Phenanthroline
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| Phenanthroline | |
|---|---|
 |
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| IUPAC name | 1,10-phenanthroline |
| Identifiers | |
| CAS number | [66-71-7] |
| RTECS number | SF8300000 |
| SMILES | c1ccnc3c1ccc2cccnc23 |
| Properties | |
| Molecular formula | C12H8N2 |
| Molar mass | 180.3 g/mol |
| Appearance | colourless crystals |
| Density | ? g/cm3 |
| Melting point |
117 °C |
| Solubility in water | low |
| Solubility in other solvents | ethanol |
| Hazards | |
| Main hazards | toxic |
| R-phrases | R25, R50/53 |
| S-phrases | S45,S60,S61 |
| Related compounds | |
| Related compounds | 2,2'-bipyridine ferroin phenanthrene |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Phenanthroline is a heterocyclic organic compound. As a bidentate ligand in coordination chemistry, commonly abbreviated "phen," it forms strong complexes with most metal ions. In terms of its coordination properties, phen is similar to 2,2'-bipyridine.
Contents |
[edit] Ferroin and analogues
The complex [Fe(phen)3]2+, , called "ferroin," is used for the photometric determination of Fe(II).[1] It is used as a redox indicator with standard potential +1.06 V. The reduced ferrous form has a deep red colour and the oxidised form is light-blue. Ferroin is used as a cell permeable inhibitor for metalloproteases in cell biology.
The pink complex [Ni(phen)3]2+ has been resolved into its Δ and Λ isomers.[2] The analogous [Ru(phen)3]2+ has long been known to be bioactive.[3]
[edit] Related ligands
In the related compound "bathophenanthroline," the 4 and 7 positions are substituted by phenyl groups.
[edit] As an indicator for alkyl lithium reagents
Alkyl lithium reagents form deeply colored derivatives with phen. The alkyl lithium content of solutions can be determined by treatment of such reagents with small amounts of phen (ca. 1 mg) followed by titration with alcohols to a colourless endpoint.[4]
[edit] References
- ^ Belcher, R. "Application of chelate Compounds in Analytical Chemistry" Pure and Applied Chemistry, 1973, volume 34, pages 13-27.
- ^ "Resolution of the tris-(1,10-Phenanthroline)Nickel(II) Ion" George B. Kauffman, Lloyd T. Takahashi, Inorganic Syntheses 1966, V, 227-232. ISBN: 9780470131671
- ^ F. P. Dwyer, E. C. Gyarfas, W. P. Rogers, J. H. Koch "Biological Activity of Complex Ions" Nature 170, 190-191 (2 August 1952). doi:10.1038/170190a0
- ^ Paul J. Fagan and William A. Nugent (1998). "1-Phenyl-2,3,4,5-Tetramethylphosphole". Org. Synth.; Coll. Vol. 9: 653.
| Phenanthroline Fe(II) (Redox indicator) | ||
| E0= 1.06V | ||
| Reduced | ↔ | Oxidized |
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