| Revision as of 04:43, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,054 edits Saving copy of the {{chembox}} taken from revid 460890659 of page Allylpalladium_chloride_dimer for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 20:10, 6 August 2024 edit JWBE (talk | contribs)Extended confirmed users10,129 edits removed Category:Metal halides using HotCat |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 428818160 |
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|verifiedrevid = 477314020 |
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| Name = Allylpalladium(II) chloride dimer |
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| ImageFile1 = Allylpalladium-chloride-dimer-3D-balls.png |
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|Name = Allylpalladium(II) chloride dimer |
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|ImageFile1 = Allylpalladium-chloride-dimer-3D-balls.png |
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| ImageFile2 = -AllPdCl-2.png |
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| ImageSize1 = 180 |
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|ImageFile2 = -AllPdCl-2.png |
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| IUPACName = Allylpalladium(II) chloride dimer |
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| ImageSize2 = 190 |
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|IUPACName = Allylpalladium(II) chloride dimer |
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| OtherNames = Allylpalladium chloride dimer<br /> bis(allyl)di-μ-chloro-dipalladium(II)<br /> APC |
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|OtherNames = Allylpalladium chloride dimer<br /> bis(allyl)di-μ-chloro-dipalladium(II)<br /> APC |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 21171401 |
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|ChemSpiderID = 21171401 |
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|EC_number = 234-579-8 |
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| InChI = 1/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q;;;;2*+1/p-2/r2C3H5ClPd/c2*1-2-3-5-4/h2*2H,1,3H2 |
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|DTXSID = DTXSID10897423 |
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| SMILES = ClCC=C.C=CCCl |
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|InChI = 1/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q;;;;2*+1/p-2/r2C3H5ClPd/c2*1-2-3-5-4/h2*2H,1,3H2 |
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| InChIKey = TWKVUTXHANJYGH-NNVIZEFPAF |
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|SMILES = ClCC=C.C=CCCl |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|InChIKey = TWKVUTXHANJYGH-NNVIZEFPAF |
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| StdInChI = 1S/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q;;;;2*+1/p-2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q;;;;2*+1/p-2 |
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| StdInChIKey = TWKVUTXHANJYGH-UHFFFAOYSA-L |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = TWKVUTXHANJYGH-UHFFFAOYSA-L |
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| CASNo = 12012-95-2 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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}} |
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|CASNo = 12012-95-2 |
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| Section2 = {{Chembox Properties |
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|PubChem = 61538 |
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| Formula = C<sub>6</sub>H<sub>10</sub>Cl<sub>2</sub>Pd<sub>2</sub> |
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| MolarMass = 365.85 g/mol |
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| Appearance = Pale yellow, crystalline solid |
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| Density = Solid |
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| Solubility = Insoluble |
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| Solvent = other solvents |
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| SolubleOther = ]<br />]<br />]<br />] |
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| MeltingPt = decomp at 155-156 °C |
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}} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = http://www.colonialmetals.com/pdf/5048.pdf |
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| RPhrases = 36/37/38 |
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| SPhrases = 26-36 |
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}} |
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| Section8 = {{Chembox Related |
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| Function = compounds |
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| OtherFunctn = (η<sup>3</sup>-allyl)(η5 – cyclopentadienyl)palladium(II)<br /> di-μ-chlorobis(crotyl)dipalladium |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = C<sub>6</sub>H<sub>10</sub>Cl<sub>2</sub>Pd<sub>2</sub> |
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|MolarMass = 365.85 g/mol |
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|Appearance = Pale yellow, crystalline solid |
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|Density = |
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|Solubility = Insoluble |
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|Solvent = other solvents |
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|SolubleOther = ]<br />]<br />]<br />] |
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|MeltingPt = decomp at 155-156 °C |
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}} |
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|Section3={{Chembox Structure |
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|Structure_ref = <ref name="structure"/> |
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|CrystalStruct = monoclinic |
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|SpaceGroup = P2<sub>1</sub>/n, No. 14 |
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|UnitCellFormulas = 2 |
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}} |
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|Section7={{Chembox Hazards |
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|ExternalSDS = http://www.colonialmetals.com/pdf/5048.pdf |
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|GHSPictograms = {{GHS07}} |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|302|312|315|319|332|335}} |
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|PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|305+351+338|312|321|322|330|332+313|337+313|362|363|403+233|405|501}} |
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}} |
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|Section8={{Chembox Related |
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|OtherFunction_label = compounds |
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|OtherFunction = (η<sup>3</sup>-allyl)(η5 – cyclopentadienyl)palladium(II)<br /> di-μ-chlorobis(crotyl)dipalladium |
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}} |
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}} |
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'''Allylpalladium(II) chloride dimer''' (APC) is a ] with the ] ]<sup>3</sup>-C<sub>3</sub>H<sub>5</sub>)PdCl]<sub>2</sub>. This yellow air-stable compound is an important ] used in ].<ref name=Tatsuno>Tatsuno, Y.; Yoshida, T.; Otsuka, S. "(η<sup>3</sup>-allyl)palladium(II) Complexes" ], 1990, volume 28, pages 342-345. {{ISBN|0-471-52619-3}}</ref> It is one of the most widely used ]es. |
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== Structure == |
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The compound has a dimeric structure that is ]. Each allyl group lies in a plane at an angle of about 111.5° to the square formed by the palladium and carbon atoms, and the Pd–C distances are all equal. Its unit cell is monoclinic.<ref name="structure">{{cite journal|last=Smith|first=A. E.|date=1965|title=The structure of the allylpalladium chloride complex (C3H5PdCl)2 at –140°C|url=http://scripts.iucr.org/cgi-bin/paper?S0365110X65000774|journal=Acta Crystallographica|volume=18|issue=3|pages=331–340|doi=10.1107/S0365110X65000774|issn=0365-110X|doi-access=free|bibcode=1965AcCry..18..331S }}</ref> |
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==Synthesis== |
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] |
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The compound is prepared by purging ] through a methanolic ] of ] (prepared from ] and ]), and ].<ref name=Tatsuno/> |
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:2 Na<sub>2</sub>PdCl<sub>4</sub> + 2 CH<sub>2</sub>=CHCH<sub>2</sub>Cl + 2 CO + 2 H<sub>2</sub>O → <sub>2</sub> + 4 NaCl + 2 CO<sub>2</sub> + 4 HCl |
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Another method is the reaction of ] with palladium(II) ], followed by ] with chloride:<ref name="e-EROS">{{Citation|last1=Godleski|first1=Stephen A.|title=Bis(allyl)di-μ-chlorodipalladium|date=2006|url=http://doi.wiley.com/10.1002/047084289X.rb098s.pub2|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|place=Chichester, UK|publisher=John Wiley & Sons, Ltd|language=en|doi=10.1002/047084289x.rb098s.pub2|isbn=978-0-471-93623-7|access-date=2020-09-06|last2=Michelet|first2=Véronique|last3=Genêt|first3=Jean-Pierre}}</ref> |
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:2 (CF<sub>3</sub>COO)<sub>2</sub>Pd + 2 CH<sub>2</sub>=CHCH<sub>3</sub> → <sub>2</sub> |
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:<sub>2</sub> + 2 Cl<sup>−</sup> → <sub>2</sub> + 2 CF<sub>3</sub>COO<sup>−</sup> |
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== Reactions == |
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APC reacts with sources of ] to give the corresponding ] ]: |
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:<sub>2</sub> + 2 NaC<sub>5</sub>H<sub>5</sub> → 2 + 2 NaCl |
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The dimer reacts with a variety of Lewis bases (:B) to form adducts (]<sup>3</sup>-C<sub>3</sub>H<sub>5</sub>)PdCl:B. Its reaction with ] and the corresponding enthalpy are: |
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:1/2 <sub>2</sub> + :NC<sub>5</sub>H<sub>5</sub> → (η<sup>3</sup>-C<sub>3</sub>H<sub>5</sub>)PdCl:NC<sub>5</sub>H<sub>5</sub> Δ''H''=−30.1 kJ.mol<sup>−1</sup> |
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This enthalpy corresponds to the enthalpy change for a reaction forming one mole of the product, (]<sup>3</sup>-C<sub>3</sub>H<sub>5</sub>)PdCl:NC<sub>5</sub>H<sub>5</sub>, from the acid dimer. |
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The dissociation energy for the Pd dimer, which is an energy contribution prior to reaction with the donor, |
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: <sub>2</sub> → 2 (η<sup>3</sup>-C<sub>3</sub>H<sub>5</sub>)PdCl |
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has been determined by the ] to be 28 kJ.mol<sup>−1</sup>. |
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APC catalyzes many organic reactions, such as ], ] to ], and decomposition of ] to reactive ]. It is also a useful precursor of other Pd catalysts.<ref name="e-EROS"/> |
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==References== |
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<references/> |
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{{Palladium compounds}} |
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] |
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] |
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] |
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] |