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2,2′-Bipyridine is an important organic compound widely used in coordination chemistry, catalysis, and material science. It is a bidentate ligand known for forming stable complexes with transition metals. Due to its versatile applications in various scientific fields, understanding its structure, properties, and uses is crucial for researchers and chemists.
This guide provides a comprehensive overview of 2,2′-bipyridine, including its structural characteristics, role as a chelating ligand, applications in industry and research, and potential hazards. Additionally, we will explore its market trends, comparative analysis with similar ligands, and frequently asked questions.
A bipyridine is an organic compound consisting of two pyridine rings connected by a single bond. Pyridine itself is a six-membered nitrogen-containing aromatic ring, and when two such rings are linked, they form a bipyridine structure.
There are several isomers of bipyridine, depending on the position of the bond between the two pyridine rings. The most common isomers include:
2,2′-Bipyridine (2,2′-bipy)
3,3′-Bipyridine
4,4′-Bipyridine
Among these, 2,2′-bipyridine is the most widely studied and utilized due to its excellent ability to coordinate with metal ions, making it a crucial ligand in coordination chemistry.
Yes, bipyridine, particularly 2,2′-bipyridine, is a chelating ligand. A chelating ligand is a molecule that can form multiple bonds with a single metal ion, creating a stable complex.
In the case of 2,2′-bipyridine, the two nitrogen atoms in the pyridine rings can simultaneously coordinate to a metal center, forming a five-membered chelate ring. The ability of 2,2′-bipyridine to chelate enhances the stability of metal-ligand complexes, making it a valuable ligand in fields such as:
Catalysis – Used in metal-catalyzed reactions.
Photochemistry – Forms luminescent metal complexes.
Electrochemistry – Used in redox-active metal complexes.
2,2′-Bipyridine (C₁₀H₈N₂) is a heterocyclic organic compound composed of two pyridine rings linked at the 2-position. It is a colorless to yellow crystalline solid that is sparingly soluble in water but readily soluble in organic solvents such as ethanol and acetone.
This compound is extensively used in coordination chemistry due to its bidentate ligand properties, meaning it can attach to metal centers at two points. The chelating ability of 2,2′-bipyridine makes it an essential ligand in transition metal chemistry.
| Property | Value |
|---|---|
| Molecular Formula | C₁₀H₈N₂ |
| Molecular Weight | 156.18 g/mol |
| Melting Point | 69-72°C |
| Boiling Point | 273°C |
| Solubility | Soluble in organic solvents, slightly soluble in water |
| Appearance | Yellowish crystalline solid |
The structure of 2,2′-bipyridine consists of two pyridine rings connected at the 2-position. The presence of nitrogen atoms in both rings allows the compound to coordinate with metal ions efficiently.
Planar geometry – The molecule tends to adopt a near-planar conformation when complexed with metal ions.
Electron delocalization – The nitrogen lone pairs contribute to the electronic properties of the ligand.
Chelating effect – The two nitrogen atoms form a stable five-membered ring upon coordination with metal ions.
| Isomer | Structure | Chelating Ability | Common Applications |
|---|---|---|---|
| 2,2′-Bipyridine | Nitrogen at 2-position | Strong | Catalysis, photochemistry, coordination chemistry |
| 3,3′-Bipyridine | Nitrogen at 3-position | Weak | Less common in metal complexes |
| 4,4′-Bipyridine | Nitrogen at 4-position | Weak | Precursor for polymer materials |
Due to its strong chelating effect, 2,2′-bipyridine is the most widely used among the bipyridine isomers.
Used as a ligand in transition metal-catalyzed reactions.
Forms stable complexes with metals such as iron, ruthenium, and copper.
Common in oxidation and reduction reactions.
Forms luminescent metal complexes, such as [Ru(bipy)₃]²⁺, used in dye-sensitized solar cells.
Plays a role in light-harvesting applications.
Used in redox-active metal complexes for electronic applications.
Employed in batteries and sensors.
Incorporated into polymers for advanced materials.
Used in molecular electronics.
Acts as a reagent in metal ion detection.
Helps in spectrophotometric analysis.
While 2,2′-bipyridine is widely used in research and industry, it poses certain hazards that should be considered.
Can cause skin and eye irritation upon contact.
Inhalation may lead to respiratory tract irritation.
Prolonged exposure may be toxic to organs.
Not highly biodegradable, leading to potential environmental persistence.
Can be toxic to aquatic life in high concentrations.
Use gloves and protective eyewear when handling.
Work in a well-ventilated area.
Dispose of waste according to hazardous chemical regulations.
2,2′-bipyridine is a crucial compound in coordination chemistry, catalysis, and material science. Its ability to form stable metal complexes makes it an essential ligand in numerous applications, from photochemistry to electrochemistry. However, handling precautions must be taken due to its potential health and environmental hazards.
With ongoing research in organic electronics, catalysis, and sustainable chemistry, the demand for 2,2′-bipyridine is expected to grow. Understanding its properties, applications, and risks will help scientists and industrial professionals use it effectively and safely.
1. Is 2,2′-bipyridine soluble in water?
It is sparingly soluble in water, but dissolves well in organic solvents such as ethanol and acetone.
2. What metals does 2,2′-bipyridine commonly complex with?
It forms strong complexes with iron, ruthenium, copper, cobalt, and platinum.
3. What is a common application of 2,2′-bipyridine in catalysis?
It is widely used in transition metal-catalyzed oxidation and reduction reactions.
4. Can 2,2′-bipyridine be used in organic electronics?
Yes, it is used in molecular electronics and conductive polymers.
5. Is 2,2′-bipyridine hazardous?
Yes, it can cause skin, eye, and respiratory irritation and should be handled with care.
