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Zeise's salt
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<h2 id="preparation">Preparation</h2> <p>This compound is commercially available as a hydrate. The hydrate is commonly prepared from <a href="/facts/Potassium_tetrachloroplatinate/G3LUIm02">K2[PtCl4]</a> and <a href="/facts/Ethylene/QMNBYLYn">ethylene</a> in the presence of a <a href="/facts/Catalyst/LPBS7TQC">catalytic</a> amount of <a href="/facts/Tin(II)_chloride/4TdjMLEk">SnCl2</a>. The water of hydration can be removed <i>in vacuo</i>.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a> </p> <h2 id="structure">Structure</h2> <p>The alkene C=C bond is approximately perpendicular to the PtCl3 plane.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a><a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> In Zeise's salt and related compounds, the alkene rotates about the metal-alkene bond with a modest <a href="/facts/Activation_energy/GqkgPvo0">activation energy</a>. Analysis of the barrier heights indicates that the π-bonding between most metals and the alkene is weaker than the σ-bonding. In Zeise's anion, this rotational barrier has not been assessed. </p> <h2 id="history">History</h2> <p>Zeise's salt was one of the first <a href="/facts/Organometallic_chemistry/bhqFz2P0">organometallic</a> compounds to be reported.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> It was discovered by <a href="/facts/William_Christopher_Zeise/yWttfNx4">William Christopher Zeise</a>, a professor at the <a href="/facts/University_of_Copenhagen/GdnhESXv">University of Copenhagen</a>, who prepared this compound in 1830 while investigating the reaction of <a href="/facts/Platinum(IV)_chloride/55qXRQsk">PtCl4</a> with boiling <a href="/facts/Ethanol/3lCLfBSP">ethanol</a>. Following careful analysis he proposed that the resulting compound contained <a href="/facts/Ethylene/QMNBYLYn">ethylene</a>. <a href="/facts/Justus_von_Liebig/0vKzMlDA">Justus von Liebig</a>, a highly influential chemist of that era, often criticised Zeise's proposal, but Zeise's proposal was decisively supported in 1868 when Birnbaum prepared the complex using ethylene.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> Zeise's salt received a great deal of attention during the second half of the 19th century because chemists could not explain its <a href="/facts/Molecular_structure/N9ljSfFq">molecular structure</a>. This question remained unanswered until the determination of its <a href="/facts/X-ray_crystallography/WtI0F5DN">X-ray crystal structure</a> in the 20th century.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a><a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> Zeise's salt stimulated much scientific research in the field of <a href="/facts/Organometallic_chemistry/bhqFz2P0">organometallic chemistry</a> and would be key in defining new concepts in chemistry. The <a href="/facts/Dewar%E2%80%93Chatt%E2%80%93Duncanson_model/h7VTIqyV">Dewar–Chatt–Duncanson model</a> explains how the metal is coordinated to the C=C double bond.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a><a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a><a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a> </p> <h2 id="related-compounds">Related compounds</h2> <ul><li>Zeise's dimer, [(<i>η</i>2-C2H4)PtCl2]2, derived from Zeise's salt by elimination of KCl followed by dimerisation.</li> <li>COD-platinum dichloride, <a href="/facts/Dichloro(cycloocta-1,5-diene)platinum(II)/JIoGGP0k">(cyclooctadiene)PtCl2</a>, derived from <a href="/facts/Platinum(II)_chloride/Cclhm6m2">platinum(II) chloride</a> and <a href="/facts/1,5-cyclooctadiene/NjXGaL8t">1,5-cyclooctadiene</a>, is a common platinum(II) alkene complex.</li></ul> <p>Many other ethylene complexes have been prepared. For example, ethylenebis(triphenylphosphine)platinum(0), [(C6H5)3P]2Pt(H2C=CH2), wherein the platinum is three-coordinate and in <a href="/facts/Oxidation_state/W53W6s6V">oxidation state</a> 0 (Zeise's salt is a derivative of platinum(II)). </p> <ul><li>Dichloro(ethylene)(α-<a href="/facts/Methylbenzylamine/1WlQczGI">methylbenzylamine</a>)platinum(II) (PtCl2(C2H4)(PhCH(NH2)Me) is a chiral derivative of Zeise's salt that is used for the <a href="/facts/Chiral_resolution/tu0AIqGg">chiral resolution</a> of alkenes.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Chock, P. B.; Halpern, J.; Paulik, F. E.; Shupack, Saul I.; Deangelis, Thomas P. (January 1990). "Potassium Trichloro(Ethene)Platinate(II) (Zeise's Salt)". Inorganic Syntheses. Vol. 28. pp. 349–351. doi:10.1002/9780470132593.ch90. ISBN 978-0-471-52619-3. OCLC 86223997. <a href="978-0-471-52619-3" target="_blank">978-0-471-52619-3</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Black, M.; Mais, R. H. B.; Owston, P. G. (1969). "The crystal and molecular structure of Zeise's salt, KPtCl3·C2H4·H2O". Acta Crystallogr. B25 (9): 1753–1759. doi:10.1107/S0567740869004699. <a href="/wiki/P._G._Owston" target="_blank">/wiki/P._G._Owston</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Love, R. A.; Koetzle, T. F.; Williams, G. J. B.; Andrews, L. C.; Bau, R. (1975). "Neutron diffraction study of the structure of Zeise's salt, KPtCl3·C2H4·H2O". Inorg. Chem. 14 (11): 2653–2657. doi:10.1021/ic50153a012. <a href="/wiki/Inorganic_Chemistry_(journal)" target="_blank">/wiki/Inorganic_Chemistry_(journal)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Zeise, W. C. (1831). "Von der Wirkung zwischen Platinchlorid und Alkohol, und von den dabei entstehenden neuen Substanzen" [On the reaction between platinum chloride and alcohol, and its resulting new substances]. Ann. Phys. Chem. (in German). 97 (4): 497–541. Bibcode:1831AnP....97..497Z. doi:10.1002/andp.18310970402. <a href="/wiki/William_Christopher_Zeise" target="_blank">/wiki/William_Christopher_Zeise</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Hunt, L. B. (1984). "The First Organometallic Compounds: William Christopher Zeise and His Platinum Complexes". Platin. Met. Rev. 28 (2): 76–83. doi:10.1595/003214084X2827683. S2CID 100304495. Archived from the original on 2023-05-22. Retrieved 2022-09-28. <a href="https://web.archive.org/web/20230522193944/https://technology.matthey.com/documents/496120/626258/pmr-v28-i2-076-083.pdf/bcda1a2a-3ef1-cbda-19a7-062e2dabd43e?version=1.0&t=1656013811978" target="_blank">https://web.archive.org/web/20230522193944/https://technology.matthey.com/documents/496120/626258/pmr-v28-i2-076-083.pdf/bcda1a2a-3ef1-cbda-19a7-062e2dabd43e?version=1.0&t=1656013811978</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Black, M.; Mais, R. H. B.; Owston, P. G. (1969). "The crystal and molecular structure of Zeise's salt, KPtCl3.C2H4.H2O". Acta Crystallogr. B. 25 (9): 1753–1759. Bibcode:1969AcCrB..25.1753B. doi:10.1107/S0567740869004699. <a href="/wiki/P._G._Owston" target="_blank">/wiki/P._G._Owston</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Jarvis, J. A. J.; Kilbourn, B. T.; Owston, P. G. (1971). "A Re-determination of the Crystal and Molecular Structure of Zeise's salt, KPtCl3.C2H4.H2O". Acta Crystallogr. B. 27 (2): 366–372. Bibcode:1971AcCrB..27..366J. doi:10.1107/S0567740871002231. <a href="/wiki/P._G._Owston" target="_blank">/wiki/P._G._Owston</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Mingos, D. Michael P. (2001). "A Historical Perspective on Dewar's Landmark Contribution to Organometallic Chemistry". J. Organomet. Chem. 635 (1–2): 1–8. doi:10.1016/S0022-328X(01)01155-X. <a href="/wiki/Michael_Mingos" target="_blank">/wiki/Michael_Mingos</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Winterton, N. (2002). "Some Notes on the Early Development of Models of Bonding in Olefin-Metal Complexes". In Leigh, G. J.; Winterton, N. (eds.). Modern Coordination Chemistry: The Legacy of Joseph Chatt. RSC Publishing. pp. 103–110. ISBN 978-0-85404-469-6. <a href="978-0-85404-469-6" target="_blank">978-0-85404-469-6</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>Astruc, Didier (2007). Organometallic Chemistry and Catalysis. Springer. pp. 41–43. ISBN 978-3-540-46128-9. <a href="978-3-540-46128-9" target="_blank">978-3-540-46128-9</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Steven D. Paget (2001). "(−)-Dichloro(ethylene)(α-methylbenzylamine)platinum(II)". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rd119. ISBN 0-471-93623-5. <a href="0-471-93623-5" target="_blank">0-471-93623-5</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> </ol>