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Revision as of 01:48, 13 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|error← Previous edit Latest revision as of 02:07, 25 December 2023 edit undo1234qwer1234qwer4 (talk | contribs)Extended confirmed users, Page movers197,945 edits added Category:Substances discovered in the 19th century using HotCat 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443368412
| Watchedfields = changed
⚫ | Reference = <ref name=Aldrich> at ]</ref>
⚫ | verifiedrevid = 477240442
⚫ | ImageFile = Acetylenedicarboxylic acid.svg
⚫ | Reference = <ref name=Aldrich>{{cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/a15207 | title = Acetylenedicarboxylic acid | publisher = ]}}</ref>
⚫ | ImageSize = 200px
⚫ | ImageFile = Acetylenedicarboxylic acid.svg
⚫ | ImageName = Structural formula of acetylenedicarboxylic acid
⚫ | ImageSize =
⚫ | ImageFile1 = Acetylenedicarboxylic-acid-3D-balls.png
⚫ | ImageName = Structural formula of acetylenedicarboxylic acid
⚫ | ImageSize1 = 220px
⚫ | ImageFile1 = Acetylenedicarboxylic-acid-3D-balls.png
⚫ | ImageName1 = Ball-and-stick model
⚫ | ImageSize1 = 220px
⚫ | IUPACName = But-2-ynedioic acid
⚫ | ImageName1 = Ball-and-stick model
⚫ | OtherNames = 2-Butynedioic acid
⚫ | PIN = But-2-ynedioic acid
⚫ |Section1 = {{Chembox Identifiers
⚫ | OtherNames = 2-Butynedioic acid
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 362 | ChemSpiderID = 362
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
Line 18: Line 20:
| InChIKey = YTIVTFGABIZHHX-UHFFFAOYAA | InChIKey = YTIVTFGABIZHHX-UHFFFAOYAA
| SMILES1 = O=C(O)C#CC(=O)O | SMILES1 = O=C(O)C#CC(=O)O
| CASNo_Ref = {{cascite|changed|??}}
⚫ | CASNo = 142-45-0
⚫ | PubChem = 371
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 30781
| EC_number = 205-536-0
| Gmelin = 26624
| Beilstein = 878357
| 3DMet = B00569
| UNII = 2D2OJ4KO44
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8) | StdInChI = 1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YTIVTFGABIZHHX-UHFFFAOYSA-N | StdInChIKey = YTIVTFGABIZHHX-UHFFFAOYSA-N
⚫ | CASNo = 142-45-0
⚫ | PubChem = 371
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 30781
| SMILES = C(#CC(=O)O)C(=O)O | SMILES = C(#CC(=O)O)C(=O)O
}} }}
|Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = {{chem2|H2C4O4}}
| C = 4 | H = 2 | O = 4
| H=2|C=4|O=4
| Appearance=Crystalline solid | Appearance =Crystalline solid
| Density = | Density =
⚫ | MeltingPt=175–176 °C (dec.)<ref name="abbott"/><br>180–187 °C (dec.)<ref name=Aldrich/>
| MeltingPtC = 175 to 176
⚫ | BoilingPt =
⚫ | MeltingPt_notes = (decomposes)<ref name="abbott"/><br>180–187 °C (decomposes)<ref name=Aldrich/>
⚫ | Solubility =
⚫ | BoilingPt =
⚫ | Solubility =
| ConjugateBase = Hydrogen acetylenedicarboxylate (chemical formula {{chem2|HC4O4−}})
}} }}
|Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| RPhrases = {{R25}} {{R36/37/38}} | GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}
| GHSSignalWord = Danger
| SPhrases = {{S26}} {{S45}}
| HPhrases = {{H-phrases|301|314|315|319|335}}
| PPhrases = {{P-phrases|260|261|264|270|271|280|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|330|332+313|337+313|362|363|403+233|405|501}}
}} }}
}} }}


'''Acetylenedicarboxylic acid''' or '''butynedioic acid''' is an ] (a ]) with the formula C<sub>4</sub>H<sub>2</sub>O<sub>4</sub> or HO<sub>2</sub>C-C&equiv;C-CO<sub>2</sub>H. It is a crystalline solid that is soluble in ]. '''Acetylenedicarboxylic acid''' or '''butynedioic acid''' is an ] (a ]) with the formula {{chem2|H2C4O4}} or {{chem2|HO\sC(\dO)\sC\tC\sC(\dO)\sOH}}. It is a crystalline solid that is soluble in ].


The removal of two ]s yields the ] dianion C<sub>4</sub>O<sub>4</sub><sup>2&minus;</sup>, which consists only of ] and ], making it an ]. Partial ionization yields the monovalent ] anion HC<sub>4</sub>O<sub>4</sub><sup>&minus;</sup>. The removal of two ]s yields the acetylenedicarboxylate dianion {{chem2|C4O4(2-)}}, which consists only of ] and ], making it an ]. Partial ionization yields the monovalent hydrogen acetylenedicarboxylate anion {{chem2|HC4O4-}}.


The acid was first described in 1877 by Polish chemist ].<ref name="abbott"/><ref name="bandro">{{cite journal | last1 = Bandrowski | first1 = E. | title = Ueber Acetylendicarbonsäure |trans-title= On acetylenedicarboxylic acid | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 10 | pages = 838–842 | year = 1877 | doi = 10.1002/cber.187701001231| url = https://zenodo.org/record/1425134}}</ref><ref name="bandro2">{{cite journal | author = E. Bandrowski | year = 1879 | title = Weitere Beiträge zur Kenntniss der Acetylendicarbonsäure |trans-title= Further comments on the description of acetylenedicarboxylic acid | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 12 | issue = 2 | pages = 2212–2216 | doi = 10.1002/cber.187901202261| url = https://zenodo.org/record/1425196}}
The acid was first described in 1877 by Polish chemist ].<ref name="abbott"/><ref name="bandro">
⚫ </ref> It can be obtained by treating α,β-dibromo] with ] KOH in ] or ]. The reaction yields ] and potassium acetylenedicarboxylate. The salts are separated and the latter is treated with ].<ref name="abbott">{{OrgSynth | author = Abbott, T. W. |author2=Arnold, R. T. |author3=Thompson, R. B. | title = Acetylenedicarboxylic acid | collvol = 2 | collvolpages = 10 | prep = cv2p0010}}</ref>
E. Bandrowski (1877) ''Ueber Acetylendicarbonsäure'' Chemische Berichte band 10, 838–842 (1877).
</ref><ref name="bandro2">
E. Bandrowski (1879) ''Weitere Beiträge zur Kenntniss der Acetylendicarbonsäure.'' Berichte der deutschen chemischen Gesellschaft, volume 12, issue 2, 2212–2216. {{doi|10.1002/cber.187901202261}}
⚫ </ref> It can be obtained by treating α,β-dibromo] with ] KOH in ] or ]. The reaction yields ] and ]. The salts are separated and the latter is treated with ].<ref name="abbott">
{{OrgSynth | author = Abbott, T. W.; Arnold, R. T.; Thompson, R. B. | title = Acetylenedicarboxylic acid | collvol = 2 | collvolpages = 10 | prep = cv2p0010}}
</ref>


Acetylenedicarboxylic acid is used in the synthesis of ], an important laboratory reagent. Both the acid and the monobasic salt ] KC<sub>4</sub>HO<sub>4</sub> are commonly traded as laboratory chemicals. Acetylenedicarboxylic acid is used in the synthesis of ], an important laboratory reagent. The acid is commonly traded as a laboratory chemical. It can also be reacted with ] to produce ], a powerful dienophile for use in ]s.

Fatty alcohol esters of acetylenedicarboxylic acid can be used for the preparation of ] (PCM).<ref>{{Cite journal|last1=Daglar|first1=Ozgun|last2=Çakmakçı|first2=Emrah|last3=Hizal|first3=Gurkan|last4=Tunca|first4=Umit|last5=Durmaz|first5=Hakan|date=2020-05-05|title=Extremely fast synthesis of polythioether based phase change materials (PCMs) for thermal energy storage|url=http://www.sciencedirect.com/science/article/pii/S0014305720307163|journal=European Polymer Journal|language=en|volume=130|pages=109681|doi=10.1016/j.eurpolymj.2020.109681|s2cid=216326248 |issn=0014-3057}}</ref>

==Anions and salts==
'''Hydrogen acetylenedicarboxylate''' (often abbreviated as Hadc or HADC) is a ] ] of acetylenedicarboxylic acid with the formula {{chem2|HC4O4-}} or {{chem2|HO\sC(\dO)\sC\tC\sCO2(-)}}. The anion can be derived from acetylenedicarboxylic acid by removal of a single ] or from the ] dianion by addition of a proton. The name is also used for any ] of this anion. Salts of this anion are of interest in ] because they contain unusually short and strong ]s. In many crystalline salts (with the exception of the ] one), the HADC units form linear chains connected by strong hydrogen bonds. Each carboxylate group is usually planar; but the two groups may lie in different planes due to rotation about the carbon–carbon bonds. They are coplanar in the ] salts {{chem2|NaHC4O4*2H2O}} and {{chem2|CsHC4O4*2H2O}}, nearly coplanar in the ] salt {{chem2|+−}}, but off by 60° or more in other salts such as anhydrous {{chem2|KHC4O4}}.<ref name="leban">{{cite journal | doi = 10.1107/S010827019101154X| title = Structure of guanidinium hydrogen acetylenedicarboxylate, {{chem|CH|6|N|3|+}}·{{chem|C|4|HO|4−}}| journal = Acta Crystallographica Section C| volume = 48| issue = 5| pages = 821| year = 1992| last1 = Leban| first1 = I| last2 = Rupnik| first2 = A| doi-access =}}</ref>
<!--The crystal structures of all alkali-metal (including ammonium) acid salts have been reported: LiHadc.H20 (Mattes & Plescher, 1981), NaHadc.2H2O (Leban, 1974a), KHadc (Leban, Goli6 & Speakman, 1973), two forms of RbHadc (Blain, Speakman, Stamp, Goli6 & Leban, 1973), CsHadc.H2O (Gupta & Mahata, 1976), NH4Hadc (Leban, 1974b), as well as those of free acid: H2adc.2H2O (Dunitz & Robertson, 1947).-->

'''Potassium hydrogen acetylenedicarboxylate''' is a ] ] of HADC with chemical formula {{chem2|KHC4O4}} or {{chem2|K+HC4O4-}}, often abbreviated as KHadc. It is often called potassium hydrogen acetylenedicarboxylate or monopotassium acetylenedicarboxylate. The salt can be obtained from acetylenedicarboxylic acid and is a common laboratory starting material for the synthesis of other derivatives of that acid. In the crystalline form, the hydrogen acetylenedicarboxylate anions are joined into linear chains by uncommonly short hydrogen bonds.<ref name="leban2">{{Cite journal | doi = 10.1039/P29730000703| title = Crystal structures of the acid salts of some dibasic acids. Part VII. An X-ray study of potassium hydrogen acetylenedicarboxylate: The α-form| journal = J. Chem. Soc., Perkin Trans. 2| issue = 6| pages = 703–705| year = 1973| last1 = Leban| first1 = Ivan| last2 = Golič| first2 = Ljubo| last3 = Speakman| first3 = J. Clare}}</ref><ref name="miyakubo">{{cite thesis|first=Keisuke |last=Miyakubo |date=1994 |url=http://ir.library.osaka-u.ac.jp/metadb/up/LIBCLK003/f_1993-11213h.pdf |title=Nuclear magnetic resonance studies of dynamical structure of one-dimensional hydrogen-bonded system in the acid salts of some dicarboxylic acids |type=Ph.D. |publisher=Osaka University}}</ref>
]
'''Acetylenedicarboxylate''' (often abbreviated as ADC or adc) is a divalent anion with formula {{chem2|C4O4(2-)}} or {{chem2|(2−)}}; or any ] or ] thereof. The anion can be derived from acetylenedicarboxylic acid by the loss of two ]s. It is one of several ] which, like ] {{chem2|CO3(2-)}} and ] {{chem2|C2O4(2-)}}, consist solely of ] and ]. The ADC anion can aсt as a ] in ]es, such as the blue polymeric complex with ](]) and 2,2′-], {{chem2|(2-)*(C5H4N)2]_{''n''}|}}.<ref name="ming">{{cite journal|first1=Ming-xing |last1=Li |first2=Min |last2=Shao |first3=Hui |last3=Dai |first4=Bao-li |last4=An |first5=Wen-cong |last5=Lu |first6=Yu |last6=Zhu |first7=Chen-xia |last7=Du |date=2005 |title=Synthesis and Crystal Structure of a Novel Copper(II) Complex with Acetylenedicarboxylate and 2,2′-Bipyridine |journal=Chinese Chemical Letters |volume=16 |issue=10 |pages=1405–1408}}</ref><ref name="shao">{{cite journal|first1=Min |last1=Shao |first2=Ming-xing |last2=Li |first3=Hui |last3=Dai |first4=Wen-cong |last4=Lu |first5=Bao-li |last5=An |date=2007 |title=Polynuclear complexes incorporating Cu(II) and Mn(II) centers bridged by acetylenedicarboxylate: Structure, thermal stability and magnetism |journal=Journal of Molecular Structure |volume=829 |issue =1–3 |pages=155–160|doi=10.1016/j.molstruc.2006.06.021}}</ref> ](I) acetylenedicarboxylate ({{chem2|Tl2C4O4}}) decomposes at 195&nbsp;°C, leaving a residue of ] thallium powder.<ref>{{cite journal|first1=Ruth |last1=Ahlers |first2=Uwe |last2=Ruschewitz |date=2009 |title=Non-centrosymmetric coordination polymers based on thallium and acetylenedicarboxylate |journal=Solid State Sciences |volume=11 |issue=6 |pages=1058–1064|doi=10.1016/j.solidstatesciences.2009.03.008 |s2cid=95955193 |url=http://bib-pubdb1.desy.de/record/91913}}</ref>


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


==References== ==References==
{{Reflist}} {{Reflist}}


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