| 词条 | Phenanthroline | |||||||||||||||||||||||||
| 释义 |
| Verifiedimages = changed | Watchedfields = changed | verifiedrevid = 464199880 | Name = Phenanthroline | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = 1,10-phenanthroline.svg | ImageName = 1,10-phenanthroline | ImageFile1 = Sample of 1,10-Phenanthroline.jpg | ImageName1 = Sample of 1,10-Phenanthroline | PIN = 1,10-Phenanthroline[1] |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 1278 | InChI = 1/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H | InChIKey = DGEZNRSVGBDHLK-UHFFFAOYAW | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 415879 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DGEZNRSVGBDHLK-UHFFFAOYSA-N | CASNo = 66-71-7 | CASNo_Ref = {{cascite|correct|CAS}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB02365 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 44975 | SMILES = c1cc2ccc3cccnc3c2nc1 | RTECS = SF8300000 |Section2={{Chembox Properties | Formula = C12H8N2 | MolarMass = 180.21 g/mol | Appearance = colourless crystals | Density = 1.31 g/cm3 | Solubility = moderate | Solvent = other solvents | SolubleOther = acetone ethanol | MeltingPtC = 117 | BoilingPt = | pKa = 4.86 (phenH+)[2] |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = mild neurotoxin, strong nephrotoxin, and powerful diuretic | RPhrases = {{R25}}, {{R50/53}} | SPhrases = {{S45}},{{S60}},{{S61}} |Section8={{Chembox Related | OtherCompounds = 2,2'-bipyridine ferroin phenanthrene }}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, forming strong complexes with most metal ions.[3] SynthesisPhenanthroline 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.[4] Dehydration of glycerol gives acrolein which condenses with the amine followed by a cyclization. Coordination chemistryIn terms of its coordination properties, phenanthroline is similar to 2,2'-bipyridine (bipy) but binds metals more tightly since the chelating nitrogen donors are preorganized. Phenanthroline is however a weaker donor than bipy.[5] Many homoleptic complexes are known. Particularly well studied is [Fe(phen)3]2+, called "ferroin." It was used for the photometric determination of Fe(II).[6] 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.[7] The pink complex [Ni(phen)3]2+ has been resolved into its Δ and Λ isomers.[8] Copper(I) forms [Cu(phen)2]+, which is luminescent.[9][10] Bioinorganic chemistryThe ferroin analogue [Ru(phen)3]2+ has long been known to be bioactive.[10] 1,10-Phenanthroline is an inhibitor of metallopeptidases, with one of the first observed instances reported in carboxypeptidase A.[11] 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.[12] Related phen ligands
A variety of substituted derivatives of phen have been examined as ligands.[15] Substituents at the 2,9 positions confer protection for the attached metal, inhibiting the binding of multiple equivalents of the phenanthroline. Phen itself form complexes of the type [M(phen)3]Cl2 when treated with metal dihalides (M = Fe, Co, Ni). By contrast, neocuproine and bathocuproine form 1:1 complexes such as [Ni(neo/batho-cuproine)Cl2]2.[16] As an indicator for alkyllithium reagentsAlkyllithium 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.[17] Grignard reagents may be similarly titrated.[18] References1. ^{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 211 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}} {{Peptide receptor modulators}}2. ^Durand, J., et al., "Long-Lived Palladium Catalysts for Co/Vinyl Arene Polyketones Synthesis: A Solution to Deactivation Problems", Chemistry – A European Journal 2006, volume 12, 7639-7651. {{DOI|10.1002/chem.200501047}} 3. ^C.R. Luman, F.N. Castellano "Phenanthroline Ligands" in Comprehensive Coordination Chemistry II, 2003, Elsevier. {{ISBN|978-0-08-043748-4}}. 4. ^{{cite journal |author1=B. E. Halcrow |author2=W. O. Kermack | journal = J. Chem. Soc. | pages = 155–157 | year = 1946 | doi = 10.1039/jr9460000155 | title = 43. Attempts to find new antimalarials. Part XXIV. Derivatives of o-phenanthroline (7 : 8 : 3′ : 2′-pyridoquinoline)}} 5. ^{{cite journal|last1=Teng|first1=Qiaoqiao|last2=Huynh|first2=Han Vinh|title=A unified ligand electronic parameter based on C NMR spectroscopy of N-heterocyclic carbene complexes|journal=Dalton Transactions|date=2017|volume=46|issue=3|pages=614–627|doi=10.1039/C6DT04222H}} 6. ^Belcher, R. "Application of chelate Compounds in Analytical Chemistry" Pure and Applied Chemistry, 1973, volume 34, pages 13-27. 7. ^{{Cite journal | last1 = Bellér | first1 = G. B. | last2 = Lente | first2 = G. B. | last3 = Fábián | first3 = I. N. | title = Central Role of Phenanthroline Mono-N-oxide in the Decomposition Reactions of Tris(1,10-phenanthroline)iron(II) and -iron(III) Complexes | journal = Inorganic Chemistry | volume = 49 | issue = | pages = 3968–3970 | year = 2010 | pmid = 20415494 | doi = 10.1021/ic902554b}} 8. ^{{cite journal | title = Resolution of the tris-(1,10-Phenanthroline)Nickel(II) Ion | author = George B. Kauffman, Lloyd T. Takahashi | journal = Inorg. Synth. | year = 1966 | volume = 5 | pages = 227–232|doi=10.1002/9780470132395.ch60}} 9. ^Armaroli, N., "Photoactive Mono- and Polynuclear Cu(I)-Phenanthrolines. A Viable Alternative to Ru(Ii)-Polypyridines?", Chemical Society Reviews 2001, volume 30, 113-124.{{DOI|10.1039/b000703j}} 10. ^{{cite journal |author1=F. P. Dwyer |author2=E. C. Gyarfas |author3=W. P. Rogers |author4=J. H. Koch | title = Biological Activity of Complex Ions | journal = Nature | volume = 170 | pages = 190–191 | year = 1952 | doi = 10.1038/170190a0 | pmid=12982853 | issue=4318}} 11. ^{{Cite journal | doi = 10.1021/bi00908a006 | author = Felber, JP, Coombs, TL & Vallee, BL | title = The mechanism of inhibition of carboxypeptidase A by 1,10-phenanthroline | journal = Biochemistry | year = 1962 | volume = 1 | pages = 231–238 | pmid = 13892106 | issue = 2}} 12. ^{{cite journal |author1=Salvesen, GS |author2=Nagase, H |lastauthoramp=yes | title = Inhibition of proteolytic enzymes | journal = Proteolytic enzymes: a practical approach, 2 edn | year = 2001 | volume = 1 | pages = 105–130}} 13. ^{{Cite journal | title = Kinetics of the substitution of acetylacetone in acetylactonato-1,5-cyclooctadienerhodium(I) by derivatives of 1,10-phenantrholine and 2,2′-dipyridyl | authors = J. G. Leipoldt, G. J. Lamprecht, E. C.Steynberg | journal = Journal of Organometallic Chemistry | year = 1991| volume = 402| pages = 259–263 | doi = 10.1016/0022-328X(91)83069-G}} 14. ^{{cite encyclopedia|encyclopedia=eEROS|title=|author=Ryan A. Altman|year=2008|doi=10.1002/047084289X.rn00918}} 15. ^1 Pallenberg, A. J.; Koenig, K. S.; Barnhart, D. M., "Synthesis and Characterization of Some Copper(I) Phenanthroline Complexes", Inorg. Chemistry 1995, volume 34, 2833-2840. {{doi|10.1021/ic00115a009}} 16. ^{{cite journal|authors=Preston, H. S.; Kennard, C. H. L.|title=Crystal Structure of di-mu-Chloro-sym-trans-Dichloro-Bis-(2,9-Dimethyl-1,10-Phenanthroline)dinickel(II)-2-Chloroform|journal=J. Chem. Soc. A|year=1969|pages=2682–2685|doi=10.1039/J19690002682}} 17. ^{{OrgSynth | author = Paul J. Fagan and William A. Nugent | title = 1-Phenyl-2,3,4,5-Tetramethylphosphole| collvol = 9 | collvolpages = 653| year = 1998 | prep = CV9P0653}} 18. ^{{cite journal |author1=Ho-Shen Lin |author2=Leo A. Paquette | title = A Convenient Method for Determining the Concentration of Grignard Reagents | journal = Synth. Commun. | volume = 24 | pages = 2503–2506 | year = 1994 | doi = 10.1080/00397919408010560 | issue =17}} 3 : Redox indicators|Chelating agents|Phenanthrolines |
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