trans-Dichlorodiammineplatinum(II) is the trans isomer of the coordination complex with the formula trans-PtCl2(NH3)2, sometimes called transplatin.[1] It is a yellow solid with low solubility in water but good solubility in DMF. The existence of two isomers of PtCl2(NH3)2 led Alfred Werner to propose square planar molecular geometry.[2] It belongs to the molecular symmetry point group D2h.
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Names | |||
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IUPAC name
(SP-4-1)-diamminedichloridoplatinum(II)
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Other names
Reiset's second chloride, transplatin
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Identifiers | |||
3D model (JSmol)
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ECHA InfoCard | 100.035.422 | ||
PubChem CID
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UNII | |||
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Properties | |||
Cl2H6N2Pt | |||
Molar mass | 300.05 g·mol−1 | ||
Appearance | yellow solid | ||
low | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and reactions
editThe complex is prepared by treating [Pt(NH3)4]Cl2 with hydrochloric acid.[2]
Many of the reactions of this complex can be explained by the trans effect. It slowly hydrolyzes in aqueous solution to give the mixed aquo complex trans-[PtCl(H2O)(NH3)2]Cl. Similarly it reacts with thiourea (tu) to give colorless trans-[Pt(tu)2(NH3)2]Cl2. In contrast, the cis isomer gives [Pt(tu)4]Cl2. Oxidative addition of chlorine gives trans-PtCl4(NH3)2.
Medicinal chemistry
edittrans-Dichlorodiammineplatinum(II) has had far less impact on medicinal chemistry compared to its cis isomer, cisplatin, which is a major anticancer drug. Nonetheless, replacement of the ammonia with other ligands has led to highly active drugs that have attracted much attention.[3]
References
edit- ^ Nakata, B; Yamagata, S; Kanehara, I; Shirasaka, T; Hirakawa, K (25 June 2006). "Transplatin, a cisplatin trans-isomer, may enhance the anticancer effect of 5-fluorouracil". Journal of Experimental & Clinical Cancer Research. 25 (2): 195–200. PMID 16918130.195-200&rft.date=2006-06-25&rft_id=info:pmid/16918130&rft.aulast=Nakata&rft.aufirst=B&rft.au=Yamagata, S&rft.au=Kanehara, I&rft.au=Shirasaka, T&rft.au=Hirakawa, K&rfr_id=info:sid/en.wikipedia.org:Transplatin" class="Z3988">
- ^ a b Kauffman, George B; Cowan, Dwaine O; Slusarczuk, George; Kirschner, Stanley (1963). "cis - and trans -Dichlorodiammineplatinum(II)". Inorganic Syntheses. Vol. VII. pp. 239–245. doi:10.1002/9780470132388.ch63. ISBN 978-0-470-13238-8.239-245&rft.date=1963&rft_id=info:doi/10.1002/9780470132388.ch63&rft.isbn=978-0-470-13238-8&rft.aulast=Kauffman&rft.aufirst=George B&rft.au=Cowan, Dwaine O&rft.au=Slusarczuk, George&rft.au=Kirschner, Stanley&rfr_id=info:sid/en.wikipedia.org:Transplatin" class="Z3988">
- ^ Aris, S. M; Farrell, N. P (2009). "Towards Antitumor Active trans-Platinum Compounds". European Journal of Inorganic Chemistry. 2009 (10): 1293–1302. doi:10.1002/ejic.200801118. PMC 2821104. PMID 20161688.1293-1302&rft.date=2009&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2821104#id-name=PMC&rft_id=info:pmid/20161688&rft_id=info:doi/10.1002/ejic.200801118&rft.aulast=Aris&rft.aufirst=S. M&rft.au=Farrell, N. P&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2821104&rfr_id=info:sid/en.wikipedia.org:Transplatin" class="Z3988">