Carborane acid (original) (raw)
حمض الكربوران هو حمض فائق له الصيغة (H(CHB11Cl11 وهو من مركبات الكربورانات، والتي هي مركبات تجميعية عنقودية من الكربون والبورون والهيدروجين، بالإضافة إلى الكلور كما في حالة مركب حمض الكربوران.
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| dbo:abstract | حمض الكربوران هو حمض فائق له الصيغة (H(CHB11Cl11 وهو من مركبات الكربورانات، والتي هي مركبات تجميعية عنقودية من الكربون والبورون والهيدروجين، بالإضافة إلى الكلور كما في حالة مركب حمض الكربوران. (ar) Carborane acids H(CXB11Y5Z6) (X, Y, Z = H, Alk, F, Cl, Br, CF3) are a class of superacids, some of which are estimated to be at least one million times stronger than 100% pure sulfuric acid in terms of their Hammett acidity function values (H0 ≤ –18) and possess computed pKa values well below –20, establishing them as some of the strongest known Brønsted acids. The best-studied example is the highly chlorinated derivative H(CHB11Cl11). The acidity of H(CHB11Cl11) was found to vastly exceed that of triflic acid, CF3SO3H, and bistriflimide, (CF3SO2)2NH, compounds previously regarded as the strongest isolable acids. Their high acidities stem from the extensive delocalization of their conjugate bases, carboranate anions (CXB11Y5Z6−), which are usually further stabilized by electronegative groups like Cl, F, and CF3. Due to the lack of oxidizing properties and the exceptionally low nucleophilicity and high stability of their conjugate bases, they are the only superacids known to protonate C60 fullerene without decomposing it. Additionally, they form stable, isolable salts with protonated benzene, C6H7+, the parent compound of the Wheland intermediates encountered in electrophilic aromatic substitution reactions. The fluorinated carborane acid, H(CHB11F11), is even stronger than chlorinated carborane acid. It is able to protonate butane to form tert-butyl cation at room temperature and is the only known acid to protonate carbon dioxide to give the bridged cation, [H(CO2)2]+, making it possibly the strongest known acid. In particular, CO2 does not undergo observable protonation when treated with the mixed superacids HF-SbF5 or HSO3F-SbF5. As a class, the carborane acids form the most acidic group of well-defined, isolable substances known, far more acidic than previously known single-component strong acids like triflic acid or perchloric acid. In certain cases, like the nearly perhalogenated derivatives mentioned above, their acidities rival (and possibly exceed) those of the traditional mixed Lewis-Brønsted superacids like magic acid and fluoroantimonic acid. (However, a head-to-head comparison has not been possible thus far, due to the lack of a measure of acidity that is suitable for both classes of acids: pKa values are ill-defined for the chemically complex mixed acids while H0 values cannot be measured for the very high melting carborane acids). (en) 카보레인산(Carborane acid)은 화학식 H(CXB11Y5Z6)를 가지는 화합물들의 총칭으로, 대부분 초강산에 속한다. 2004년 캘리포니아 대학의 와 그의 동료에 의해 발견되었다. (ko) カルボラン酸 (カルボランさん、英: carborane acid) はホウ素原子11個と炭素原子1個からなる二十面体型の分子であり、分子式はH(CHB11Cl11)である。カルボランの塩素置換体であり超酸である。2004年、カリフォルニア大学リバーサイド校のクリストファー・リードが発見した。 (ja) Kwas karboranowy H(CHB11Cl11) to związek chemiczny, superkwas, w którym rolę reszty kwasowej spełnia klasterowy karboran. Jest to aktualnie kwas o największej mocy, który można wyodrębnić z roztworu w stanie wolnym. Mimo swojej dużej mocy, nie ma on własności żrących i w odróżnieniu od innych superkwasów można go przechowywać w zwykłych naczyniach szklanych, a nawet w naczyniach ze stali kwasoodpornej. Własności tego kwasu wynikają z faktu, że jego reszta jest zbudowana z jednego z najbardziej trwałych ze wszystkich znanych anionów klasterowych, który składa się z sieci 11 atomów boru i jednego atomu węgla do którego przyczepiony jest „kwaśny” atom wodoru. Kwas ten jest ok. milion razy mocniejszy od 100% kwasu siarkowego i kilkaset razy mocniejszy od najsilniejszego wcześniej znanego superkwasu, który udało się wyodrębnić w stanie wolnym, kwasu triflowego. Kwas karboranowy jest jednak znacznie słabszy od mieszaniny fluorowodoru (HF) i pentafluorku antymonu (SbF5), nazywanej czasem kwasem fluoroantymonowym, którego jednak nie udało się jak dotąd wyodrębnić w stanie wolnym. Kwas karboranowy został otrzymany i zbadany przez zespół z Uniwersytetu Kalifornijskiego w Riverside w 2004 r. (pl) Ácidos carborano H(CXB11Y5Z6) (X, Y, Z = H, Alk, F, Cl, Br, CF3) são uma classe de superácidos. Estima-se que são um milhão de vezes mais fortes do que o ácido sulfúrico alguns 100% em termos das sua função de acidez de Hammet com valores (H 0 ≤ -18) e possuem os valores de pK a abaixo dos -20, estabelecendo-los como alguns dos mais fortes ácidos de Bronsted conhecidos. O exemplo mais bem estudado é o derivado altamente clorado H (CHB11Cl11 ). Verificou-se que a acidez do H(CHB11Cl11 ) excedia largamente a do ácido tríflico, CF3SO3H, e bistriflimide, (CF3SO2)2NH, compostos anteriormente considerados como os ácidos isolados mais fortes. Suas altas acidez derivam da extensa deslocalização de suas bases conjugadas, ânions carboranato (CXB11Y5Z6- ), que são geralmente mais estabilizados por grupos eletronegativos como Cl, F e CF 3 . Devido à falta de propriedades oxidantes e o excepcionalmente baixa nucleofilicidade e alta estabilidade das suas bases conjugadas, que são os únicos superácidos conhecidos para protonar C60 fulereno sem o decompor. Além disso, eles formam sais estáveis, isoláveis com benzeno protonado, C 6H7+, o composto parental dos intermediários Wheland encontradas em reações de substituição electrófila aromática. O ácido fluorado carborano, H(CHB 11F11), é ainda mais forte que o ácido carborano clorado. É capaz de protonar o butano para formar o cátion tert-butílico à temperatura ambiente e é o único ácido conhecido a protonar o dióxido de carbono para dar o cátion em ponte, [H(CO 2)2]+, tornando-o possivelmente o ácido mais forte conhecido. Em particular, o dióxido de carbono não sofre protonação observável quando tratado com os superácidos mistos HF-SBF5 ou HSO3 F-5 SBF. Como classe, os ácidos carborano formam o grupo mais ácido de substâncias conhecidas, bem definidas e isoláveis, muito mais ácidas do que os ácidos fortes de componente único conhecidos anteriormente, como o ácido triflico ou o ácido perclórico . Em certos casos, como os derivados quase peralogenados mencionados acima, suas aci- midades rivalizam (e possivelmente excedem) as dos superácidos mistos Lewis-Brønsted tradicionais, como o ácido mágico e o ácido fluoroantimônico . (No entanto, uma comparação direta não foi possível até agora, devido à falta de uma medida de acidez que é adequada para ambas as classes de ácidos: pKa valores são mal definidos para os ácidos mistos quimicamente complexos enquanto Os valores de H 0 não podem ser medidos para os ácidos carborano de fusão muito elevada). (pt) Karboransyra, summaformel H(CHB11Cl11), är en supersyra – betydelsefull inom den organiska kemin, bland annat vid utveckling av vitaminpreparat. Karboransyra fräter inte på glas och kan därför lagras i glaskärl, till skillnad från många andra supersyror. (sv) 碳硼烷酸（化學式：H(CHB11Cl11)，英語：Carborane acid） 為一種超強酸，是最強的單一分子酸，酸性為硫酸的一百萬倍、氟磺酸的數百倍。 (zh) 2,3,4,5,6,7,8,9,10,11,12-Ундекахлор-1-карба-клозо-додекаборан(12) (журналистское название Карборановая кислота) — одна из самых сильных кислот (суперкислота), полученных в начале XXI века. Химическая формула — H(CHB11Cl11). Карборановая часть молекулы имеет икосаэдрическую структуру. (ru) |
| dbo:thumbnail | wiki-commons:Special:FilePath/Carborane-acid-3D-balls.png?width=300 |
| dbo:wikiPageExternalLink | http://www.reedgrouplab.ucr.edu/projects/strong_gentle.html https://web.archive.org/web/20120313203844/http:/www.albochem.com/wps/wp-content/2008/12/o-carboranemsds.pdf |
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| dbo:wikiPageLength | 23715 (xsd:nonNegativeInteger) |
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| dbo:wikiPageWikiLink | dbr:Carbon dbr:Electrophilic_aromatic_substitution dbr:Bistriflimide dbr:Boron dbr:Decaborane dbc:Superacids dbr:Arenium_ion dbr:Hydrogen dbr:Perchloric_acid dbr:Electronegative dbr:Protonation dbc:Organoboron_compounds dbr:Magic_acid dbr:Fullerene dbr:Hammett_acidity_function dbr:Triflic_acid dbr:Acid_dissociation_constant dbr:Fluoroantimonic_acid dbc:Cluster_chemistry dbr:Chlorine dbr:Sulfuric_acid dbr:Superacid dbr:Gas-phase_acidity dbr:File:Boron-Based_Carborane_Acid_Figure_3..jpg dbr:File:Boron-Based_Carborane_Acid_Figure_4..jpg dbr:File:Carborane-acid.png dbr:File:Carborane_figure.png dbr:File:Generalcarboraneanion.png |
| dbp:imagecaption | Ball-and-stick model of [CHB11Cl11]−. . (en) Colour scheme: (en) boron − pink, (en) carbon − black. (en) chlorine − green, (en) hydrogen − white, (en) |
| dbp:imagefile | Carborane-acid-3D-balls.png (en) |
| dbp:name | Carborane acids H[CXB11Y5Z6] (en) |
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| dcterms:subject | dbc:Superacids dbc:Organoboron_compounds dbc:Cluster_chemistry |
| gold:hypernym | dbr:Times |
| rdf:type | owl:Thing dbo:Person dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 yago:WikicatBoronCompounds yago:WikicatCarbonCompounds yago:WikicatMineralAcids yago:WikicatOrganoboronCompounds yago:Abstraction100002137 yago:Acid114607521 yago:BinaryCompound114618834 yago:Chemical114806838 yago:Cognition100023271 yago:Compound105870180 yago:Compound114818238 yago:Concept105835747 yago:Content105809192 yago:Hydride114910748 yago:Idea105833840 yago:Material114580897 yago:Matter100020827 yago:Part113809207 yago:PhysicalEntity100001930 yago:PsychologicalFeature100023100 yago:Relation100031921 yago:WikicatHydrides yago:WikicatHydrogenCompounds yago:WikicatInorganicCarbonCompounds dbo:ChemicalCompound yago:Substance100019613 yago:Whole105869584 |
| rdfs:comment | حمض الكربوران هو حمض فائق له الصيغة (H(CHB11Cl11 وهو من مركبات الكربورانات، والتي هي مركبات تجميعية عنقودية من الكربون والبورون والهيدروجين، بالإضافة إلى الكلور كما في حالة مركب حمض الكربوران. (ar) 카보레인산(Carborane acid)은 화학식 H(CXB11Y5Z6)를 가지는 화합물들의 총칭으로, 대부분 초강산에 속한다. 2004년 캘리포니아 대학의 와 그의 동료에 의해 발견되었다. (ko) カルボラン酸 (カルボランさん、英: carborane acid) はホウ素原子11個と炭素原子1個からなる二十面体型の分子であり、分子式はH(CHB11Cl11)である。カルボランの塩素置換体であり超酸である。2004年、カリフォルニア大学リバーサイド校のクリストファー・リードが発見した。 (ja) Karboransyra, summaformel H(CHB11Cl11), är en supersyra – betydelsefull inom den organiska kemin, bland annat vid utveckling av vitaminpreparat. Karboransyra fräter inte på glas och kan därför lagras i glaskärl, till skillnad från många andra supersyror. (sv) 碳硼烷酸（化學式：H(CHB11Cl11)，英語：Carborane acid） 為一種超強酸，是最強的單一分子酸，酸性為硫酸的一百萬倍、氟磺酸的數百倍。 (zh) 2,3,4,5,6,7,8,9,10,11,12-Ундекахлор-1-карба-клозо-додекаборан(12) (журналистское название Карборановая кислота) — одна из самых сильных кислот (суперкислота), полученных в начале XXI века. Химическая формула — H(CHB11Cl11). Карборановая часть молекулы имеет икосаэдрическую структуру. (ru) Carborane acids H(CXB11Y5Z6) (X, Y, Z = H, Alk, F, Cl, Br, CF3) are a class of superacids, some of which are estimated to be at least one million times stronger than 100% pure sulfuric acid in terms of their Hammett acidity function values (H0 ≤ –18) and possess computed pKa values well below –20, establishing them as some of the strongest known Brønsted acids. The best-studied example is the highly chlorinated derivative H(CHB11Cl11). The acidity of H(CHB11Cl11) was found to vastly exceed that of triflic acid, CF3SO3H, and bistriflimide, (CF3SO2)2NH, compounds previously regarded as the strongest isolable acids. (en) Kwas karboranowy H(CHB11Cl11) to związek chemiczny, superkwas, w którym rolę reszty kwasowej spełnia klasterowy karboran. Jest to aktualnie kwas o największej mocy, który można wyodrębnić z roztworu w stanie wolnym. Kwas karboranowy został otrzymany i zbadany przez zespół z Uniwersytetu Kalifornijskiego w Riverside w 2004 r. (pl) Ácidos carborano H(CXB11Y5Z6) (X, Y, Z = H, Alk, F, Cl, Br, CF3) são uma classe de superácidos. Estima-se que são um milhão de vezes mais fortes do que o ácido sulfúrico alguns 100% em termos das sua função de acidez de Hammet com valores (H 0 ≤ -18) e possuem os valores de pK a abaixo dos -20, estabelecendo-los como alguns dos mais fortes ácidos de Bronsted conhecidos. O exemplo mais bem estudado é o derivado altamente clorado H (CHB11Cl11 ). Verificou-se que a acidez do H(CHB11Cl11 ) excedia largamente a do ácido tríflico, CF3SO3H, e bistriflimide, (CF3SO2)2NH, compostos anteriormente considerados como os ácidos isolados mais fortes. (pt) |
| rdfs:label | حمض الكربوران (ar) Carborane acid (en) カルボラン酸 (ja) 카보레인산 (ko) Kwas karboranowy (pl) Ácido carborano (pt) Карборановая кислота (ru) Karboransyra (sv) 碳硼烷酸 (zh) |
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| prov:wasDerivedFrom | wikipedia-en:Carborane_acid?oldid=1124356017&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/Boron-Based_Carborane_Acid_Figure_3..jpg wiki-commons:Special:FilePath/Boron-Based_Carborane_Acid_Figure_4..jpg wiki-commons:Special:FilePath/Carborane-acid-3D-balls.png wiki-commons:Special:FilePath/Carborane-acid.png wiki-commons:Special:FilePath/Carborane_figure.png wiki-commons:Special:FilePath/Generalcarboraneanion.png |
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| foaf:name | Carborane acids H[CXB11Y5Z6] (en) |
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