4,7-Phenanthroline

4,7-Phenanthroline is a heterocyclic organic compound with the chemical formula C₁₂H₈N₂. It is a derivative of phenanthroline, a nitrogen-containing polycyclic aromatic compound. 4,7-Phenanthroline is of interest in various fields of chemistry and biochemistry due to its ability to act as a ligand in coordination chemistry and its potential applications in analytical chemistry and molecular biology.

Structure and Properties

4,7-Phenanthroline is a planar molecule consisting of three fused benzene rings, with two nitrogen atoms replacing carbon atoms at the 4 and 7 positions of the central ring. This structure imparts unique electronic properties, making it an effective chelating agent.

Molecular Formula: C₁₂H₈N₂

Molar Mass: 180.21 g/mol

Appearance: White to pale yellow crystalline solid

Melting Point: 116-118 °C

Solubility: Soluble in organic solvents such as ethanol, methanol, and acetone; slightly soluble in water.

Synthesis

4,7-Phenanthroline can be synthesized through various methods, including the Skraup synthesis, which involves the cyclization of o-phenylenediamine with glycerol in the presence of an acid catalyst. Another method involves the oxidative coupling of 1,10-phenanthroline with a suitable oxidizing agent.

Applications

Coordination Chemistry

4,7-Phenanthroline is widely used as a ligand in coordination chemistry. It forms stable complexes with a variety of metal ions, including transition metals such as iron, copper, and nickel. These complexes are often used in studies of electron transfer, catalysis, and as models for biological systems.

Analytical Chemistry

In analytical chemistry, 4,7-phenanthroline is used as a reagent for the spectrophotometric determination of metal ions. The formation of colored complexes with metal ions allows for the quantitative analysis of these ions in various samples.

Biological Studies

4,7-Phenanthroline and its metal complexes have been studied for their biological activity, including antimicrobial and anticancer properties. The ability of these complexes to intercalate with DNA and inhibit enzymes makes them potential candidates for therapeutic applications.

Safety and Handling

4,7-Phenanthroline should be handled with care, as it can be harmful if ingested or inhaled. Appropriate personal protective equipment, such as gloves and goggles, should be used when handling this compound.

Also see

• Phenanthroline
• Coordination chemistry
• Spectrophotometry
• Chelating agent

Coordination Chemistry
Main concepts
Coordination complex Ligand Coordination number Chelation Crystal field theory Ligand field theory Isomerism in coordination complexes
Types of ligands
Monodentate ligand Bidentate ligand Polydentate ligand Ambidentate ligand Bridging ligand
Applications
Bioinorganic chemistry Catalysis Medicinal chemistry Materials science
Notable complexes
Hemoglobin Chlorophyll Cisplatin Ferrocene
Related topics
Inorganic chemistry Organometallic chemistry Transition metal Metal complex