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	<id>https://en.formulasearchengine.com/index.php?action=history&amp;feed=atom&amp;title=Cunningham_function</id>
	<title>Cunningham function - Revision history</title>
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	<updated>2026-05-25T04:29:24Z</updated>
	<subtitle>Revision history for this page on the wiki</subtitle>
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		<title>en&gt;Rjwilmsi: /* References */Added 1 doi to a journal cite using AWB (10102)</title>
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		<updated>2014-05-07T16:51:11Z</updated>

		<summary type="html">&lt;p&gt;&lt;span class=&quot;autocomment&quot;&gt;References: &lt;/span&gt;Added 1 doi to a journal cite using &lt;a href=&quot;/index.php?title=Testwiki:AWB&amp;amp;action=edit&amp;amp;redlink=1&quot; class=&quot;new&quot; title=&quot;Testwiki:AWB (page does not exist)&quot;&gt;AWB&lt;/a&gt; (10102)&lt;/p&gt;
&lt;a href=&quot;https://en.formulasearchengine.com/index.php?title=Cunningham_function&amp;amp;diff=266536&amp;amp;oldid=25518&quot;&gt;Show changes&lt;/a&gt;</summary>
		<author><name>en&gt;Rjwilmsi</name></author>
	</entry>
	<entry>
		<id>https://en.formulasearchengine.com/index.php?title=Cunningham_function&amp;diff=25518&amp;oldid=prev</id>
		<title>en&gt;CitationCleanerBot: Various citation &amp; identifier cleanup, plus AWB genfixes. Report errors and suggestions at User talk:CitationCleanerBot. using AWB</title>
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		<updated>2011-09-10T21:35:36Z</updated>

		<summary type="html">&lt;p&gt;Various citation &amp;amp; identifier cleanup, plus AWB genfixes. Report errors and suggestions at &lt;a href=&quot;/index.php?title=User_talk:CitationCleanerBot&amp;amp;action=edit&amp;amp;redlink=1&quot; class=&quot;new&quot; title=&quot;User talk:CitationCleanerBot (page does not exist)&quot;&gt;User talk:CitationCleanerBot&lt;/a&gt;. using &lt;a href=&quot;/index.php?title=Testwiki:AWB&amp;amp;action=edit&amp;amp;redlink=1&quot; class=&quot;new&quot; title=&quot;Testwiki:AWB (page does not exist)&quot;&gt;AWB&lt;/a&gt;&lt;/p&gt;
&lt;p&gt;&lt;b&gt;New page&lt;/b&gt;&lt;/p&gt;&lt;div&gt;{{chembox&lt;br /&gt;
| Watchedfields = changed&lt;br /&gt;
| verifiedrevid = 439552228&lt;br /&gt;
| ImageFile1 = Structure of Ruthenium (III) acac.png&lt;br /&gt;
| ImageSize1 = 180px&lt;br /&gt;
| ImageFile2 = &lt;br /&gt;
| ImageSize2 = &lt;br /&gt;
| IUPACName = Tris(acetylacetonato)Ruthenium (III)&lt;br /&gt;
| OtherNames = Ru(acac)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;; Ruthenium (III) 2,4-Pentanedionate; Ruthenium (III) acetylacetonato, 2,4-pentanedione ruthenium (III)&lt;br /&gt;
| Section1 = {{Chembox Identifiers&lt;br /&gt;
| Abbreviations = &lt;br /&gt;
| CASNo = 14284-93-6&lt;br /&gt;
|  CASNo_Ref = {{cascite|correct|??}}&lt;br /&gt;
| EINECS = &lt;br /&gt;
| PubChem = 16057901&lt;br /&gt;
| SMILES = &lt;br /&gt;
| InChI = 1S/3C5H8O2.Ru/c3*1-4(6)3-5(2)7;/h3*3H2,1-2H3;&lt;br /&gt;
| RTECS = &lt;br /&gt;
| MeSHName =&lt;br /&gt;
| ChEBI_Ref = {{ebicite|correct|EBI}}&lt;br /&gt;
| ChEBI =&lt;br /&gt;
| KEGG_Ref = {{keggcite|correct|kegg}}&lt;br /&gt;
| KEGG = &lt;br /&gt;
| SMILES = CC(=O)CC(=O)C.CC(=O)CC(=O)C.CC(=O)CC(=O)C.[Ru]&lt;br /&gt;
| ATCCode_prefix = &lt;br /&gt;
| ATCCode_suffix = &lt;br /&gt;
| ATC_Supplemental =}}&lt;br /&gt;
| Section2 = {{Chembox Properties&lt;br /&gt;
| Formula = (C&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;7&amp;lt;/sub&amp;gt;O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;Ru&lt;br /&gt;
| MolarMass = 398.39 g/mol&lt;br /&gt;
| Appearance = Dark Violet Solid&lt;br /&gt;
| Density = 1.54 g/cm&amp;lt;sup&amp;gt;3&amp;lt;/sup&amp;gt;&amp;lt;ref name=ActaCryst&amp;gt;{{cite journal&lt;br /&gt;
| title = Crystal and molecular structure of tris(acetylacetonato)ruthenium(III) &lt;br /&gt;
| author = Chao, G.&lt;br /&gt;
| journal =  Acta Crystallographica B&lt;br /&gt;
| year = 1973&lt;br /&gt;
| volume = 29 &lt;br /&gt;
| issue =  12&lt;br /&gt;
| pages = 2845&lt;br /&gt;
| doi = 10.1107/S0567740873007636&lt;br /&gt;
| last2 = Sime&lt;br /&gt;
| first2 = R. L.&lt;br /&gt;
| last3 = Sime&lt;br /&gt;
| first3 = R. J.&lt;br /&gt;
}}&amp;lt;/ref&amp;gt;&lt;br /&gt;
| MeltingPt = 260 °C&lt;br /&gt;
| Melting_notes =&lt;br /&gt;
| BoilingPt = &lt;br /&gt;
| Boiling_notes = &lt;br /&gt;
| Solubility = insoluble in water&lt;br /&gt;
| SolubleOther = soluble in most organic solvents&lt;br /&gt;
| Solvent = &lt;br /&gt;
| pKa = &lt;br /&gt;
| pKb = }}&lt;br /&gt;
| Section7 = {{Chembox Hazards&lt;br /&gt;
| EUClass = &lt;br /&gt;
| EUIndex = &lt;br /&gt;
| MainHazards = &lt;br /&gt;
| NFPA-H = &lt;br /&gt;
| NFPA-F = &lt;br /&gt;
| NFPA-R = &lt;br /&gt;
| NFPA-O = &lt;br /&gt;
| RPhrases = {{R36}}, {{R37}}, {{R38}}&lt;br /&gt;
| SPhrases = {{S26}}, {{S36}}&lt;br /&gt;
| RSPhrases =&lt;br /&gt;
| FlashPt = &lt;br /&gt;
| Autoignition = &lt;br /&gt;
| ExploLimits = &lt;br /&gt;
| PEL = }}&lt;br /&gt;
}}&lt;br /&gt;
&amp;#039;&amp;#039;&amp;#039;Ruthenium(III) acetylacetonate&amp;#039;&amp;#039;&amp;#039; is a [[coordination complex]] with the formula [[Ruthenium|Ru]](O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;C&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;7&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;.  O&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;C&amp;lt;sub&amp;gt;5&amp;lt;/sub&amp;gt;H&amp;lt;sub&amp;gt;7&amp;lt;/sub&amp;gt;)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; is the ligand called [[acetylacetonate]]. This compound exists as a dark violet solid that is soluble in most organic solvents.&amp;lt;ref&amp;gt;R.C. Mehrotra, R. Bohra, and D.P. Gaur &amp;quot;Metal β-Diketonates and Allied Derivatives&amp;quot;, 1st ed.; Academic Press inc.: New York, 1978. ISBN 0-12-488150-5.&amp;lt;/ref&amp;gt; It is used as a precursor to other compounds of ruthenium.&lt;br /&gt;
&lt;br /&gt;
==Preparation==&lt;br /&gt;
In 1914 tris(acetylacetonato)ruthenium (III) was first prepared by the reaction of [[ruthenium(III) chloride]] and [[acetylacetone]] in the presence of [[potassium bicarbonate]].&amp;lt;ref&amp;gt;{{cite journal&lt;br /&gt;
| title = Systematic chemical investigations: ruthenium, rhodium, palladium &lt;br /&gt;
| author = Barbieri, G. A.&lt;br /&gt;
| journal =  Atti accad, Lincei &lt;br /&gt;
| year = 1914&lt;br /&gt;
| volume = 23&lt;br /&gt;
| issue = 1 &lt;br /&gt;
| pages = 334–40&lt;br /&gt;
| doi = &lt;br /&gt;
}}&amp;lt;/ref&amp;gt;  Since then, alternative synthetic routes have been examined, but the original procedure remains useful with minor variations:&amp;lt;ref&amp;gt;{{cite journal&lt;br /&gt;
| title = Improved synthesis and reactivity of tris(acetylacetonato)ruthenium(III)&lt;br /&gt;
| author = Gupta, A.&lt;br /&gt;
| journal =  Indian journal of chemistry. Section A, Inorganic, bio-inorganic, physical, theoretical &amp;amp; analytical chemistry &lt;br /&gt;
| year = 2000&lt;br /&gt;
| volume = 39A&lt;br /&gt;
| issue = 4&lt;br /&gt;
| pages = 457&lt;br /&gt;
| issn = 0376-4710 &lt;br /&gt;
}}&amp;lt;/ref&amp;gt;&lt;br /&gt;
:RuCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;•3H&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;O + MeCOCH&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;COMe   →   Ru(acac)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;  +  3 HCl  +  3 H&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;O&lt;br /&gt;
&lt;br /&gt;
==Structure and properties==&lt;br /&gt;
This compound has idealized D&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; symmetry. Six oxygen atoms surround the central ruthenium atom in an octahedral arrangement. The average Ru-O bond length in Ru(acac)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; is 2.00 Å.&amp;lt;ref name=ActaCryst/&amp;gt; Because Ru(acac)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; is low spin, there is one unpaired &amp;#039;&amp;#039;d&amp;#039;&amp;#039; electron, causing this compound to be paramagnetic.  Ru(acac)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; has a magnetic susceptibility, χ&amp;lt;sub&amp;gt;M&amp;lt;/sub&amp;gt;, of 3.032×10&amp;lt;sup&amp;gt;−6&amp;lt;/sup&amp;gt; cm&amp;lt;sup&amp;gt;3&amp;lt;/sup&amp;gt;/mol with an effective magnetic moment, μ&amp;lt;sub&amp;gt;eff&amp;lt;/sub&amp;gt;, of 1.66 μ&amp;lt;sub&amp;gt;B&amp;lt;/sub&amp;gt;.&amp;lt;ref&amp;gt;{{cite journal&lt;br /&gt;
| title = The absorption spectra and magnetic properties of the chelated compounds of Ru(III) with β-diketones &lt;br /&gt;
| author = Grobelny, R.&lt;br /&gt;
| journal =  Journal of inorganic and nuclear chemistry&lt;br /&gt;
| year = 1966&lt;br /&gt;
| volume = 28 &lt;br /&gt;
| issue = 11 &lt;br /&gt;
| pages = 2715&lt;br /&gt;
| doi = 10.1016/0022-1902(66)80398-6&lt;br /&gt;
}}&amp;lt;/ref&amp;gt;  As a solution in [[dimethylformamide|DMF]], the compound oxidizes at 0.593 and reduces at -1.223 V vs the [[ferrocene]]/[[ferrocenium]] couple.&amp;lt;ref&amp;gt;{{cite journal&lt;br /&gt;
| title = Alkyl Substituent Effects in the Redox Thermochemistry of Coordination Compounds: Oxidation and Reduction Energetics for Ruthenium Tris(β-diketonate) Complexes in Solution and the Gas Phase  &lt;br /&gt;
| author = Paul Sharpe, N. George Alameddin, David E. Richardson&lt;br /&gt;
| journal =  Journal of the American Chemical Society&lt;br /&gt;
| year = 1994&lt;br /&gt;
| volume = 116&lt;br /&gt;
| issue = 24&lt;br /&gt;
| pages = 11098–11108&lt;br /&gt;
| doi = 10.1021/ja00103a027&lt;br /&gt;
}}&amp;lt;/ref&amp;gt;&lt;br /&gt;
&lt;br /&gt;
Reduction of Ru(acac)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; in the presence of [[alkenes]] affords the related diolefin complexes. Typically, such reactions are conducted with [[zinc]] [[amalgam (chemistry)|amalgam]] in moist [[tetrahydrofuran]]:&amp;lt;ref&amp;gt;{{cite journal&lt;br /&gt;
| title = The fragment bis(acetylacetonato)ruthenium: a meeting-point of coordination and organometallic chemistry  &lt;br /&gt;
| author = Bennett, M. A.&lt;br /&gt;
| journal =  Journal of Organometallic Chemistry&lt;br /&gt;
| year = 2004&lt;br /&gt;
| volume = 689 &lt;br /&gt;
| issue = 24 &lt;br /&gt;
| pages = 4463&lt;br /&gt;
| doi = 10.1016/j.jorganchem.2004.07.027&lt;br /&gt;
| last2 = Byrnes&lt;br /&gt;
| first2 = Matthew J.&lt;br /&gt;
| last3 = Kováčik&lt;br /&gt;
| first3 = Ivan&lt;br /&gt;
}}&amp;lt;/ref&amp;gt; &lt;br /&gt;
:2 Ru(acac)&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt;  +  4 alkene  +  Zn  →   2 Ru(acac)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;(alkene)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;  +  Zn(acac)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;&lt;br /&gt;
The resulting compounds are rare examples of metal-alkene complexes that reversibly sustain oxidation: &lt;br /&gt;
:Ru(acac)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;(alkene)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;  &amp;lt;math&amp;gt;\overrightarrow{\leftarrow}&amp;lt;/math&amp;gt;   [Ru(acac)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;(alkene)&amp;lt;sub&amp;gt;2&amp;lt;/sub&amp;gt;]&amp;lt;sup&amp;gt;+&amp;lt;/sup&amp;gt;  +  e&amp;lt;sup&amp;gt;-&amp;lt;/sup&amp;gt;&lt;br /&gt;
&lt;br /&gt;
==References==&lt;br /&gt;
{{reflist}}&lt;br /&gt;
&lt;br /&gt;
[[Category:Ruthenium compounds]]&lt;br /&gt;
[[Category:Acetylacetonate complexes]]&lt;/div&gt;</summary>
		<author><name>en&gt;CitationCleanerBot</name></author>
	</entry>
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