| Revision as of 16:03, 3 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit |
Latest revision as of 17:44, 19 December 2024 edit undoProject Osprey (talk | contribs)Extended confirmed users9,967 editsm →Synthesis and reactions |
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{{chembox |
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{{Chembox |
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| Name = Nitrosylsulfuric acid |
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|verifiedrevid = 434912557 |
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| ImageFile = Nitrosylsulfuric acid structure.svg |
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|Name = Nitrosylsulfuric acid |
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| ImageSize = 200px |
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|ImageFile = Nitrosylsulfuric acid structure.svg |
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| ImageName = Structural formula of nitrosylsulfuric acid |
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|ImageAlt = Structural formula of nitrosylsulfuric acid |
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| ImageFile1 = Nitrosylsulfuric-acid-3D-balls-B.png |
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|ImageFile1 = Nitrosylsulfuric acid molecule ball.png |
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| ImageSize1 = 180px |
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|ImageSize1 = 190px |
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| ImageName1 = Ball-and-stick model |
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|ImageAlt1 = Ball-and-stick model of the nitrosylsulfuric acid molecule |
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| IUPACName = Nitrosylsulfuric acid |
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|IUPACName = Nitrosylsulfuric acid |
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| OtherNames = nitrosonium bisulfate, chamber crystals |
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|OtherNames = nitrosonium bisulfate, chamber crystals |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| SMILES = O=NOS(=O)(=O)O |
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|SMILES = O=NOS(=O)(=O)O |
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| ChemSpiderID = 74147 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 82157 |
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|ChemSpiderID = 74147 |
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| InChI = 1/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5) |
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|PubChem = 82157 |
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| InChIKey = VQTGUFBGYOIUFS-UHFFFAOYAM |
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| StdInChI = 1S/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5) |
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|InChI = 1/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5) |
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| StdInChIKey = VQTGUFBGYOIUFS-UHFFFAOYSA-N |
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|InChIKey = VQTGUFBGYOIUFS-UHFFFAOYAM |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo = 7782-78-7 |
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|StdInChI = 1S/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5) |
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| RTECS = |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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|StdInChIKey = VQTGUFBGYOIUFS-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|CASNo_Ref = {{cascite|correct|??}} |
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| Formula = HNO<sub>5</sub>S |
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|CASNo = 7782-78-7 |
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| MolarMass = 127.08 g/mol |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| Appearance = pale yellow crystals |
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|UNII = 40K942UPM8 |
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| Density = 1.612 g/mL in<br /> 40% sulfuric acid soln |
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}} |
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| Solubility = decomposes |
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|Section2={{Chembox Properties |
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| SolubleOther = soluble in ] |
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|Formula = {{chem2|HSO4NO}} |
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| MeltingPt = 73.5 °C |
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|MolarMass = 127.08 g/mol |
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| BoilingPt = decomposes |
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|Appearance = Pale yellow crystals<ref name=EROS>{{cite book |chapter= Nitrosylsulfuric Acid |author= George A. Olah, G. K. Surya Prakash, Qi Wang, Xing-Ya Li |title= Encyclopedia of Reagents for Organic Synthesis |doi= 10.1002/047084289X.rn060 |journal= E-EROS Encyclopedia of Reagents for Organic Synthesis |year= 2001 |isbn= 978-0471936237}}</ref> |
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| pKb = |
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|Density = 1.865 g/mL in<br/> 40% sulfuric acid soln <ref>{{cite web |url=https://www.sigmaaldrich.com/AT/de/product/aldrich/517070 | title=Nitrosylsulfuric acid solution | publisher=Merck}}</ref> |
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}} |
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|Solubility = Decomposes |
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| Section3 = {{Chembox Structure |
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|SolubleOther = Soluble in ]<ref name=EROS/> |
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| CrystalStruct = |
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|MeltingPtC = 70 |
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|MeltingPt_ref = <ref name=EROS/> |
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| Section7 = {{Chembox Hazards |
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|BoilingPt = Decomposes |
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| ExternalMSDS = |
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| MainHazards = oxidizer |
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|Section7={{Chembox Hazards |
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| RPhrases = |
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|MainHazards = Oxidizer |
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| SPhrases = |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherAnions = ] |
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|OtherAnions = ] |
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| OtherCations = ] |
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|OtherCations = ] |
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| OtherCpds = ] |
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|OtherCompounds = ] |
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'''Nitrosylsulfuric acid''' is the ] with the formula {{chem2|HSO4NO}}. It is a colourless solid that is used industrially in the production of ],<ref name=Ullmann>{{cite encyclopedia |author1=Ritz, J. |author2=Fuchs, H. |author3=Kieczka, H. |author4=Moran, W. C. |encyclopedia= Ullmann's Encyclopedia of Industrial Chemistry |publisher= Wiley-VCH |location= Weinheim |year= 2002 |doi= 10.1002/14356007.a05_031 |chapter=Caprolactam |isbn=978-3527306732}}</ref> and was formerly part of the ] for producing ]. The compound is the mixed ] of sulfuric acid and ]. |
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'''Nitrosylsulfuric acid''' is the ] with the formula NOHSO<sub>4</sub>. |
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In organic chemistry, it is used as a reagent for ], as a ], and as an ].<ref name=EROS/> |
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This salt is a source of the NO<sup>+</sup> ion, It can also be viewed as the mixed ] of ] and ]: |
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: HNO<sub>2</sub> + H<sub>2</sub>SO<sub>4</sub> → NOHSO<sub>4</sub> +H<sub>2</sub>O |
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==Synthesis and reactions== |
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NOHSO<sub>4</sub> is useful in ] to prepare ]s from ]s. A typical procedure entails dissolving ] in concentrated sulfuric acid in an ice bath.<ref>{{OrgSynth | author = Hodgson, H, H.; Mahadevan, A. P. Ward, E. R. | title = 1,4-Dinitronaphthalene | collvol = 3 | collvolpages = 341 | prep = cv3p0341 | year = 1955}} (diazodization followed by treatment with nitrite)</ref><ref>{{OrgSynth | author = Sandin, R. B.; Cairns, T. L. | title = 1,2,3-Triiodo-5-nitrobenzene | collvol = 2 | collvolpages = 604 | year = 1943 | prep = cv2p0604}} (diazodization followed by treatment with iodide)</ref> |
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A typical procedure entails dissolving ] in cold sulfuric acid:<ref>{{OrgSynth |author1=Hodgson, H. H.|author2=Mahadevan, A. P.|author3=Ward, E. R. |title= 1,4-Dinitronaphthalene |collvol= 3 |collvolpages= 341 |prep= cv3p0341 |year= 1955}} (diazodization followed by treatment with nitrite)</ref><ref>{{OrgSynth |author1=Sandin, R. B.|author2=Cairns, T. L. |title= 1,2,3-Triiodo-5-nitrobenzene |collvol= 2 |collvolpages= 604 |year= 1943 |prep= cv2p0604}} (diazodization followed by treatment with iodide)</ref> |
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:{{chem2 | HNO2 + H2SO4 -> HSO4NO + H2O }} |
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Related NO-delivery reagents include ], BF<sub>4</sub>, and ]. |
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It can also be prepared by the reaction of ] and ].<ref>{{Cite book |author1=Coleman, G. H. |author2=Lillis, G. A. |author3=Goheen, G. E. |chapter=Nitrosyl Chloride |title= Inorganic Syntheses |year= 1939 |volume= 1 |pages= 55–59 |doi= 10.1002/9780470132326.ch20 |isbn=9780470132326}} This procedure generates the nitrosylsulfuric acid as an intermediate en route to NOCl.</ref> |
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{{chem2|HSO4NO}} is used in ] to prepare ]s from ]s, for example in the ]. Related NO-delivery reagents include ] {{chem2|+-}} and ]. |
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In industry, the nitrosodecarboxylation reaction between nitrosylsulfuric acid and ] is used to generate caprolactam:<ref name=Ullmann/> This is known as the ] process |
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:] |
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==Safety== |
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Nitrosylsulfuric acid is a hazardous material and precautions are indicated.<ref name=EROS/> |
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==References== |
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==References== |
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{{Hydrogen compounds}} |
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{{Hydrogen compounds}} |
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{{Inorganic-compound-stub}} |
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