词条 | Acetylenedicarboxylic acid |
释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477240442 | Reference = [1] | ImageFile = Acetylenedicarboxylic acid.svg | ImageSize = | ImageName = Structural formula of acetylenedicarboxylic acid | ImageFile1 = Acetylenedicarboxylic-acid-3D-balls.png | ImageSize1 = 220px | ImageName1 = Ball-and-stick model | PIN = But-2-ynedioic acid | OtherNames = 2-Butynedioic acid |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 362 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C03248 | InChI = 1/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8) | InChIKey = YTIVTFGABIZHHX-UHFFFAOYAA | SMILES1 = O=C(O)C#CC(=O)O | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YTIVTFGABIZHHX-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 142-45-0 | PubChem = 371 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 30781 | SMILES = C(#CC(=O)O)C(=O)O |Section2={{Chembox Properties | C=4 | H=2 | O=4 | Appearance =Crystalline solid | Density = | MeltingPtC = 175 to 176 | MeltingPt_notes = (decomposes)[2] 180–187 °C (decomposes)[1] | BoilingPt = | Solubility = | ConjugateBase = Hydrogenacetylenedicarboxylate (chemical formula HC4O4−) |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | RPhrases = {{R25}} {{R36/37/38}} | SPhrases = {{S26}} {{S45}} }} Acetylenedicarboxylic acid or butynedioic acid is an organic compound (a dicarboxylic acid) with the formula C4H2O4 or The removal of two protons yields the acetylenedicarboxylate dianion C4O42−, which consists only of carbon and oxygen, making it an oxocarbon anion. Partial ionization yields the monovalent hydrogenacetylenedicarboxylate anion HC4O4−. The acid was first described in 1877 by Polish chemist Ernest Bandrowski.[2][2][3] It can be obtained by treating α,β-dibromosuccinic acid with potassium hydroxide KOH in methanol or ethanol. The reaction yields potassium bromide and potassium acetylenedicarboxylate. The salts are separated and the latter is treated with sulfuric acid.[4] Acetylenedicarboxylic acid is used in the synthesis of dimethyl acetylenedicarboxylate, an important laboratory reagent. The acid is commonly traded as a laboratory chemical. It can also be reacted with sulfur tetrafluoride to produce hexafluoro-2-butyne, a powerful dienophile for use in Diels-Alder reactions. Anions and saltsHydrogenacetylenedicarboxylate (often abbreviated as Hadc or HADC) is a monovalent anion of acetylenedicarboxylic acid with the formula C4HO4− orSee also
References1. ^1 {{cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/a15207 | title = Acetylenedicarboxylic acid | publisher = Sigma-Aldrich}} 2. ^{{cite journal | last1 = Bandrowski | first1 = E. | title = Ueber Acetylendicarbonsäure | journal = Berichte der deutschen chemischen Gesellschaft | volume = 10 | pages = 838 | year = 1877 | doi = 10.1002/cber.187701001231}} 3. ^{{cite journal | author = E. Bandrowski | year = 1879 | title = Weitere Beiträge zur Kenntniss der Acetylendicarbonsäure | journal = Berichte der deutschen chemischen Gesellschaft | volume = 12 | issue = 2 | pages = 2212–2216 | doi = 10.1002/cber.187901202261}} 4. ^1 2 {{OrgSynth | author = Abbott, T. W. |author2=Arnold, R. T. |author3=Thompson, R. B. | title = Acetylenedicarboxylic acid | collvol = 2 | collvolpages = 10 | prep = cv2p0010}} 5. ^{{cite journal | doi = 10.1107/S010827019101154X| title = Structure of guanidinium hydrogen acetylenedicarboxylate, CH6N3+.C4HO4−| journal = Acta Crystallographica Section C| volume = 48| issue = 5| pages = 821| year = 1992| last1 = Leban| first1 = I| last2 = Rupnik| first2 = A}} 6. ^{{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| year = 1973| last1 = Leban| first1 = Ivan| last2 = Golič| first2 = Ljubo| last3 = Speakman| first3 = J. Clare}} 7. ^Keisuke Miyakubo (1994). Nuclear magnetic resonance studies of dynamicals structure of one-dimensional hyrogen-bonded system in the acid salts of some dicarboxylic acids. Ph.D. Thesis, Osaka University. 8. ^Ming Xing LI, Min SHAO, Hui DAI, Bao Li AN, Wen Cong LU, Yu ZHU, Chen Xia DU (2005), "Synthesis and Crystal Structure of a Novel Copper (II) Complex with Acetylenedicarboxylate and 2,2'-Bipyridine". Chinese Chemical Letters, volume 16, issue 10, pp. 1405–1408. 9. ^Min Shao, Ming-Xing Li, Hui Dai, Wen-Cong Lu and Bao-Li An (2007), "Polynuclear complexes incorporating Cu(II) and Mn(II) centers bridged by acetylenedicarboxylate: Structure, thermal stability and magnetism". Journal of Molecular Structure, volume 829, issues 1–3, pp. 155–160. 10. ^Ruth Ahlers and Uwe Ruschewitz (2009), "Non-centrosymmetric coordination polymers based on thallium and acetylenedicarboxylate". Solid State Sciences, volume 11, issue 6, pp. 1058–1064. 2 : Alkynes|Dicarboxylic acids |
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