|Jmol interactive 3D||Image|
|Molar mass||180.21 g/mol|
|Melting point||117 °C (243 °F; 390 K)|
|Solubility in other solvents||acetone
|Main hazards||mild neurotoxin, strong nephrotoxin, and powerful diuretic|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phenanthroline (phen) is a heterocyclic organic compound. It is a white solid that is soluble in organic solvents. It is used as a ligand in coordination chemistry, it forms strong complexes with most metal ions. In terms of its coordination properties, phen is similar to 2,2'-bipyridine (bipy).
Phenanthroline may be prepared by two successive Skraup reactions of glycerol with o-phenylenediamine, catalyzed by sulfuric acid, and an oxidizing agent, traditionally aqueous arsenic acid or nitrobenzene. Dehydration of glycerol gives acrolein which condenses with the amine followed by a cyclization.
1,10-Phenanthroline is an inhibitor of metallopeptidases, with one of the first observed instances reported in carboxypeptidase A. Inhibition of the enzyme occurs by removal and chelation of the metal ion required for catalytic activity, leaving an inactive apoenzyme. 1,10-Phenanthroline targets mainly zinc metallopeptidases, with a much lower affinity for calcium.
Ferroin and analogues
The complex [Fe(phen)3]2+, called "ferroin," is used for the photometric determination of Fe(II). 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.
Related phen ligands
A variety of substituted derivatives of phen have been examined as ligands. Neocuproine, 2,9-dimethyl-1,10-phenanthroline, is a bulky ligand. In "bathophenanthroline," the 4 and 7 positions are substituted by phenyl groups. The more electron-rich phenanthroline ligand is 3,4,7,8-tetramethyl-1,10-phenanthroline.
As an indicator for alkyllithium reagents
Alkyllithium reagents form deeply colored derivatives with phenanthroline. The alkyllithium content of solutions can be determined by treatment of such reagents with small amounts of phenanthroline (ca. 1 mg) followed by titration with alcohols to a colourless endpoint.
- C.R. Luman, F.N. Castellano "Phenanthroline Ligands" in Comprehensive Coordination Chemistry II, 2003, Elsevier. ISBN 978-0-08-043748-4.
- B. E. Halcrow, W. O. Kermack (1946). "43. Attempts to find new antimalarials. Part XXIV. Derivatives of o-phenanthroline (7 : 8 : 3′ : 2′-pyridoquinoline)". J. Chem. Soc.: 155–157. doi:10.1039/jr9460000155.
- Felber, JP, Coombs, TL & Vallee, BL (1962). "The mechanism of inhibition of carboxypeptidase A by 1,10-phenanthroline". Biochemistry 1 (2): 231–238. doi:10.1021/bi00908a006. PMID 13892106.
- Salvesen, GS & Nagase, H (2001). "Inhibition of proteolytic enzymes". Proteolytic enzymes: a practical approach, 2 edn 1: 105–130.
- Belcher, R. "Application of chelate Compounds in Analytical Chemistry" Pure and Applied Chemistry, 1973, volume 34, pages 13-27.
- Bellér, G. �B.; Lente, G. �B.; Fábián, I. �N. (2010). "Central Role of Phenanthroline Mono-N-oxide in the Decomposition Reactions of Tris(1,10-phenanthroline)iron(II) and -iron(III) Complexes". Inorganic Chemistry 49 (9): 3968–3970. doi:10.1021/ic902554b. PMID 20415494. replacement character in
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- George B. Kauffman, Lloyd T. Takahashi (1966). "Resolution of the tris-(1,10-Phenanthroline)Nickel(II) Ion". Inorg. Synth. 5: 227–232. doi:10.1002/9780470132395.ch60.
- F. P. Dwyer, E. C. Gyarfas, W. P. Rogers, J. H. Koch (1952). "Biological Activity of Complex Ions". Nature 170 (4318): 190–191. doi:10.1038/170190a0. PMID 12982853.
- Paul J. Fagan and William A. Nugent (1998). "1-Phenyl-2,3,4,5-Tetramethylphosphole". Org. Synth.; Coll. Vol. 9, p. 653
- Ho-Shen Lin, Leo A. Paquette (1994). "A Convenient Method for Determining the Concentration of Grignard Reagents". Synth. Commun. 24 (17): 2503–2506. doi:10.1080/00397919408010560.