Acetylenedicarboxylic acid or butynedioic acid is an organic compound (a dicarboxylic acid) with the formula H2C4O4 or HO−C(=O)−C≡C−C(=O)−OH. It is a crystalline solid that is soluble in diethyl ether.
The removal of two protons yields the acetylenedicarboxylate dianion C4O2−4, which consists only of carbon and oxygen, making it an oxocarbon anion. Partial ionization yields the monovalent hydrogen acetylenedicarboxylate anion HC4O−4.
Fatty alcohol esters of acetylenedicarboxylic acid can be used for the preparation of phase change materials (PCM).[5]
Anions and saltsedit
Hydrogen acetylenedicarboxylate (often abbreviated as Hadc or HADC) is a monovalentanion of acetylenedicarboxylic acid with the formula HC4O−4 or HO−C(=O)−C≡C−CO−2. The anion can be derived from acetylenedicarboxylic acid by removal of a single proton or from the acetylenedicarboxylate dianion by addition of a proton. The name is also used for any salt of this anion. Salts of this anion are of interest in crystallography because they contain unusually short and strong hydrogen bonds. In many crystalline salts (with the exception of the lithium 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 hydrated salts NaHC4O4·2H2O and CsHC4O4·2H2O, nearly coplanar in the guanidinium salt [C(NH2)3]+[HC4O4]−, but off by 60° or more in other salts such as anhydrous KHC4O4.[6]
Potassium hydrogen acetylenedicarboxylate is a potassiumsalt of HADC with chemical formula KHC4O4 or K+HC4O−4, 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.[7][8]
Chemical structure of acetylenedicarboxylate
Acetylenedicarboxylate (often abbreviated as ADC or adc) is a divalent anion with formula C4O2−4 or [O2C−C≡C−CO2]2−; or any salt or ester thereof. The anion can be derived from acetylenedicarboxylic acid by the loss of two protons. It is one of several oxocarbon anions which, like carbonateCO2−3 and oxalateC2O2−4, consist solely of carbon and oxygen. The ADC anion can aсt as a ligand in organometallic complexes, such as the blue polymeric complex with copper(II) and 2,2′-bipyridine, [Cu2+[C4O4]2−·(C5H4N)2]n.[9][10]Thallium(I) acetylenedicarboxylate (Tl2C4O4) decomposes at 195 °C, leaving a residue of pyrophoric thallium powder.[11]
^ abcAbbott, T. W.; Arnold, R. T.; Thompson, R. B. "Acetylenedicarboxylic acid". Organic Syntheses.; Collective Volume, vol. 2, p. 10
^Bandrowski, E. (1877). "Ueber Acetylendicarbonsäure" [On acetylenedicarboxylic acid]. Berichte der Deutschen Chemischen Gesellschaft. 10: 838–842. doi:10.1002/cber.187701001231.
^E. Bandrowski (1879). "Weitere Beiträge zur Kenntniss der Acetylendicarbonsäure" [Further comments on the description of acetylenedicarboxylic acid]. Berichte der Deutschen Chemischen Gesellschaft. 12 (2): 2212–2216. doi:10.1002/cber.187901202261.
^Daglar, Ozgun; Çakmakçı, Emrah; Hizal, Gurkan; Tunca, Umit; Durmaz, Hakan (2020-05-05). "Extremely fast synthesis of polythioether based phase change materials (PCMs) for thermal energy storage". European Polymer Journal. 130: 109681. doi:10.1016/j.eurpolymj.2020.109681. ISSN 0014-3057. S2CID 216326248.
^Leban, I; Rupnik, A (1992). "Structure of guanidinium hydrogen acetylenedicarboxylate, CH 6N+ 3·C 4HO4− ". Acta Crystallographica Section C. 48 (5): 821. doi:10.1107/S010827019101154X.
^Leban, Ivan; Golič, Ljubo; Speakman, J. Clare (1973). "Crystal structures of the acid salts of some dibasic acids. Part VII. An X-ray study of potassium hydrogen acetylenedicarboxylate: The α-form". J. Chem. Soc., Perkin Trans. 2 (6): 703–705. doi:10.1039/P29730000703.
^Miyakubo, Keisuke (1994). Nuclear magnetic resonance studies of dynamical structure of one-dimensional hydrogen-bonded system in the acid salts of some dicarboxylic acids(PDF) (Ph.D.). Osaka University.
^Li, Ming-xing; Shao, Min; Dai, Hui; An, Bao-li; Lu, Wen-cong; Zhu, Yu; Du, Chen-xia (2005). "Synthesis and Crystal Structure of a Novel Copper(II) Complex with Acetylenedicarboxylate and 2,2′-Bipyridine". Chinese Chemical Letters. 16 (10): 1405–1408.
^Shao, Min; Li, Ming-xing; Dai, Hui; Lu, Wen-cong; An, Bao-li (2007). "Polynuclear complexes incorporating Cu(II) and Mn(II) centers bridged by acetylenedicarboxylate: Structure, thermal stability and magnetism". Journal of Molecular Structure. 829 (1–3): 155–160. doi:10.1016/j.molstruc.2006.06.021.
^Ahlers, Ruth; Ruschewitz, Uwe (2009). "Non-centrosymmetric coordination polymers based on thallium and acetylenedicarboxylate". Solid State Sciences. 11 (6): 1058–1064. doi:10.1016/j.solidstatesciences.2009.03.008. S2CID 95955193.
December 15, 2023
acetylenedicarboxylic, acid, butynedioic, acid, organic, compound, dicarboxylic, acid, with, formula, h2c4o4, crystalline, solid, that, soluble, diethyl, ether, namespreferred, iupac, name, ynedioic, acidother, names, butynedioic, acididentifierscas, number, m. Acetylenedicarboxylic acid or butynedioic acid is an organic compound a dicarboxylic acid with the formula H2C4O4 or HO C O C C C O OH It is a crystalline solid that is soluble in diethyl ether Acetylenedicarboxylic acid 1 NamesPreferred IUPAC name But 2 ynedioic acidOther names 2 Butynedioic acidIdentifiersCAS Number 142 45 0 N3D model JSmol Interactive imageInteractive image3DMet B00569Beilstein Reference 878357ChEBI CHEBI 30781 YChemSpider 362 YECHA InfoCard 100 005 033EC Number 205 536 0Gmelin Reference 26624KEGG C03248 YPubChem CID 371UNII 2D2OJ4KO44CompTox Dashboard EPA DTXSID3059715InChI InChI 1S C4H2O4 c5 3 6 1 2 4 7 8 h H 5 6 H 7 8 YKey YTIVTFGABIZHHX UHFFFAOYSA N YInChI 1 C4H2O4 c5 3 6 1 2 4 7 8 h H 5 6 H 7 8 Key YTIVTFGABIZHHX UHFFFAOYAASMILES C CC O O C O OO C O C CC O OPropertiesChemical formula H2C4O4Molar mass 114 056 g mol 1Appearance Crystalline solidMelting point 175 to 176 C 347 to 349 F 448 to 449 K decomposes 2 180 187 C decomposes 1 Conjugate base Hydrogen acetylenedicarboxylate chemical formula HC4O 4 HazardsGHS labelling PictogramsSignal word DangerHazard statements H301 H314 H315 H319 H335Precautionary statements P260 P261 P264 P270 P271 P280 P301 P310 P301 P330 P331 P302 P352 P303 P361 P353 P304 P340 P305 P351 P338 P310 P312 P321 P330 P332 P313 P337 P313 P362 P363 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references The removal of two protons yields the acetylenedicarboxylate dianion C4O2 4 which consists only of carbon and oxygen making it an oxocarbon anion Partial ionization yields the monovalent hydrogen acetylenedicarboxylate anion HC4O 4 The acid was first described in 1877 by Polish chemist Ernest Bandrowski 2 3 4 It can be obtained by treating a b 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 2 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 Fatty alcohol esters of acetylenedicarboxylic acid can be used for the preparation of phase change materials PCM 5 Anions and salts editHydrogen acetylenedicarboxylate often abbreviated as Hadc or HADC is a monovalent anion of acetylenedicarboxylic acid with the formula HC4O 4 or HO C O C C CO 2 The anion can be derived from acetylenedicarboxylic acid by removal of a single proton or from the acetylenedicarboxylate dianion by addition of a proton The name is also used for any salt of this anion Salts of this anion are of interest in crystallography because they contain unusually short and strong hydrogen bonds In many crystalline salts with the exception of the lithium 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 hydrated salts NaHC4O4 2H2O and CsHC4O4 2H2O nearly coplanar in the guanidinium salt C NH2 3 HC4O4 but off by 60 or more in other salts such as anhydrous KHC4O4 6 Potassium hydrogen acetylenedicarboxylate is a potassium salt of HADC with chemical formula KHC4O4 or K HC4O 4 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 7 8 nbsp Chemical structure of acetylenedicarboxylateAcetylenedicarboxylate often abbreviated as ADC or adc is a divalent anion with formula C4O2 4 or O2C C C CO2 2 or any salt or ester thereof The anion can be derived from acetylenedicarboxylic acid by the loss of two protons It is one of several oxocarbon anions which like carbonate CO2 3 and oxalate C2O2 4 consist solely of carbon and oxygen The ADC anion can ast as a ligand in organometallic complexes such as the blue polymeric complex with copper II and 2 2 bipyridine Cu2 C4O4 2 C5H4N 2 n 9 10 Thallium I acetylenedicarboxylate Tl2C4O4 decomposes at 195 C leaving a residue of pyrophoric thallium powder 11 See also editAcetylenedicarboxylate decarboxylase Oxalic acid AcetylenediolReferences edit a b Acetylenedicarboxylic acid Sigma Aldrich a b c Abbott T W Arnold R T Thompson R B Acetylenedicarboxylic acid Organic Syntheses Collective Volume vol 2 p 10 Bandrowski E 1877 Ueber Acetylendicarbonsaure On acetylenedicarboxylic acid Berichte der Deutschen Chemischen Gesellschaft 10 838 842 doi 10 1002 cber 187701001231 E Bandrowski 1879 Weitere Beitrage zur Kenntniss der Acetylendicarbonsaure Further comments on the description of acetylenedicarboxylic acid Berichte der Deutschen Chemischen Gesellschaft 12 2 2212 2216 doi 10 1002 cber 187901202261 Daglar Ozgun Cakmakci Emrah Hizal Gurkan Tunca Umit Durmaz Hakan 2020 05 05 Extremely fast synthesis of polythioether based phase change materials PCMs for thermal energy storage European Polymer Journal 130 109681 doi 10 1016 j eurpolymj 2020 109681 ISSN 0014 3057 S2CID 216326248 Leban I Rupnik A 1992 Structure of guanidinium hydrogen acetylenedicarboxylate CH6 N 3 C4 HO4 Acta Crystallographica Section C 48 5 821 doi 10 1107 S010827019101154X Leban Ivan Golic Ljubo Speakman J Clare 1973 Crystal structures of the acid salts of some dibasic acids Part VII An X ray study of potassium hydrogen acetylenedicarboxylate The a form J Chem Soc Perkin Trans 2 6 703 705 doi 10 1039 P29730000703 Miyakubo Keisuke 1994 Nuclear magnetic resonance studies of dynamical structure of one dimensional hydrogen bonded system in the acid salts of some dicarboxylic acids PDF Ph D Osaka University Li Ming xing Shao Min Dai Hui An Bao li Lu Wen cong Zhu Yu Du Chen xia 2005 Synthesis and Crystal Structure of a Novel Copper II Complex with Acetylenedicarboxylate and 2 2 Bipyridine Chinese Chemical Letters 16 10 1405 1408 Shao Min Li Ming xing Dai Hui Lu Wen cong An Bao li 2007 Polynuclear complexes incorporating Cu II and Mn II centers bridged by acetylenedicarboxylate Structure thermal stability and magnetism Journal of Molecular Structure 829 1 3 155 160 doi 10 1016 j molstruc 2006 06 021 Ahlers Ruth Ruschewitz Uwe 2009 Non centrosymmetric coordination polymers based on thallium and acetylenedicarboxylate Solid State Sciences 11 6 1058 1064 doi 10 1016 j solidstatesciences 2009 03 008 S2CID 95955193 Retrieved from https en wikipedia org w index php title Acetylenedicarboxylic acid amp oldid 1173469057, 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