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{{chembox |
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{{chembox |
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| verifiedrevid = 398682803 |
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| verifiedrevid = 437377355 |
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| Reference=<ref></ref> |
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| Reference = <ref></ref> |
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|ImageFile=Zeise's-salt-anion-from-xtal-3D-balls.png |
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| ImageFile1 = Zeise's-salt-anion-from-xtal-3D-balls.png |
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| ImageFile2 = Zeise'sSalt.png |
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|ImageSize=200px |
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|IUPACName=Potassium trichloro(ethene)platinate(II) |
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| IUPACName = Potassium trichloro(ethylene)platinate(II) hydrate |
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|OtherNames= |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=16405-35-9 |
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| CASNo= 16405-35-9 |
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| PubChem=16211684 |
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| ChemSpiderID = 21241825 |
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| SMILES= |
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| EINECS = 630-445-1 |
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| PubChem= 193510 |
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| SMILES= .C=C.Cl(Cl)Cl.O |
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| InChI = 1S/C2H4.3ClH.K.H2O.Pt/c1-2;;;;;;/h1-2H2;3*1H;;1H2;/q;;;;+1;;+2/p-3 |
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| InChIKey = DCEGWIMEFFONKJ-UHFFFAOYSA-K |
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|Section2={{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| K = 1 | Pt = 1 | Cl = 3 | C = 2 | H = 4 |
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| K=1 | Pt=1 | Cl=3 | C=2 | H=6 | O=1 |
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| Appearance= |
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| Appearance=Yellow to orange crystals |
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| Density= |
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| MeltingPt= |
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| MeltingPt=220 °C |
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|Section3={{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| GHS_ref=<ref>{{cite web |title=C&L Inventory |url=https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/163581 |website=echa.europa.eu}}</ref> |
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| EUClass = {{Hazchem Xi}} |
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| RPhrases = {{R36/37/38}} |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| SPhrases = {{S26}}-{{S37/39}} |
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| HPhrases = {{H-phrases|315|319|335}} |
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| FlashPt= |
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| PPhrases = {{P-phrases|}} |
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'''Zeise's salt''', potassium trichloro(ethene)platinate(II), is the ] with the ] K<nowiki>]Cl<sub>3</sub>(C<sub>2</sub>H<sub>4</sub>)]·H<sub>2</sub>O. The anion of this air-stable, yellow, ] contains an η<sup>2</sup>-] ]. The anion features a platinum atom with a ] geometry. |
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'''Zeise's salt''', potassium trichloro(ethylene)platinate(II) hydrate, is the ] with the ] K<nowiki>]Cl<sub>3</sub>(C<sub>2</sub>H<sub>4</sub>)]·H<sub>2</sub>O. The anion of this air-stable, yellow, ] contains an ]-] ]. The anion features a platinum atom with a ] geometry. The salt is of historical importance in the area of ] as one of the first examples of a ] and is named for its discoverer, ]. |
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==Preparation== |
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==Preparation== |
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This compound is commercially available as a hydrate. The hydrate is commonly prepared from K<sub>2</sub> and ] in the presence of a ] amount of ]. The water of hydration can be removed ''in vacuo''.<ref>{{cite journal | doi = 10.1002/9780470132593.ch90 | title = Potassium Trichloro(Ethene)Platinate(II) (Zeise's Salt) | year = 1990 | last1 = Chock | first1 = P. B. | last2 = Halpern | first2 = J. | last3 = Paulik | first3 = F. E. | last4 = Shupack | first4 = Saul I. | last5 = Deangelis | first5 = Thomas P. | volume = 28 | pages = 349–351}}</ref> |
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This compound is commercially available as a hydrate. The hydrate is commonly prepared from ]] and ] in the presence of a ] amount of ]. The water of hydration can be removed ''in vacuo''.<ref>{{cite book |last1=Chock |first1=P. B. |last2=Halpern |first2=J. |last3=Paulik |first3=F. E. |last4=Shupack |first4=Saul I. |last5=Deangelis |first5=Thomas P. |chapter=Potassium Trichloro(Ethene)Platinate(II) (Zeise's Salt) |title=] |series=<!--Inorganic Syntheses-->|date=January 1990 |volume=28 |pages=349–351 |doi=10.1002/9780470132593.ch90 |isbn=978-0-471-52619-3 |oclc=86223997}}</ref> |
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==Structure== |
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==Structure== |
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The alkene C=C bond is approximately perpendicular to the PtCl<sub>3</sub> plane.<ref>{{cite journal |
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In Zeise's salt and related compounds, the alkene rotates about the metal-alkene bond with a modest ]. 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 cannot be assessed by ] because all four protons are equivalent. Lower symmetry complexes of ethylene, e.g. ]Rh(C<sub>2</sub>H<sub>4</sub>)<sub>2</sub>, are, however, suitable for analysis of the rotational barriers associated with the metal-ethylene bond.<ref>Elschenbroich, C. ”Organometallics : A Concise Introduction” (2006) Wiley-VCH: Weinheim. ISBN 978-3-527-29390-2</ref> |
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| title = The crystal and molecular structure of Zeise's salt, KPtCl<sub>3</sub>·C<sub>2</sub>H<sub>4</sub>·H<sub>2</sub>O |
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| first1= M.|last1= Black |first2=R. H. B.|last2= Mais |author3-link=P. G. Owston|first3=P. G.|last3= Owston |
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| journal = ] |
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==History== |
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| year = 1969 |
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Zeise's salt was one of the first ] compounds to be reported.<ref>{{cite journal | last1 = Zeise | first1 = W. C. | title = Von der Wirkung zwischen Platinchlorid und Alkohol, und von den dabei entstehenden neuen Substanzen | journal = Annalen der Physik und Chemie | volume = 97 | pages = 497 | year = 1831 | doi = 10.1002/andp.18310970402 | issue = 4}}</ref> Its inventor ], a professor at the ], prepared this compound in 1820s while investigating the reaction of PtCl<sub>4</sub> with boiling ], and proposed that the resulting compound contained ]. ], an influential chemist of that era, often criticised Zeise's proposal, but Zeise's theories were decisively supported in 1868 when Birnbaum prepared the complex using ethylene.<ref>{{cite journal |
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| volume = B25 |
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| title = Neutron diffraction study of the structure of Zeise's salt, KPtCl<sub>3</sub>•C<sub>2</sub>H<sub>4</sub>•H<sub>2</sub>O |
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| issue = 9 |
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| author = R. A. Love, T. F. Koetzle, G. J. B. Williams, L. C. Andrews, R. Bau |
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| pages = 1753–1759 |
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| journal = ] |
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| doi = 10.1107/S0567740869004699 |
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}}</ref><ref>{{cite journal |
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| title = Neutron diffraction study of the structure of Zeise's salt, KPtCl<sub>3</sub>·C<sub>2</sub>H<sub>4</sub>·H<sub>2</sub>O |
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| first1= R. A.|last1= Love|first2= T. F. |last2=Koetzle|first3= G. J. B. |last3=Williams |first4=L. C. |last4=Andrews |first5=R. |last5=Bau |
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| journal = ] |
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| year = 1975 |
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| year = 1975 |
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| volume = 14 |
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| volume = 14 |
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| issue = 11 |
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| issue = 11 |
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| pages = 2653–2657 |
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| pages = 2653–2657 |
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| doi = 10.1021/ic50153a012 |
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| doi = 10.1021/ic50153a012 |
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}}</ref> In Zeise's salt and related compounds, the alkene rotates about the metal-alkene bond with a modest ]. 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. |
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}}</ref><ref> |
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{{cite journal |
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==History== |
| ⚫ |
| title = The First Organometallic Compounds: WILLIAM CHRISTOPHER ZEISE AND HIS PLATINUM COMPLEXES |
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Zeise's salt was one of the first ] compounds to be reported.<ref>{{cite journal | last1 = Zeise | first1 = W. C. | authorlink = William Christopher Zeise | title = Von der Wirkung zwischen Platinchlorid und Alkohol, und von den dabei entstehenden neuen Substanzen|language=German|trans-title=On the reaction between platinum chloride and alcohol, and its resulting new substances | journal = ] | volume = 97 | pages = 497–541 | year = 1831 | doi = 10.1002/andp.18310970402 | issue = 4|bibcode = 1831AnP....97..497Z | url = https://zenodo.org/record/1423546 }}</ref> It was discovered by ], a professor at the ], who prepared this compound in 1830 while investigating the reaction of ] with boiling ]. Following careful analysis he proposed that the resulting compound contained ]. ], 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.<ref>{{cite journal |
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| author = L. B. Hunt |
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| title = The First Organometallic Compounds: William Christopher Zeise and His Platinum Complexes |
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| journal = ] |
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| first = L. B. |
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| last = Hunt |
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| journal = ] |
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| year = 1984 |
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| year = 1984 |
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| volume = 28 |
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| volume = 28 |
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| issue = 2 |
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| issue = 2 |
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| pages = 76–83 |
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| pages = 76–83 |
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| doi = 10.1595/003214084X2827683 |
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| url = http://www.platinummetalsreview.com/pdf/pmr-v28-i2-076-083.pdf |
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| s2cid = 100304495 |
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}} |
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| url = https://technology.matthey.com/documents/496120/626258/pmr-v28-i2-076-083.pdf/bcda1a2a-3ef1-cbda-19a7-062e2dabd43e?version=1.0&t=1656013811978 |
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</ref> |
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| access-date = 2022-09-28 |
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| archive-date = 2023-05-22 |
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Zeise's salt received a great deal of attention during the second half of the 19th century because chemists could not properly explain the ] of the salt. This question remained unanswered until the advent of ] in the 20th century.<ref>{{cite journal |
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| archive-url = 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 |
| ⚫ |
| title = The crystal and molecular structure of Zeise's salt, KPtCl<sub>3</sub>•C<sub>2</sub>H<sub>4</sub>•H<sub>2</sub>O |
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| url-status = dead |
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| author = M. Black, R. H. B. Mais and ] |
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}}</ref> Zeise's salt received a great deal of attention during the second half of the 19th century because chemists could not explain its ]. This question remained unanswered until the determination of its ] in the 20th century.<ref>{{cite journal|title = The crystal and molecular structure of Zeise's salt, KPtCl<sub>3</sub>.C<sub>2</sub>H<sub>4</sub>.H<sub>2</sub>O|last1 = Black|first1 = M.|last2 = Mais|first2 = R. H. B.|last3 = Owston|first3 = P. G.|authorlink3 = P. G. Owston|year = 1969|journal = ]|volume = 25|issue = 9|pages = 1753–1759|doi = 10.1107/S0567740869004699| bibcode=1969AcCrB..25.1753B }}</ref><ref>{{cite journal|title = A Re-determination of the Crystal and Molecular Structure of Zeise's salt, KPtCl<sub>3</sub>.C<sub>2</sub>H<sub>4</sub>.H<sub>2</sub>O|last1 = Jarvis|first1 = J. A. J.|last2 = Kilbourn|first2 = B. T.|last3 = Owston|first3 = P. G.|authorlink3 = P. G. Owston|journal = ]|volume = 27|issue = 2|year = 1971|pages = 366–372|doi = 10.1107/S0567740871002231|doi-access = | bibcode=1971AcCrB..27..366J }}</ref> Zeise's salt stimulated much scientific research in the field of ] and would be key in defining new concepts in chemistry. The ] explains how the metal is coordinated to the C=C double bond.<ref>{{cite journal|title = A Historical Perspective on Dewar's Landmark Contribution to Organometallic Chemistry|last = Mingos|first = D. Michael P.|authorlink = Michael Mingos|journal = ]|volume = 635|issue = 1–2|pages = 1–8|doi = 10.1016/S0022-328X(01)01155-X|year = 2001}}</ref><ref>{{cite book|title = Modern Coordination Chemistry: The Legacy of Joseph Chatt|editor1-last = Leigh|editor1-first = G. J.|editor2-last = Winterton|editor2-first = N.|year = 2002|publisher = ]|chapter = Some Notes on the Early Development of Models of Bonding in Olefin-Metal Complexes|last = Winterton|first = N.|pages = 103–110|isbn = 978-0-85404-469-6|chapter-url = https://books.google.com/books?id=VoBxtPb5zCcC&pg=PA103}}</ref><ref>{{cite book|title = Organometallic Chemistry and Catalysis|last = Astruc|first = Didier|authorlink = Didier Astruc|year = 2007|publisher = ]|pages = 41–43|isbn = 978-3-540-46128-9|url = https://books.google.com/books?id=aVyfo52-nRsC&pg=PA41}}</ref> |
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| journal = ] |
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| year = 1969 |
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| volume = B25 |
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| issue = 9 |
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| pages = 1753–1759 |
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| doi = 10.1107/S0567740869004699 |
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}}</ref> |
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Zeise's salt stimulated much scientific research in the field of ], and would be key in defining new concepts in chemistry such as '']''. The ] explains how the metal is coordinated to the double bond. |
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==Related compounds== |
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==Related compounds== |
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* Zeise's dimer , derived from Zeise's salt by elimination of KCl followed by dimerisation. |
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* Zeise's dimer, <sub>2</sub>, derived from Zeise's salt by elimination of KCl followed by dimerisation. |
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* "COD-platinum dichloride," (cyclooctadiene)PtCl<sub>2</sub>, derived from ] and ], is a common platinum(II) alkene complex. |
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* COD-platinum dichloride, ], derived from ] and ], is a common platinum(II) alkene complex. |
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Many other ethylene complexes have been prepared. For example, ethylenebis(triphenylphosphine)platinum(0), <sub>2</sub>Pt(H<sub>2</sub>C=CH<sub>2</sub>), wherein the platinum is three-coordinate and zero-valent (Zeise's salt is a derivative of platinum(II)). |
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Many other ethylene complexes have been prepared. For example, ethylenebis(triphenylphosphine)platinum(0), <sub>2</sub>Pt(H<sub>2</sub>C=CH<sub>2</sub>), wherein the platinum is three-coordinate and in ] 0 (Zeise's salt is a derivative of platinum(II)). |
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* Dichloro(ethylene)(α-])platinum(II) (PtCl<sub>2</sub>(C<sub>2</sub>H<sub>4</sub>)(PhCH(NH<sub>2</sub>)Me) is a chiral derivative of Zeise's salt that is used for the ] of alkenes.<ref>{{cite encyclopedia|chapter=(−)-Dichloro(ethylene)(α-methylbenzylamine)platinum(II)|author=Steven D. Paget|encyclopedia= ]|year=2001|publisher= John Wiley & Sons|doi=10.1002/047084289X.rd119|isbn=0-471-93623-5}}</ref> |
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==References== |
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==References== |
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{{Platinum compounds}} |
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