| Revision as of 19:58, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 468314978 of page Acetylenediol for the Chem/Drugbox validation project (updated: ''). |
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{{Use dmy dates|date=May 2023}} |
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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 = 453634206 |
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|Watchedfields = changed |
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| Name = Acetylenediol |
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|verifiedrevid = 477240466 |
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| Reference = |
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| ImageFile = Ethyne-1,2-diol.svg |
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|Name = Acetylenediol |
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|ImageFile = Ethyne-1,2-diol.svg |
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| ImageSize = 230px |
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|ImageSize = 230px |
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| ImageName = Displayed formula of acetylenediol |
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|ImageName = Displayed formula of acetylenediol |
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| ImageFile1 = Acetylenediol-3D-balls.png |
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|ImageFile1 = Acetylenediol-3D-balls.png |
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| ImageSize1 = 220px |
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|ImageSize1 = 220px |
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| ImageName1 = Ball-and-stick model of acetylenediol |
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|ImageName1 = Ball-and-stick model of acetylenediol |
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|PIN = Ethynediol |
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| IUPACName = |
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| OtherNames = ethynediol, dihydroxyacetylene |
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|OtherNames = Dihydroxyacetylene |
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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 = 8117727 |
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|ChemSpiderID = 8117727 |
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| InChI = 1/C2H2O2/c3-1-2-4/h3-4H |
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|InChI = 1/C2H2O2/c3-1-2-4/h3-4H |
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| InChIKey = ZUQAPLKKNAQJAU-UHFFFAOYAS |
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|InChIKey = ZUQAPLKKNAQJAU-UHFFFAOYAS |
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| SMILES1 = OC#CO |
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|SMILES1 = OC#CO |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C2H2O2/c3-1-2-4/h3-4H |
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|StdInChI = 1S/C2H2O2/c3-1-2-4/h3-4H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZUQAPLKKNAQJAU-UHFFFAOYSA-N |
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|StdInChIKey = ZUQAPLKKNAQJAU-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = |
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|CASNo = 16005-17-7 |
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| PubChem = 9942115 |
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|PubChem = 9942115 |
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| SMILES = C(#CO)O }} |
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|SMILES = C(#CO)O}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=2 | H=2 | O=2 |
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| Formula = C<sub>2</sub>H<sub>2</sub>O<sub>2</sub> |
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| MolarMass = 58,07 g/mol |
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|MolarMass = 58.07 g/mol |
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|BoilingPt = decomposes}} |
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| Density = |
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| MeltingPt = |
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| BoilingPt = dec. }} |
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| Section7 = {{Chembox Hazards |
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| NFPA-H = |
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'''Acetylenediol''', or '''ethynediol''', is a ] with formula HO−C≡C−OH (an ]). It is the ] of ]. Acetylenediol is unstable in the condensed phase, although its ] ] (CHO)<sub>2</sub> is well known. |
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==Detection== |
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Acetylenediol was first observed in the gas-phase by ].<ref name="terlouw">{{cite journal|first1=Johan K.|last1=Terlouw|first2=Peter C.|last2=Burgers|first3=Ben L. M.|last3=van Baar|first4=Thomas|last4=Weiske|author5-link=Helmut Schwarz|first5=Helmut|last5=Schwarz|date=1986|title=The Formation in the Gas Phase of HO–CC–OH, H<sub>2</sub>N–CC–NH<sub>2</sub>, H<sub>2</sub>N–CC–OH and Related Compounds by Selective Reduction of Their Cations|journal=CHIMIA|volume=40|pages=357–359|url=http://www.chem.tu-berlin.de/Thomas.Weiske/Publikationen/Publikation0017/Text0017.HTML|accessdate=2009-08-01}}</ref> The compound was later obtained by ] of ] in a ] at {{convert|10|K|C|0}}.<ref name="maier95">{{cite journal|first1=Günther|last1=Maier|first2=Christine|last2=Rohr|date=1995|title=Ethynediol: Photochemical generation and matrix-spectroscopic identification|journal=Liebigs Annalen|volume=1996|issue=3|pages=307–309|doi=10.1002/jlac.199619960303 }}</ref> Recently, this molecule was synthesized in interstellar ice analogs composed of ] (CO) and ] (H<sub>2</sub>O) upon exposure to energetic electrons and detected upon sublimation by isomer-selective photoionization ].<ref>{{cite journal |last1=Wang |first1=Jia |last2=Turner |first2=Andrew M. |last3=Marks |first3=Joshua H. |last4=Zhang |first4=Chaojiang |last5=Kleimeier |first5=N. Fabian |last6=Bergantini |first6=Alexandre |last7=Singh |first7=Santosh K. |last8=Fortenberry |first8=Ryan C. |last9=Kaiser |first9=Ralf I. |title=Preparation of Acetylenediol (HOCCOH) and Glyoxal (HCOCHO) in Interstellar Analog Ices of Carbon Monoxide and Water |journal=The Astrophysical Journal |date=1 June 2024 |volume=967 |issue=2 |pages=79 |doi=10.3847/1538-4357/ad3c3e|doi-access=free }}</ref> |
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==Derivatives== |
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===Alkoxide derivatives=== |
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Like the diol, most simple ether derivatives are labile. ] is however a distillable liquid. |
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===Acetylenediolate salts=== |
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Salts of the '''acetylenediolate''' ('''ethynediolate''') dianion <sup>−</sup>O−C≡C−O<sup>−</sup> are known. They are not however prepared from ethynediol, but by the reduction of ]. Potassium acetylenediolate (K<sub>2</sub>C<sub>2</sub>O<sub>2</sub>) was first obtained by ] in 1834, from the reaction of ] with metallic ];<ref name="liebig">Justus Liebig (1834), Annalen der Chemie und Pharmacie, volume 11, p. 182. Cited by Raymond N. Vrtis et al. (1988), JACS p. 7564.</ref> but for a long time the product was assumed to be "potassium carbonyl" (KCO). Over the next 130 years were described the "carbonyls" of ] (Johannis, 1893), ] (Gunz and Mentrel, 1903), ] (Roederer, 1906), and ], ], and ] (Pearson, 1933).<ref name="pearson">T. G. Pearson (1933), ''Carbonyls of Lithium, Rubidium and Caesium''. Nature, volume 131, pp. 166–167 (4 February 1933). {{doi|10.1038/131166b0}}</ref> The reaction was eventually shown to yield a mixture of the potassium acetylenediolate {{chem|K|2|C|2|O|2}} and potassium benzenehexolate {{chem|K|6|C|6|O|6}}.<ref name="wbuechIV">Werner Büchner, E. Weiss (1964) ''Zur Kenntnis der sogenannten «Alkalicarbonyle» IV Über die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid. Helvetica Chimica Acta'', Volume 47 Issue 6, Pages 1415–1423.{{doi|10.1002/hlca.19640470604}}</ref> |
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The structure of these salts was clarified only in 1963 by Büchner and Weiss.<ref name="webuech">Werner Büchner, E. Weiss (1963) ''Zur Kenntnis der sogenannten «Alkalicarbonyle» I Die Kristallstruktur des Kalium-acetylendiolats, KOC≡COK''. Helvetica Chimica Acta, Volume 46 Issue 4, Pages 1121–1127. {{doi|10.1002/hlca.19630460404}}<!--Abstract: The structure of the yellow «potassium carbonyl», obtained from CO and K in liquid ammonia, has been shown to be potassium acetylenediolate, KOC≡COK. From X-ray powder-diagrams a tetragonal cell containing two KOC≡COK units with a = 3.93, Å, c = 12.75 Å (space group I 4/mmm) has been derived. The KOC≡COK units are arranged parallel to the c-axis with the following internuclear distances: K—0: 2.67 and 2.78 Å; K—K: 3.65 Å; C—0 : 1.28 Å; C—C: 1.21 Å.--></ref><ref name="webuechII">E. Weiss, Werner Büchner (1963), ''Zur Kenntnis der sogenannten Alkalicarbonyle. II. Die Kristallstrukturen des Rubidium- und Caesium-acetylendiolats, RbOC≡CORb und CsOC≡COCs.'' Zeitschrift für anorganische und allgemeine Chemie, Volume 330 Issue 5-6, Pages 251–258. {{doi|10.1002/zaac.19643300504}}</ref> |
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Acetylenediolates can also be prepared by the rapid reaction of CO and a solution of the corresponding metal in liquid ] at low temperature.<ref name="pearson"/> Potassium acetylenediolate is a pale yellow solid that reacts explosively with air, halogens, halogenated hydrocarbons, alcohols, water, and any substance which possesses an acidic hydrogen.<ref name="taylor">Charles Kenneth Taylor (1982), ''The Chemical Behavior of the Alkali Metal Acetylenediolates''. Thesis, Pennsylvania State University; also Technical Memo A642321, Penn State University Park Applied Research Lab. 227 pages.</ref> |
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===Coordination complexes=== |
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Acetylenediol can form ]s, such as <sup>+</sup>Cl<sup>−</sup> where dmpe is ].<ref name="vrtis">Raymond N. Vrtis, Ch. Pulla Rao, Simon G. Bott, and Stephen J. Lippard (1988), ''Synthesis and Stabilization of Tantalum-Coordinated Dihydroxyacetylene from Two Reductively Coupled Carbon Monoxide Ligands'' J. Am. Chem. Soc., volume 110 issue 22, pp. 7564–7566. {{doi|10.1021/ja00230a062}}</ref> |
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Acetylenediolate and related anions such as ] {{chem|C|3|O|3|2-}} and ] {{chem|C|4|O|4|2-}} have been obtained from carbon monoxide under mild conditions by reductive coupling of CO ligands in ].<ref name=frey>Alistair S. Frey, F. Geoffrey N. Cloke, Peter B. Hitchcock (2008), ''Mechanistic Studies on the Reductive Cyclooligomerisation of CO by U(III) Mixed Sandwich Complexes; the Molecular Structure of <sub>2</sub>(μ-η<sup>1</sup>:η<sup>1</sup>-C<sub>2</sub>O<sub>2</sub>)'' Journal of the American Chemical Society, volume 130, issue 42, pages 13816–13817. {{doi|10.1021/ja8059792}}</ref> |
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==See also== |
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==References== |
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{{reflist}} |
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