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Revision as of 06:11, 17 July 2011 edit98.204.48.143 (talk) →Structure and Properties: typo fix← Previous edit		Latest revision as of 18:56, 5 July 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,556 edits →Chemical properties: replace obsolete section (eclipsed)
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	{{chembox		{{chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 402129268		| verifiedrevid = 464381848
	| Name = Rhodium (II) Acetate		| Name = Rhodium(II) acetate
	| ImageFile = Rhodium(II) acetate.jpg		| ImageFile1 = Rhodium(II)-acetate-hydrate-dimer-from-xtal-1971-3D-balls.png
			| ImageFile2 = Rhodium(II) acetate.jpg
	<!-- | ImageSize = 200px -->
	| ImageName = Rhodium(II) acetate		| ImageName = Rhodium(II) acetate
	| IUPACName = Rhodium (II) acetate		| IUPACName = Rhodium(II) acetate
	| OtherNames = Dirhodium tetraacetate,<br />Tetrakis(acetato)dirhodium(II),<br />Rhodium diacetate dimer,<br />Tetrakis-(mu-acetato)dirhodium		| OtherNames = Dirhodium tetraacetate,<br />Tetrakis(acetato)dirhodium(II),<br />Rhodium diacetate dimer,<br />Tetrakis(''μ''-acetato)dirhodium
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| SMILES = 1234#()(O(C)O1)(O(C)O2)(O(C)O3)O(C)O4
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 20370		| ChemSpiderID = 20370
	| PubChem = 21674		| PubChem = 152122
	| InChI = 1/2C2H4O2.Rh/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2		| InChI = 1S/4C2H4O2.2Rh/c4*1-2(3)4;;/h4*1H3,(H,3,4);;/q;;;;2*+2/p-4
	| InChIKey = ITDJKCJYYAQMRO-NUQVWONBAE		| InChIKey = : SYBXSZMNKDOUCA-UHFFFAOYSA-J
	| SMILES = .C(=O)C.C(=O)C
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/2C2H4O2.Rh/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2		| StdInChI = 1S/2C2H4O2.Rh/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 15956-28-2		| CASNo = 15956-28-2
			| UNII_Ref = {{fdacite|correct|FDA}}
	| RTECS = VI9361000
			| UNII = NK3058Z56X
	}}
			| RTECS = VI9361000
	| Section2 = {{Chembox Properties
			| EINECS = 240-084-8
	| Formula = C<sub>8</sub>H<sub>12</sub>O<sub>8</sub>Rh<sub>2</sub>
			}}
	| MolarMass = 441.99 g/mol
			|Section2={{Chembox Properties
	| Appearance = Emerald green powder
			| Formula = C<sub>8</sub>H<sub>12</sub>O<sub>8</sub>Rh<sub>2</sub>
	| Density = 1.126 g/cm<sup>3</sup>
			| MolarMass = 441.99 g/mol
	| Solubility = soluble
			| Appearance = Emerald green powder
	| Solvent = other solvents
			| Density = 1.126 g/cm<sup>3</sup>
	| SolubleOther = polar organic solvents
	| MeltingPt = >100 °C		| Solubility = soluble
			| Solvent = other solvents
	| BoilingPt = decomposes
			| SolubleOther = polar organic solvents
	}}
			| MeltingPt = >100 °C
	| Section3 = {{Chembox Structure
			| BoilingPt = decomposes
	| Coordination = ]
			}}
	| CrystalStruct = ]
			|Section3={{Chembox Structure
	| Dipole = 0 ]
			| Coordination = ]
	}}
			| CrystalStruct = ]
	| Section7 = {{Chembox Hazards
			| Dipole = 0 ]
	| ExternalMSDS =
			}}
	| NFPA-H = 3
			|Section7={{Chembox Hazards
	| NFPA-R = 0
			| ExternalSDS =
	| NFPA-F = 0
			| NFPA-H = 3
	| FlashPt = low flammability
	| RPhrases = 36/38		| NFPA-R = 0
			| NFPA-F = 0
	| SPhrases = 15, 26, 28A, 37/39
			| FlashPt = low flammability
	}}
			| GHS_ref=<ref>{{cite web |title=Dirhodium tetraacetate |url=https://pubchem.ncbi.nlm.nih.gov/compound/152122#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=14 December 2021 |language=en}}</ref>
	| Section8 = {{Chembox Related
			| GHSPictograms = {{GHS07}}
	| OtherCpds = ]<br />]<br />
			| GHSSignalWord = Warning
	}}
			| HPhrases = {{H-phrases|315|319}}
			| PPhrases = {{P-phrases|264|280|302+352|305+351+338|321|332+313|337+313|362}}
			}}
			|Section8={{Chembox Related
			| OtherCompounds = ]<br />]
			}}
	}}		}}
	'''Rhodium(II) acetate''' is the ] with the ] ]<sub>2</sub>(AcO)<sub>4</sub>, where AcO<sup>−</sup> is the ] ion (</sub>CH<sub>3</sub>CO<sub>2</sub><sup>−</sup>). This emerald green powder is a catalyst for ] of ]s. It is also used as ] for insertion into C-H and X-H bonds (X = N/S/O) and for ] formation for ].		'''Rhodium(II) acetate''' is the ] with the ] ]<sub>2</sub>(AcO)<sub>4</sub>, where AcO<sup>−</sup> is the ] ion ({{chem|CH|3|CO|2|−}}). This dark green powder is slightly soluble in polar solvents, including water. It is used as a catalyst for ] of ]s. It is a widely studied example of a ].<ref name=Felthouse/>
	==Preparation==		==Preparation==
			Rhodium(II) acetate is usually prepared by the heating of ] ] in a methanol-] mixture. The crude product is the bis(methanol) complex, but it is easily desolvated.<ref name=Felthouse>{{cite book |doi=10.1002/9780470166307.ch2 |chapter=The Chemistry, Structure, and Metal-Metal Bonding in Compounds of Rhodium(II) |title=Progress in Inorganic Chemistry |date=1982 |last1=Felthouse |first1=Timothy R. |volume=29 |pages=73–166 |isbn=978-0-471-09370-1 }}</ref><ref>{{Cite book | last1 = Rempel | first1 = G. A. | last2 = Legzdins | first2 = P. | last3 = Smith | first3 = H. | last4 = Wilkinson | first4 = G. | title = Inorganic Syntheses | chapter = Tetrakis(acetato)dirhodium(II) and Similar Carboxylato Compounds | doi = 10.1002/9780470132449.ch16 | journal = ] | volume = 13 | pages = 90–91 | year = 1972 | isbn = 9780470132449 }}</ref>
	Rhodium(II) acetate is usually prepared by the heating hydrated ] in ] (CH<sub>3</sub>COOH):<ref>G. A. Rempel, P. Legzdins, H. Smith, G. Wilkinson, "Tetrakis(Acetato) Dirhodium (II) and Similar Carboxylato Compounds" Inorganic Syntheses, volume 13, pp 90-91. ISBN 9780470131725</ref> Rhodium(II) acetate dimer undergoes ], the replacement of the acetate group by other ]s and related groups.<ref>Doyle, M. P. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.;Wiley: New York, 2000; Chapter 5.</ref>
	:Rh<sub>2</sub>(OAc)<sub>4</sub> + 4 HO<sub>2</sub>Y → Rh<sub>2</sub>(O<sub>2</sub>Y)<sub>4</sub> + 4 HOAc
	==Structure and Properties==		==Structure and properties==
			The structure of rhodium(II) acetate features a pair of ] atoms, each with ], defined by four acetate oxygen atoms, water, and a Rh–Rh bond of length 2.39&nbsp;]. The water ] is exchangeable, and a variety of other ]s bind to the axial positions.<ref>{{Cite journal | last1 = Cotton | first1 = F. A. | last2 = Deboer | first2 = B. G. | last3 = Laprade | first3 = M. D. | last4 = Pipal | first4 = J. R. | last5 = Ucko | first5 = D. A. | title = The crystal and molecular structures of dichromium tetraacetate dihydrate and dirhodium tetraacetate dihydrate | doi = 10.1107/S0567740871004527 | journal = Acta Crystallogr B | volume = 27 | issue = 8 | pages = 1664 | year = 1971 | doi-access = }}</ref> ] and ] adopt ].
	:]
			==Chemical properties==
	The structure of rhodium(II) acetate features a pair of ] atoms, each with ], defined by four acetate oxygen atoms, a water ligand, and a Rh-Rh bond (2.39 Å.<ref>Cotton, F. A.; DeBoer, B. G.; Laprade, M. D.; Pipal, J. R.; Ucko, D. A. Acta Crystallographica 1971, B27, 1664.</ref>. ] and ] adopt similar structures.
			The dimer binds a number of classical ]s to form 2:1 adducts:
			Its ] is eclipsed by the enhanced reactivity of ], which even binds arenes and alkenes.
	==Chemical Properties==
	The application of dirhodium tetraacetate to organic synthesis was pioneered by Teyssie and co-workers.<ref>Paulissenen R.; Reimlinger, H.; Hayez, E.; Hubert, A. J.; Teyssie, P. Tetrahedron Letters 1973, volume 14: 2233</ref> A extensive library of successful transformations rapidly evolved, ranging from Rh(II)-catalyzed OH and NH insertions to ] of ]<ref>Hubert, A. J.; Feron A.; Warin, R. Teyssie, P., Tetrahedron Letters 1976, volume 17, pp.1317</ref> and ] systems.<ref>Anciaux, A. J.; Demonceau, A.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssie, P. Journal of the Chemical Society, Chem. Commun. 1980, 765</ref> Nowadays, it is used mainly as a ]. It can help distinguish between ] and ] by binding selectively to ribonucleosides at their 2' and 3' OH groups<ref>Berger, N. A.; Tarien, E.; Eichhorn, G. L. Nature New Biology 1972, volume 239, pp. 237.</ref>. Rhodium(II) acetate dimer, compared to copper(II) acetate, is more reactive and useful in differentiating ribonucleosides and deoxynucleosides because it is soluble in ] solution like water whereas copper(II) acetate only dissolves in non-aqueous solution.
			The acetate group can be replaced by other carboxylates of strong acids. The yields are nearly quantitative.
	===Selected catalytic reactions===
			Like almost all rhodium complexes, rhodium(II) acetate catalyzes many reactions such as hydrogenation and hydrosilylation. No evidence exists for mechanisms and the behavior has not motivated further work. The important observation that rhodium(II) acetate catalyzes reactions of diazo compounds has led to considerable research, but mostly focused on the trifluoroacetate or chiral derivatives.
	1. Cyclopropanation
	:]</br> through the ] of diazocarbonyl compounds, the intra- and intermolecular ] reactions occurs.
	2. Aromatic cycloaddition
	:]</br> Rhodium acetate is a very efficient catalyst for two-component ] as well as three-component 1,3-dipolar cycloaddition reactions.
	3. C-H insertion
	:]</br> Rh(II)-catalyzed ] intramolecular and regiospecific intermolecular ] into ] and ] C-H bonds is a useful method for the synthesis of a diverse range of organic compounds.
	4. Oxidation of alcohols
	:]</br> ] and ] ] were oxidized to the corresponding carbonyl compounds using tert-butyl hydroperoxide in ] amounts and Rh<sub>2</sub>(OAc)<sub>4</sub> as catalyst in ] at ambient temperature.
	5. X-H insertion (X = N/S/O)
	:]</br> Rh(II) ] reacts with ]s, ] or ] to yield the product of a formal intra- or intermolecular X-H bond (X = N/O/S) insertion via the formation of an ] ].
	==References==		==References==
			{{Reflist}}
	{{Citation style|date=September 2007}}
	{{reflist}}
	{{Rhodium compounds}}		{{Rhodium compounds}}
			{{Acetates}}
	{{DEFAULTSORT:Rhodium(Ii) Acetate}}		{{DEFAULTSORT:Rhodium(II) Acetate}}
	]		]
	]		]
			]
			]
	]