Phenanthroline

Phenanthroline
Phenanthroline
Identifiers
CAS number 66-71-7 YesY
ChemSpider 1278 YesY
DrugBank DB02365
ChEBI CHEBI:44975 N
ChEMBL CHEMBL415879 YesY
RTECS number SF8300000
Jmol-3D images Image 1
Properties
Molecular formula C12H8N2
Molar mass 180.21 g/mol
Appearance colourless crystals
Density 1.31 g/cm3
Melting point

117 °C, 390 K, 243 °F

Solubility in water moderate
Solubility in other solvents acetone
Hazards
R-phrases R25, R50/53
S-phrases S45,S60,S61
Main hazards mild neurotoxin, strong nephrotoxin, and powerful diuretic
Related compounds
Related compounds 2,2'-bipyridine
ferroin
phenanthrene
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Phenanthroline (phen) is a heterocyclic organic compound. As a bidentate 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).

Contents

Synthesis

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.[1] Dehydration of glycerol gives acrolein which condenses with the amine followed by a cyclization.

Peptidase inhibitor

1,10-Phenanthroline is an inhibitor of metallopeptidases, with one of the first observed instances reported in carboxypeptidase A.[2] 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.[3]

Ferroin and analogues

The complex [Fe(phen)3]2+, called "ferroin," is used for the photometric determination of Fe(II).[4] 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.[5] 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.[6] The analogous [Ru(phen)3]2+ has long been known to be bioactive.[7]

Related ligands

In the related compound "bathophenanthroline," the 4 and 7 positions are substituted by phenyl groups.

As an indicator for alkyl lithium reagents

Alkyl lithium reagents form deeply colored derivatives with phenanthroline. The alkyl lithium 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.[8]

Grignard reagents may be similarly titrated.[9]

References

  1. ^ 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. 
  2. ^ 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. 
  3. ^ Salvesen, GS & Nagase, H (2001). "Inhibition of proteolytic enzymes". Proteolytic enzymes: a practical approach, 2 edn 1: 105–130. 
  4. ^ Belcher, R. "Application of chelate Compounds in Analytical Chemistry" Pure and Applied Chemistry, 1973, volume 34, pages 13-27.
  5. ^ 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.  edit
  6. ^ 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. 
  7. ^ 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. 
  8. ^ Paul J. Fagan and William A. Nugent (1998), "1-Phenyl-2,3,4,5-Tetramethylphosphole", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV9P0653 ; Coll. Vol. 9: 653 
  9. ^ 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. 

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Look at other dictionaries:

  • Phenanthroline — Phe*nan thro*line, n. [Phenanthrene + quinoline.] (Chem.) Either of two metameric nitrogenous hydrocarbon bases, {C12H8N2}, analogous to phenanthridine, but more highly nitrogenized. [1913 Webster] …   The Collaborative International Dictionary of English

  • phenanthroline — fenantrolinas statusas T sritis chemija apibrėžtis Heterociklinis junginys. formulė C₁₂H₈N₂ atitikmenys: angl. phenanthroline rus. фенантролин ryšiai: sinonimas – diazofenantrenas …   Chemijos terminų aiškinamasis žodynas

  • phenanthroline — noun A tricyclic heterocyclic compound having two pyridine rings fused with a benzene ring; any of its derivatives …   Wiktionary

  • phenanthroline — phe·nan·thro·line …   English syllables

  • phenanthroline — fə̇ˈnan(t)thrəˌlēn, lə̇n noun ( s) Etymology: International Scientific Vocabulary phenanthr + quinoline : any of three crystalline nitrogen bases C12H8N2 related to phenanthrene and derivable from ortho , meta , and para phenylenediam …   Useful english dictionary

  • o-phenanthroline — o phe·nan·thro·line (fə nanґthrə lēn) the ortho (1,10) isomeric form of phenanthroline, it is a metal chelator often used as an indicator …   Medical dictionary

  • C12H8N2 — Phenanthroline Phe*nan thro*line, n. [Phenanthrene + quinoline.] (Chem.) Either of two metameric nitrogenous hydrocarbon bases, {C12H8N2}, analogous to phenanthridine, but more highly nitrogenized. [1913 Webster] …   The Collaborative International Dictionary of English

  • Neocuproine — IUPAC name 2,9 dimethyl 1,10 phenanthroline …   Wikipedia

  • Hypofluorous acid — Chembox new Name = Hypofluorous acid ImageFile = Hypofluorous acid 2D dimensions.png ImageName = Hypofluorous acid ImageFile1 = Hypofluorous acid 3D vdW.png ImageName1 = Hypochlorous acid IUPACName = hypofluorous acid OtherNames = hydrogen… …   Wikipedia

  • 1,10-phénantroline — Orthophénanthroline Général Nom IUPAC 1,10 phénanthroline No CAS …   Wikipédia en Français

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