4.0 condition
1mM of 1,2,3,4, 6-O-Pentagalloylglucose (PGG) and metal ions (Fe) were prepared respectively3+、Cu2+) Solution and reaction buffer solution; respectively adding 0, 2, 4,6, … … and 20 mu L of metal ion solution and 20, 18, 16, 14, … … and 0 mu L of polyphenol solution into a 1mL cuvette at each time, keeping the total volume of the metal ion solution and the polyphenol solution added at each time constant at 20 mu L, then adding 980 mu L of phosphate buffer solution with pH4.0, and fully mixing; standing at room temperature for 1-2min, taking the reaction buffer as a blank, and measuring the absorbance value of the reaction solution at 330nm by using a spectrophotometer; collecting the absorbance value of each measurement, and performing four-item curve simulation by using MatLab software to obtain [ M ]]/[M+PP]The absorbance values are plotted on the abscissa and the ordinate in a four-way simulation (see FIGS. 14 to 15), and the X value corresponding to the highest point of the plot (see Table 4) is the stoichiometric ratio of the complex.
TABLE 41,2,3,4, 6-O-Pentagalloylglucose (PGG) with Al, respectively3+、Fe3+Stoichiometric ratio of complexation reaction at pH4.0
| Metal ion | Value of X | Stoichiometric ratio ([ M)]/[M+PP]) |
| Al3+ | 0.46 | 1:1 |
| Fe3+ | 0.57 | 1:1 |
Claims (4)
1. A method for measuring the stoichiometric ratio of the complexation reaction of a polyphenol compound and metal ions by using a spectrophotometry method is characterized by comprising the following steps of:
(1) respectively preparing 1-10mM of polyphenol solution with equimolar concentration, metal ion solution and reaction buffer solution;
(2) respectively adding 0, 2, 4,6, … … 20 mu L of metal ion solution and 20, 18, 16, 14, … … and 0 mu L of polyphenol solution into a 1mL cuvette at each time, keeping the total volume of the metal ion solution and the polyphenol solution added at each time constant at 20 mu L, then adding reaction buffer solution to 1mL, fully mixing, and standing at room temperature for 1-2 min;
(3) after each mixing, measuring the absorbance value of the reaction solution at 330nm by using a spectrophotometer, and taking the reaction buffer solution as a blank;
(4) and collecting the absorbance value of each measurement, and performing four-term curve simulation by using MatLab software to obtain a four-term simulation curve graph with [ M ]/[ M + PP ] as an abscissa and the absorbance value as an ordinate, wherein the X value corresponding to the highest point of the curve is the stoichiometric ratio of the complex, wherein [ M ] is the molar concentration of the metal ions, and [ M + PP ] is the total molar concentration of the metal ions and the polyphenol compounds.
2. The method according to claim 1, wherein the reaction buffer in step (1) is a buffer such as phosphate, citrate, carbonate, acetate, barbiturate, Tris (Tris).
3. The process according to claim 1, wherein the reaction temperature in step (2) is 0 to 40 ℃.
4. The method of claim 1, wherein the MatLab software in step (4) performs a four-way curve modeling equation y (x) as:
wherein: k is a series number, alpha is a numerical value of a point where a curve intersects with a y axis, y is an absorbance value of the mixed solution, x is a molar ratio of the metal ion concentration to the total concentration, and the total concentration is the metal ion concentration plus the polyphenol compound concentration.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5814521A (en) * | 1995-10-06 | 1998-09-29 | Bayer Corporation | Metal ion determination by sandwich aggregation assay |
| CN106018356A (en) * | 2016-05-04 | 2016-10-12 | 中国林业科学研究院林产化学工业研究所 | Method for testing procyanidine-metal ion complexation capacity through fluorescence quenching method |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5814521A (en) * | 1995-10-06 | 1998-09-29 | Bayer Corporation | Metal ion determination by sandwich aggregation assay |
| CN106018356A (en) * | 2016-05-04 | 2016-10-12 | 中国林业科学研究院林产化学工业研究所 | Method for testing procyanidine-metal ion complexation capacity through fluorescence quenching method |
Non-Patent Citations (4)
| Title |
|---|
| 刘瑜琛等: "分光光度法测定单宁酸-Fe~(3+)反应结合常数及其化学计量比", 《林业工程学报》 * |
| 刘育 等: "《超分子化学 合成受体的分子识别与组装》", 31 December 2001 * |
| 王军等: "钨-3,5二溴水杨基荧光酮-CTMAB-Tween80多元配合物的分光光度法研究", 《光谱学与光谱分析》 * |
| 许晓文 等: "《定量化学分析 第3版》", 30 April 2016 * |
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