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{{Use dmy dates|date=May 2023}}
{{chembox {{chembox
|Verifiedfields = changed
⚫ | verifiedrevid = 453634206
|Watchedfields = changed
| Name = Acetylenediol
⚫ |verifiedrevid = 477240466
| Reference =
| ImageFile = Ethyne-1,2-diol.svg |Name = Acetylenediol
|ImageFile = Ethyne-1,2-diol.svg
| ImageSize = 230px |ImageSize = 230px
| ImageName = Displayed formula of acetylenediol |ImageName = Displayed formula of acetylenediol
| ImageFile1 = Acetylenediol-3D-balls.png |ImageFile1 = Acetylenediol-3D-balls.png
| ImageSize1 = 220px |ImageSize1 = 220px
| ImageName1 = Ball-and-stick model of acetylenediol |ImageName1 = Ball-and-stick model of acetylenediol
|PIN = Ethynediol
| IUPACName =
| OtherNames = ethynediol, dihydroxyacetylene |OtherNames = Dihydroxyacetylene
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8117727 |ChemSpiderID = 8117727
| InChI = 1/C2H2O2/c3-1-2-4/h3-4H |InChI = 1/C2H2O2/c3-1-2-4/h3-4H
| InChIKey = ZUQAPLKKNAQJAU-UHFFFAOYAS |InChIKey = ZUQAPLKKNAQJAU-UHFFFAOYAS
| SMILES1 = OC#CO |SMILES1 = OC#CO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H2O2/c3-1-2-4/h3-4H |StdInChI = 1S/C2H2O2/c3-1-2-4/h3-4H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZUQAPLKKNAQJAU-UHFFFAOYSA-N |StdInChIKey = ZUQAPLKKNAQJAU-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}} |CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = |CASNo = 16005-17-7
| PubChem = 9942115 |PubChem = 9942115
| SMILES = C(#CO)O }} |SMILES = C(#CO)O}}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
|C=2 | H=2 | O=2
| Formula = C<sub>2</sub>H<sub>2</sub>O<sub>2</sub>
| MolarMass = 58,07 g/mol |MolarMass = 58.07 g/mol
⚫ |BoilingPt = decomposes}}
| Density =
| MeltingPt =
⚫ | BoilingPt = dec. }}
| Section7 = {{Chembox Hazards
| NFPA-H =
| NFPA-F =
| NFPA-R = }}
}} }}


'''Acetylenediol''', or '''ethynediol''', is a ] with formula HO-C&equiv;C-OH. It is the ] of ]. Acetylenediol is unstable in the condensed phase, although its ] ] H(C=O)<sub>2</sub>H is well known. '''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.


==Detection== ==Detection==
Acetylenediol was first observed in 1986 by ] and others in gas-phase by mass spectrometry.<ref name="terlouw">Johan K. Terlouw, Peter C. Burgers, Ben L. M. van Baar, Thomas Weiske, and ] (1986), ''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'', Chimia, volume 40, page 357–359. accessed on 2009-08-01.</ref> In 1995, the compound was obtained by Günther Maier and Christine Rohr through photolysis of ] in a solid ] ] at {{convert|10|K|C}}.<ref name="maier95">Günther Maier, Christine Rohr (1995), ''Ethynediol: Photochemical generation and matrix-spectroscopic identification.'' Liebigs Annalen, Volume 1996 Issue 3, Pages 307–309. {{doi|10.1002/jlac.15719960304}} </ref> 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>


==Derivatives== ==Derivatives==

===Alkoxide derivatives=== ===Alkoxide derivatives===
Like the diol, most simple ether derivatives are labile. ] is however a distillable liquid.
Although the diol has only fleeting existence in concentrated form, salts of the '''acetylenediolate''' ('''ethynediolate''') dianion (O-C&equiv;C-O)<sup>2&minus;</sup> are well known. These ]s (specifically, ]s) are formally derived from ethynediol by loss of two ], but they are not normally generated in that way.


===Acetylenediolate salts===
The typical synthesis route for these salts is the reduction of carbon monoxide. 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 (04 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 ] {{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> 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>


The true structure of these salts was clarified only in 1963 by ] and ].<ref name="webuech">Werner Büchner, E. Weiss (1963) ''Zur Kenntnis der sogenannten «Alkalicarbonyle» I Die Kristallstruktur des Kalium-acetylendiolats, KOC&equiv;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&equiv;COK. From X-ray powder-diagrams a tetragonal cell containing two KOC&equiv;COK units with a = 3.93, Å, c = 12.75 Å (space group I 4/mmm) has been derived. The KOC&equiv;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&equiv;CORb und CsOC&equiv;COCs.'' Zeitschrift für anorganische und allgemeine Chemie, Volume 330 Issue 5-6, Pages 251–258. {{doi|10.1002/zaac.19643300504}}</ref> 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>


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> 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>


===Coordination complexes=== ===Coordination complexes===
Acetylenediol can form ]s, such as <sup>+</sup>Cl<sup>&minus;</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> Acetylenediol can form ]s, such as <sup>+</sup>Cl<sup>&minus;</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>


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> 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>

==Other derivatives==
Although again not derived from acetylenediol, a variety of structurally related compounds are known. Examples include the di]s ] ((CH<sub>3</sub>)<sub>2</sub>CH)-O-C&equiv;C-O-(CH(CH<sub>3</sub>)<sub>2</sub>) and ] ((CH<sub>3</sub>)<sub>3</sub>C)-O-C&equiv;C-O-(C(CH<sub>3</sub>)<sub>3</sub>).<ref name="Bou">Anna Bou, Miquel A. Pericàs and Félix Serratosa (1981), ''Diisopropoxy- and di-tert-butoxyethyne : Stable acetylene diethers''. Tetrahedron, Volume 37, Issue 7, Pages 1441-1449. {{doi|10.1016/S0040-4020(01)92464-0}}</ref>


==See also== ==See also==
*] *]
*]
*] *]


==References== ==References==
{{reflist|2}} {{reflist}}

⚫ ]


] ]
⚫ ]
]
]

Latest revision as of 05:17, 25 May 2024

Acetylenediol
Displayed formula of acetylenediol
Ball-and-stick model of acetylenediol
Names
Preferred IUPAC name Ethynediol
Other names Dihydroxyacetylene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H2O2/c3-1-2-4/h3-4HKey: ZUQAPLKKNAQJAU-UHFFFAOYSA-N
  • InChI=1/C2H2O2/c3-1-2-4/h3-4HKey: ZUQAPLKKNAQJAU-UHFFFAOYAS
SMILES
  • C(#CO)O
  • OC#CO
Properties
Chemical formula C2H2O2
Molar mass 58.07 g/mol
Boiling point decomposes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Acetylenediol, or ethynediol, is a chemical substance with formula HO−C≡C−OH (an ynol). It is the diol of acetylene. Acetylenediol is unstable in the condensed phase, although its tautomer glyoxal (CHO)2 is well known.

Detection

Acetylenediol was first observed in the gas-phase by mass spectrometry. The compound was later obtained by photolysis of squaric acid in a solid argon matrix at 10 K (−263 °C). Recently, this molecule was synthesized in interstellar ice analogs composed of carbon monoxide (CO) and water (H2O) upon exposure to energetic electrons and detected upon sublimation by isomer-selective photoionization reflectron time-of-flight mass spectrometry.

Derivatives

Alkoxide derivatives

Like the diol, most simple ether derivatives are labile. Di-tert-butoxyacetylene is however a distillable liquid.

Acetylenediolate salts

Salts of the acetylenediolate (ethynediolate) dianion O−C≡C−O are known. They are not however prepared from ethynediol, but by the reduction of carbon monoxide. Potassium acetylenediolate (K2C2O2) was first obtained by Liebig in 1834, from the reaction of carbon monoxide with metallic potassium; but for a long time the product was assumed to be "potassium carbonyl" (KCO). Over the next 130 years were described the "carbonyls" of sodium (Johannis, 1893), barium (Gunz and Mentrel, 1903), strontium (Roederer, 1906), and lithium, rubidium, and caesium (Pearson, 1933). The reaction was eventually shown to yield a mixture of the potassium acetylenediolate K
2C
2O
2 and potassium benzenehexolate K
6C
6O
6.

The structure of these salts was clarified only in 1963 by Büchner and Weiss.

Acetylenediolates can also be prepared by the rapid reaction of CO and a solution of the corresponding metal in liquid ammonia at low temperature. 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.

Coordination complexes

Acetylenediol can form coordination compounds, such as Cl where dmpe is bis(dimethylphosphino)ethane.

Acetylenediolate and related anions such as deltate C
3O
3 and squarate C
4O
4 have been obtained from carbon monoxide under mild conditions by reductive coupling of CO ligands in organouranium complexes.

See also

References

  1. Terlouw, Johan K.; Burgers, Peter C.; van Baar, Ben L. M.; Weiske, Thomas; Schwarz, Helmut (1986). "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". CHIMIA. 40: 357–359. Retrieved 1 August 2009.
  2. Maier, Günther; Rohr, Christine (1995). "Ethynediol: Photochemical generation and matrix-spectroscopic identification". Liebigs Annalen. 1996 (3): 307–309. doi:10.1002/jlac.199619960303.
  3. Wang, Jia; Turner, Andrew M.; Marks, Joshua H.; Zhang, Chaojiang; Kleimeier, N. Fabian; Bergantini, Alexandre; Singh, Santosh K.; Fortenberry, Ryan C.; Kaiser, Ralf I. (1 June 2024). "Preparation of Acetylenediol (HOCCOH) and Glyoxal (HCOCHO) in Interstellar Analog Ices of Carbon Monoxide and Water". The Astrophysical Journal. 967 (2): 79. doi:10.3847/1538-4357/ad3c3e.
  4. Justus Liebig (1834), Annalen der Chemie und Pharmacie, volume 11, p. 182. Cited by Raymond N. Vrtis et al. (1988), JACS p. 7564.
  5. ^ T. G. Pearson (1933), Carbonyls of Lithium, Rubidium and Caesium. Nature, volume 131, pp. 166–167 (4 February 1933). doi:10.1038/131166b0
  6. 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
  7. 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
  8. 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
  9. 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.
  10. 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
  11. 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 2(μ-η:η-C2O2) Journal of the American Chemical Society, volume 130, issue 42, pages 13816–13817. doi:10.1021/ja8059792
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