cis-Diamminediiodoplatinum(II)
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| Other names
cis-Diiododiammineplatinum, cis-Platinumdiammine diiodide
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.036.452 |
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PubChem CID
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| Properties | |
| H6I2N2Pt | |
| Molar mass | 482.955 g·mol−1 |
| Appearance | red-orange solid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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cis-Diamminediiodoplatinum(II) is a coordination complex of platinum(II) with the formula cis-[PtI2(NH3)2]. It is a red solid. Its structure has been confirmed by X-ray crystallography.[1] It is the usual precursor to a popular anticancer drug cisplatin, cis-[PtCl2(NH3)2].[2]
Synthesis
Its synthesis entails the reaction of ammonia with potassium tetraiodoplatinate, generated in situ via the reaction of potassium tetrachloroplatinate with potassium iodide:[3]
- [PtI4]2− + 2 NH3 → cis-[PtI2(NH3)2] + 2 I−
In this conversion, the addition of the second ammonia ligand is governed by the trans effect.[4][2]
A variety of related alkylamine complexes can be prepared similarly.[5][6]
Reactions
Of commercial interest, cis-[PtI2(NH3)2] reacts with aqueous silver nitrate to give the diaquo complex, which subsequently can be converted to cisplatin:[2][3]
- cis-[PtI2(NH3)2] + 2 Ag+ + 2 H2O → cis-[Pt(H2O)2(NH3)2]2+ + 2 AgI
- cis-[Pt(H2O)2(NH3)2]2+ + 2 Cl− → cis-[PtCl2(NH3)2] + 2 H2O
cis-[PtI2(NH3)2] reacts with perchloric acid to undergo deamination, giving the dimeric iodo-bridged complex:[7]
- 2 cis-[PtI2(NH3)2] + 2 HClO4 → [Pt2I4(NH3)2] + 2 NH4ClO4
This dimeric complex can then be aminated:[7]
- [Pt2I4(NH3)2] + 2 RNH2 → 2 cis-[PtI2(NH3)(H2NR)]
Oxidative addition of iodine to cis-[PtI2(NH2)2] gives the trans Pt(IV) derivative:[5]
- cis-[PtI2(NH3)2] + I2 → trans-[PtI4(NH3)2]
References
- ^ Raudaschl-Sieber, Gabriele; Lippert, Bernhard; Britten, James F.; Beauchamp, Andre L. (1986). "N,N-dimethylacetamide adducts of mixed iodo-ammine complexes of platinum(II) and platinum(IV)". Inorganica Chimica Acta. 124 (4): 213–217. doi:10.1016/S0020-1693(00)83294-6.
- ^ a b c Wilson, J. J.; Lippard, S. J. (2014). "Synthetic methods for the preparation of platinum anticancer complexes". Chemical Reviews. 114 (8): 4470–4495. doi:10.1021/cr4004314. PMC 3999256. PMID 24283498.
- ^ a b Dhara, S. C. (1970). "A Rapid Method for the Synthesis of cis-[Pt(NH3)2Cl2]". Indian Journal of Chemistry. 8 (2): 193–194. hdl:2027/uc1.l0075121756. ISSN 0019-5103. OCLC 01752896.
- ^ Alderden RA, Hall MD, Hambley TW (2006). "The Discovery and Development of Cisplatin". J. Chem. Educ. 83 (5): 728. Bibcode:2006JChEd..83..728A. doi:10.1021/ed083p728. S2CID 29546931.
- ^ a b Messori, Luigi; Casini, Angela; Gabbiani, Chiara; Michelucci, Elena; Cubo, Leticia; Ríos-Luci, Carla; Padrón, José M.; Navarro-Ranninger, Carmen; Quiroga, Adoracion G. (2010). "Cytotoxic Profile and Peculiar Reactivity with Biomolecules of a Novel "Rule-Breaker" Iodidoplatinum(II) Complex". ACS Medicinal Chemistry Letters. 1 (8): 381–385. doi:10.1021/ml100081e. PMC 4007831. PMID 24900222.
- ^ Marzo, Tiziano; Pillozzi, Serena; Hrabina, Ondrej; Kasparkova, Jana; Brabec, Viktor; Arcangeli, Annarosa; Bartoli, Gianluca; Severi, Mirko; Lunghi, Alessandro; Totti, Federico; Gabbiani, Chiara; Quiroga, Adóracion G.; Messori, Luigi (2015). "cis-Pt I2(NH3)2: a reappraisal". Dalton Transactions. 44 (33): 14896–14905. doi:10.1039/c5dt01196e. PMID 26226326.
- ^ a b Rochon, F. D.; Kong, P. C. (1986). "Iodo-bridged complexes of platinum(II) and synthesis of cis mixed-amine platinum(II) compounds". Canadian Journal of Chemistry. 64 (9): 1894–1896. doi:10.1139/v86-312.