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3,4-Pyridinedicarboxylic acid is a colorless to slightly yellow solid, commonly in the form of crystals or powders. Its CAS number is 490-11-9, with the molecular formula C7H5NO4. It has a certain solubility in water and can form a solution with water. It can also be dissolved in some organic solvents. The crystal structure belongs to the monoclinic system. Its lattice parameters can be determined by methods such as X-ray diffraction. Having two carboxyl groups, it can self dissociate to produce hydrogen ions and regulate pH in solution. The optical properties are related to their structure. It has an absorption band in the ultraviolet spectral region and can be characterized based on the absorption spectrum. The thermal properties can be characterized by techniques such as thermogravimetric analysis (TGA). During the heating process, it may undergo decomposition, dehydration, or other reactions. Some common uses in metal complexing agents, but these applications demonstrate their importance in catalysis, fluorescent probes, electrochemical materials, and metal coordination polymers.
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Chemical Formula |
C7H5NO4 |
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Exact Mass |
167 |
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Molecular Weight |
167 |
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m/z |
167 (100.0%), 168 (7.6%) |
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Elemental Analysis |
C, 50.31; H, 3.02; N, 8.38; O, 38.29 |
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3,4-Pyridinedicarboxylic acid, as a copper ion determination reagent, has a wide range of applications in chemical analysis, environmental monitoring, materials science, biomedical and other fields.
1. In the field of chemical analysis
In the field of chemical analysis, it is widely used for quantitative determination of copper ions due to its ability to form stable complexes with copper ions. This measurement method has the advantages of easy operation, high sensitivity, and good selectivity, and is one of the commonly used methods in chemical analysis.
(1) Quantitative analysis:
By measuring the color intensity (such as absorbance) of the complex formed between the substance and copper ions, quantitative analysis of copper ions can be achieved. This method is applicable to various copper containing samples, including aqueous solutions, solid samples, and biological samples.
(2) Reaction kinetics research:
The study of complexation reaction kinetics with copper ions is also an important direction in the field of chemical analysis. By studying parameters such as reaction rate and reaction mechanism, we can gain a deeper understanding of the intrinsic laws of complexation reactions and provide theoretical basis for optimizing measurement methods.
2. Environmental monitoring field
In the field of environmental monitoring, the content of copper ions is one of the important indicators for evaluating the degree of pollution of environmental media such as water and soil. As a copper ion determination reagent, it has the following uses in environmental monitoring:
(1) Water monitoring:
By using it to measure the copper ion content in water bodies, the degree of water pollution can be evaluated, providing scientific basis for the protection and management of water resources. At the same time, this method can also be used to monitor the copper ion content in industrial wastewater, domestic sewage and other discharge sources to prevent environmental pollution.
(2) Soil monitoring:
The copper ion content in soil is also an important indicator for evaluating the degree of soil pollution. By measuring the copper ion content in soil, the pollution status of the soil can be understood, providing data support for soil remediation and treatment. As a copper ion determination reagent, it also has broad application prospects in soil monitoring.
3. Materials Science Field
In the field of materials science, copper ions play an important role in the corrosion of metal materials, the preparation of catalysts, and the synthesis of new materials. As a copper ion determination reagent, it has the following uses in materials science:
(1) Corrosion research:
By measuring the copper ion content on the surface of metal materials or in solutions, the degree of corrosion of materials can be evaluated, providing data support for the anti-corrosion treatment of materials. As a copper ion determination reagent, it has important application value in corrosion research.
(2) Catalyst preparation:
Copper ions are often used as active components or additives in the preparation process of catalysts. By measuring the copper ion content in the catalyst, the composition and performance of the catalyst can be understood, providing guidance for the optimization and modification of the catalyst. As a copper ion determination reagent, it also has broad application prospects in the field of catalyst preparation.
4. Biomedical field
In the biomedical field, copper ions play important physiological functions in organisms, such as participating in enzyme catalytic reactions and maintaining normal nervous system function. However, excessive copper ions can also cause damage to living organisms. Therefore, measuring the copper ion content in biological samples is of great significance for evaluating the health status and disease diagnosis of organisms. As a copper ion determination reagent, it has the following uses in the biomedical field:
(1) Blood testing:
By measuring the copper ion content in the blood, the copper metabolism status of the human body can be evaluated, providing data support for the diagnosis and treatment of copper metabolism disorders.
(2) Organizational sample analysis:
In biomedical research, it is often necessary to analyze the copper ion content in tissue samples to understand their distribution and metabolism in the organism. As a copper ion determination reagent, it can be used for the determination of copper ion content in tissue samples, providing important data support for biomedical research.
Research field of supramolecular chemistry
The two carboxyl groups in 3,4-PDCA molecule contain oxygen atoms, and the nitrogen atom on the pyridine ring also has lone pair electrons, which can act as electron donors to form coordination bonds with metal ions. By selecting appropriate metal ions, metal organic supramolecular systems with specific structures and functions can be constructed. In this study, BaCl ₂ · 2H ₂ O and ligand 3,4-pyridinedioic acid reacted under solvothermal conditions to form the complex [Ba ₂ (pdc) ₂ (H ₂ O) ∝] ₙ (H ₂ pdc=3,4-pyridinedioic acid). The generated crystals were characterized by single crystal X-ray, elemental analysis, and FT-IR. The results showed that Ba ¹ and Ba ² adopted the geometric configurations of an eight coordinate twisted square antiprism and a ten coordinate double capped square prism, respectively. The entire pdc ² ⁻ served as a four toothed bridging ligand connecting four different Ba (II) atoms to form a two-dimensional network structure, and O-H... N hydrogen bonds bound the two-dimensional network together to form a three-dimensional structure. This metal organic supramolecular system not only has a unique structure, but also exhibits good fluorescence and thermal stability, which may have potential application value in fields such as fluorescent materials and optical materials.
Participate in the supramolecular self-assembly process
Supramolecular self-assembly refers to the process in which molecules spontaneously form ordered structures through non covalent interactions. The carboxyl and pyridine rings in 3,4-PDCA molecules can self assemble with other molecules through non covalent interactions such as hydrogen bonding and π - π interactions. For example, carboxyl groups can form hydrogen bonds, and pyridine rings can undergo π - π stacking interactions, which together drive the self-assembly of molecules into supramolecular aggregates with specific structures and functions. These supramolecular structures have significant potential for applications in nanomaterials, drug controlled release, sensors, and other fields. For example, the nanowires formed by self-assembly can be used as the building blocks of nano electronic devices, nanotubes can be used for drug delivery and molecular separation, and gel can be used as smart materials for drug controlled release systems. The process of supramolecular self-assembly is spontaneous and reversible, and can be regulated by simple solution treatment or external stimuli such as temperature, pH, light, etc. to control the properties of the self-assembly process and supramolecular structure. The supramolecular self-assembly involving 3,4-PDCA provides a simple and effective method for preparing novel functional materials.
The specific synthesis method of 3,4-Pyridinedicarboxylic acid:
(1) Put 750 g (5.55 mol) of concentrated sulfuric acid and 1.4 g (0.175 mol) of selenium powder into a four-neck flask and heat it. The flask is equipped with a stirrer, a thermometer, a dropping cylinder and a large gas outlet tube. Once the temperature reaches 275 degrees Celsius, the selenium is dissolved in concentrated sulfuric acid.
Dissolve 1 g (0.125 mol) of selenium powder in 50 g (0.37 mol) of sulfuric acid, heat briefly to 275°C, and dissolve it in 550 g (4.08 mol) of isoquinoline solution with 129.2 g (1 mol) after cooling to room temperature Combine with sulfuric acid, drip into sulfuric acid with a dropper, keep the temperature of the reaction process at 270-280°C.
During implementation, water vapor and sulfur dioxide pass through the gas discharge pipe and are extracted using a water jet pump through a funnel placed above.
After about 2 l/2 hours, the whole solution was added dropwise and the temperature was maintained between 270 - 280°C for a further hour. After cooling the mixture to room temperature, add 400ml of water, add 5g of activated charcoal and cook for a few minutes.
Selenium and activated carbon were filtered off, and the cooled orange-yellow solution was carefully adjusted to pH 1.5 with concentrated ammonia.
(2) A 1-liter four necked flask equipped with a dropper funnel, mechanical stirrer, thermometer, cloth funnel with sandpaper, and water jet pump to induce gas inhalation.
Place 1.68 g of black selenium in 46 mL of concentrated solution and heat. H2SO4, A nearly transparent yellow solution. Then, under vigorous stirring and cooling, 218 g of isoquinoline (1.68 mol) was added dropwise to 925 g of conc in a conical flask. Sulfuric acid (503 mL).
Combine the two solutions prepared in this way together. Subsequently, 2.35 g of black selenium was dissolved in 1260 g concentration in the aforementioned reaction vessel, and H2SO4 was stirred at 270 ° C. After the appearance of a clear yellow solution, heat up to 280 ° C and add sulfuric acid isoquinoline solution dropwise within 2.5 hours. The volume of liquid in the flask remains basically unchanged, and the internal temperature should not be lower than 265 ° C (for local storage).
After addition, stir at 270-280 ° C for 1.25 hours to reduce the solvent volume to around 500mL, then cool the mixture to room temperature and stir the brown syrup like liquid in 660mL of HO.
Add 10 grams of activated carbon to the obtained solution and heat to 80 ° C. After extracting the activated carbon, add concentrated ammonia to the clear solution, adjust the pH to 1.5-2, store in the refrigerator for 10 hours, filter the light brown crystals, suspend them in 500mL of cold distilled water, and filter again.
Dry the obtained acid in a convection oven at 110 degrees Celsius. Finally, 3,4-pyridinedicarboxylic acid was obtained. Production: 210 grams (75% of theory). Recrystallization: Water. The melting point is 250-257 degrees.
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