[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/all2en\/wiki32\/ethynediol-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/all2en\/wiki32\/ethynediol-wikipedia\/","headline":"Ethynediol \u2014 Wikipedia","name":"Ethynediol \u2014 Wikipedia","description":"A wikipedia article, free l’encyclop\u00e9i. \u00c9thynediol Identification UICPA name \u00e9thyne-1,2-diol Synonyms acetyl\u00e8nediol, dihydroxyacetylene N O CAS 16005-17-7 Pubchem 9942115 SMILES","datePublished":"2020-12-27","dateModified":"2020-12-27","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/all2en\/wiki32\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/all2en\/wiki32\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/44a4cee54c4c053e967fe3e7d054edd4?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/44a4cee54c4c053e967fe3e7d054edd4?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/6\/6d\/Ethyne-1%2C2-diol.svg\/langfr-180px-Ethyne-1%2C2-diol.svg.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/6\/6d\/Ethyne-1%2C2-diol.svg\/langfr-180px-Ethyne-1%2C2-diol.svg.png","height":"27","width":"180"},"url":"https:\/\/wiki.edu.vn\/all2en\/wiki32\/ethynediol-wikipedia\/","wordCount":2314,"articleBody":"A wikipedia article, free l’encyclop\u00e9i. \u00c9thynediol  Identification UICPA name \u00e9thyne-1,2-diol  Synonyms acetyl\u00e8nediol, dihydroxyacetylene N O CAS 16005-17-7  Pubchem 9942115  SMILES  Inches Inches:  3D view  Inchi = 1\/C2H2O2\/C3-1-2-4\/H3-4H Chemicals Formula C 2 H 2 O 2  [Isomers] Molar mass [ first ] 58.036 1 \u00b1 0.002 3 g\/mol C\u00a041,39\u00a0%,  H\u00a03,47\u00a0%,  O\u00a055,14\u00a0%,  Physical properties T\u00b0 boiling Decomp. IS units and CNTP , unless otherwise stated. modifier  L’ \u00e9thynediol or acetyl\u00e8nediol is an organic compound of semi-developed formula Ho\u2013C\u2261c-oh. It is the dialcool of ethyne. Ethynediol is unstable in the condensed phase although its tautomer, ethanedial (glyoxal), o = ch – = o is well known.   Ethynediol was observed for the first time in 1986 by J. K. Terlouw et al. in the gas phase by mass spectrometry [ 2 ] . In 1995, this compound was obtained by G\u00fcnther Maier and Christine Rohr by photolsing square acid in a solid Argon matrix at 10 k ( \u2212263,2 \u00b0C ) [ 3 ] . Alkoxyde [ modifier | Modifier and code ] Although Diol has only ephemeral existence in condensed form, salts and derivatives of its combined base, the ethynedoiola Dianion (acetylenedoiola), (oc\u2261co) 2\u2212 are well known. These alkoxides are formally derived from Ethynediol by the loss of two protons but in fact, they are not generated in this way but rather by reducing carbon monoxide. Potassium ethynedoiola, k 2 C 2 O 2 was first obtained by Justus von Liebig in 1834, by reaction of carbon monoxide with metal potassium [ 4 ] . However, for a very long time, the compound resulting from this reaction was seen as “carbonyl potassium”. During the following 130 years, many other “carbonyls” were described: sodium (Johannis, 1893), Baryum (Gunz and Mentrel, 1903), Stontium (Roederer, 1906) and Lithium, Rubidium and Cesium (Pearson, 1933) [ 5 ] . The real structure of these salts was only clarified in 1963 by Werner B\u00fcchner and E. Weiss [ 6 ] , [ 7 ] . Finally, in 1964, they show that the reaction produced a mixture of potassium ethynedoiola, k 2 C 2 O 2 And of Benz\u00e8nehexolate of potassium, k 6 C 6 O 6 [ 8 ] . Ethynedoiolates can also be prepared by the reaction -rapide- of CO on a solution of the metal corresponding in the liquid ammonia at low temperature [ 5 ] . Potassium ethynediolate is a solid pale yellow that reacts explosively with air, halogens, halogenated hydrocarbons, alcohols, water and any substance that has one or more acid hydrogen atoms [ 9 ] . Ether [ modifier | Modifier and code ] Although still practically not derived from ethynediol, a large number of stable ethynedoiolate compounds are known. Examples include diisopropoxyethyne diethers ((ch 3 ) 2 CH) \u2013O – C\u2261C – O – (CH (CH (CH 3 ) 2 ) et di-tert-butoxy\u00e9thyne, ((ch 3 ) 3 C)\u2013O\u2013C\u2261C\u2013O\u2013(C(CH 3 ) 3 ) [ ten ] . Coordination complex [ modifier | Modifier and code ] The [Tah (hoc\u2261coh) complex (DMPE) 2 Cl] + Cl – (DMPE = bis (1,2-dimethylphosphino) ethane) is a derivative of ethynediol [ 11 ] . Ethynedoiolates and similar anions such as deltates, c 3 O 3 2\u2212 and squars, c 4 O 4 2\u2212 were obtained from carbon monoxide under soft conditions by reducing coupling of CO ligands in organo-uranie chemistry [ twelfth ] . \u2191 Molar mass calculated after ‘ Atomic weights of the elements 2007 \u00bb , on www.chem.qmul.ac.uk .  \u2191 Johan K. Terlouw, Peter C. Burgers, Ben L. M. van Baar, Thomas Weiske and Helmut Schwarz, The Formation in the Gas Phase of HO-CC-OH, H2N-CC-NH2, H2N-CC-OH and related Compounds by Selective Reduction of their Cations , Chemistry , 1986, vol. 40, pp. 357\u2013359. Online version .  \u2191 G\u00fcnther Maier, Christine Rohr, Ethynediol: Photochemical generation and matrix-spectroscopic identification.  Liebigs Ann. , 1995, vol. 1996 (3), pp. 307\u2013309. DOI\u00a0 10.1002\/JLAC.15719960304 .  \u2191 Justus Liebig (1834), Annals of Chemistry and Pharmacie, Volume 11, p. 182. Cited by Raymond N. Vrtis et al (1988), J. Am. Chem. Soc. p. 7564.  \u2191 a et b T. G. Pearson, Carbonyls of Lithium, Rubidium and Cesium , Nature , 1933, vol. 131, pp. 166\u2013167. DOI\u00a0 10.1038\/131166b0  \u2191 Werner B\u00fcchner, E. Weiss, To the knowledge of the so-called \u201calkalicarbonyle\u201d I The crystal structure of the potassium-acetyl diolate, koc\u2261cok , Helv. Bird. Acta , 1963, vol. 46 (4), pp. 1121\u20131127. DOI\u00a0 10.1002\/HLCA.19630460404 .  \u2191 E. Weiss, Werner B\u00fcchner, To the knowledge of the so -called alkalicarbonyl. II. The crystal structures of the rubidium and cesium acetyl diolate, rboc\u2261corb and CSoc\u2261cocs. , Z. Anorg. Allg. Chem. , 1963, vol. 330 (5-6), pp. 251\u2013258. DOI\u00a0 10.1002 \/ ZAC.1964300504 .  \u2191 Werner B\u00fcchner, E. Weiss, To the knowledge of the so -called \u201calkalicarbonyle\u201d IV [1] about the reaction of melted potassium with carbon monoxide , Helv. Bird. Acta , 1964, vol. 47 (6), pp. 1415\u20131423. DOI\u00a0 10.1002\/HLCA.19640470604 .  \u2191 Charles Kenneth Taylor, The Chemical Behavior of the Alkali Metal Acetylenediolates , Thesis, 1982, Pennsylvania State University, aussi Technical Memo A642321, Penn State University Park Applied Research Lab., 227 pages.  \u2191 Anna Bou, Miquel A. Peric\u00e0s and F\u00e9lix Serratosa (1981), Diisopropoxy- and di-tert-butoxyethyne\u00a0: Stable acetylene diethers . Tetrahedron , Volume 37, Issue 7, Pages 1441-1449. DOI\u00a0 10.1016\/S0040-4020(01)92464-0  \u2191 Raymond N. vrtis, ch. Pulla rao, simon g. bott and stephen j. lippard, Synthesis and Stabilization of Tantalum-Coordinated Dihydroxyacetylene from Two Reductively Coupled Carbon Monoxide Ligands , J. Am. Chem. Soc. , 1988, vol. 110 (22), pp. 7564\u20137566. DOI\u00a0 10.1021\/ja00230a062 .  \u2191 Alistair S. Frey, F. Geoffrey N. Cloke, Peter B. Hitchcock, Mechanistic Studies on the Reductive Cyclooligomerisation of CO by U(III) Mixed Sandwich Complexes; the Molecular Structure of [(U(\u03b7-C 8 H 6 {SI’PR 3 -1,4} 2 ) (\u03b7-CP * )] 2 (non first :the first -C 2 O 2 ) , J. Am. Chem. Soc. , 2008, vol. 130 (42), pp. 13816\u201313817. DOI\u00a0 10.1021\/ja8059792    "},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/all2en\/wiki32\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/all2en\/wiki32\/ethynediol-wikipedia\/#breadcrumbitem","name":"Ethynediol \u2014 Wikipedia"}}]}]