| Revision as of 12:46, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477123424 of page Trioxidane for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 13:28, 13 December 2024 edit DMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,457 edits Moving from Category:Hydrogen compounds to Category:Oxoacids using Cat-a-lot |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Redirect|Hydrogen trioxide|HO<sub>3</sub>|hydrogen ozonide}} |
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{{Distinguish|Trioxane}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 470616332 |
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| verifiedrevid = 477175194 |
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| ImageFile = Trioxidan.svg |
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| ImageFile = Trioxidan.svg |
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⚫ |
| ImageName = Structural formula of trioxidane |
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| ImageSize = 121 |
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| ImageFile2 = Trioxidane structure.png |
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| ImageName = Structural formula of trioxidane with explicit hydrogens |
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| PIN = Trioxidane (only preselected name)<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 1024 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| IUPACName = Trioxidane |
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| OtherNames = Dihydrogen trioxide<br>Hydrogen trioxide<br>Water-Air |
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| SystematicName = Dihydrogen trioxide |
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| OtherNames = Hydrogen trioxide<br>Dihydroxy ether |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = <!-- blanked - oldvalue: 14699-99-1 --> |
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| CASNo = 14699-99-1 |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|correct}} |
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| PubChem = 166717 |
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| PubChem = 166717 |
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| PubChem_Ref = {{Pubchemcite|correct|PubChem}} |
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| ChemSpiderID = 145859 |
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| ChemSpiderID = 145859 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 46736 |
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| ChEBI = 46736 |
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| Gmelin = 200290 |
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| Gmelin = 200290 |
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| SMILES = OOO |
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| SMILES = OOO |
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| StdInChI = 1S/H2O3/c1-3-2/h1-2H |
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| StdInChI = 1S/H2O3/c1-3-2/h1-2H |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/H2O3/c1-3-2/h1-2H |
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| InChI = 1/H2O3/c1-3-2/h1-2H |
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| StdInChIKey = JSPLKZUTYZBBKA-UHFFFAOYSA-N |
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| StdInChIKey = JSPLKZUTYZBBKA-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = JSPLKZUTYZBBKA-UHFFFAOYAV}} |
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| InChIKey = JSPLKZUTYZBBKA-UHFFFAOYAV}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| H = 2 |
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| H=2 | O=3 |
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| O = 3 |
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| ExactMass = 50.000393930 g mol<sup>-1</sup>}} |
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|Section8={{Chembox Related |
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| OtherCompounds = ]; ]; ] |
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'''Trioxidane''' (systematically named '''dihydrogen trioxide''',<ref name=Nyffeler-2004/><ref name=Plesnicar-2005/>), also called '''hydrogen trioxide'''<ref name=Cerkovnik-2013/><ref name=Strle-AngewChemIntEd-2015/> is an ] with the ] {{Chem|H|3|H}} (can be written as {{Chem|}} or {{Chem|}}). It is one of the unstable ]s.<ref name=Cerkovnik-2013>{{cite journal |last1=Cerkovnik |first1=J. |last2=Plesničar |first2=B. |title=Recent Advances in the Chemistry of Hydrogen Trioxide (HOOOH) |journal=] |volume=113 |pages=7930–7951|year=2013 |issue=10 |doi=10.1021/cr300512s|pmid=23808683}}</ref> In aqueous solutions, trioxidane decomposes to form water and ]: |
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] |
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The reverse reaction, the addition of singlet oxygen to water, typically does not occur in part due to the scarcity of singlet oxygen. In biological systems, however, ] is known to be generated from singlet oxygen, and the presumed mechanism is an antibody-catalyzed production of trioxidane from singlet oxygen.<ref name=Nyffeler-2004>{{cite journal |last1=Nyffeler |first1=P.T. |last2=Boyle |first2=N.A. |last3=Eltepu |first3=L. |last4=Wong |first4=C.-H. |last5=Eschenmoser |first5=A. |last6=Lerner |first6=R.A. |last7=Wentworth Jr. |first7=P. |title=Dihydrogen Trioxide (HOOOH) Is Generated during the Thermal Reaction between Hydrogen Peroxide and Ozone |journal=] |year=2004 |volume=43 |issue=35 |pages=4656–4659 |doi=10.1002/anie.200460457 |pmid=15317003}}</ref> |
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==Preparation== |
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Trioxidane can be obtained in small, but detectable, amounts in reactions of ] and ], or by the ]. Larger quantities have been prepared by the reaction of ozone with organic ]s at low temperatures in a variety of organic solvents, such as the ]. It is also formed during the decomposition of organic hydrotrioxides (ROOOH).<ref name=Plesnicar-2005>{{cite journal |last=Plesničar |first=B. |title=Progress in the Chemistry of Dihydrogen Trioxide (HOOOH) |journal=] |year=2005 |volume=52 |pages=1–12 |url = http://acta-arhiv.chem-soc.si/52/52-1-1.pdf}}</ref> Alternatively, trioxidane can be prepared by reduction of ozone with ] at low temperature. Using a resin-bound version of the latter, relatively pure trioxidane can be isolated as a solution in organic solvent. Preparation of high purity solutions is possible using the ] catalyst.<ref name=Strle-AngewChemIntEd-2015>{{citation |author1=Strle, G. |author2=Cerkovnik, J. |journal=] |title=A Simple and Efficient Preparation of High-Purity Hydrogen Trioxide (HOOOH) |year=2015 |volume=54 |issue=34 |pages=9917–9920 |doi=10.1002/anie.201504084 |pmid=26234421}}</ref> In acetone-''d''<sub>6</sub> at −20 °C, the characteristic <sup>1</sup>H NMR signal of trioxidane could be observed at a ] of 13.1 ppm.<ref name=Plesnicar-2005/> Solutions of hydrogen trioxide in diethyl ether can be safely stored at −20 °C for as long as a week.<ref name="Strle-AngewChemIntEd-2015" /> |
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The reaction of ozone with hydrogen peroxide is known as the "peroxone process". This mixture has been used for some time for treating groundwater contaminated with organic compounds. The reaction produces H<sub>2</sub>O<sub>3</sub> and H<sub>2</sub>O<sub>5</sub>.<ref name=Xu-2002>{{cite journal |last1=Xu |first1=X.|last2=Goddard |first2=W.A. |title=Nonlinear partial differential equations and applications: Peroxone chemistry: Formation of H<sub>2</sub>O<sub>3</sub> and ring-(HO<sub>2</sub>)(HO<sub>3</sub>) from O<sub>3</sub>/H<sub>2</sub>O<sub>2</sub> |journal=] |volume=99 |pages=15308–15312 |year=2002 |issue=24|pmc=137712 |pmid=12438699 |doi=10.1073/pnas.202596799|doi-access=free}}</ref> |
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==Structure== |
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In 1970-75, ] et al. observed ] and ] of dilute aqueous solutions of trioxidane.<ref name=Cerkovnik-2013/> In 2005, trioxidane was observed experimentally by ] in a supersonic jet. The molecule exists in a skewed structure, with an oxygen–oxygen–oxygen–hydrogen ] of 81.8°. The oxygen–oxygen ]s of 142.8 ] are slightly shorter than the 146.4 pm oxygen–oxygen bonds in ].<ref name=Suma-2005>{{cite journal |author1=Suma, K. |author2=Sumiyoshi, Y. |author3=Endo, Y. |title=The Rotational Spectrum and Structure of HOOOH |journal=] |year=2005 |volume=127 |issue=43 |pmid=16248618 |pages=14998–14999 |doi=10.1021/ja0556530}}</ref> Various dimeric and trimeric forms also seem to exist. |
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There is a trend of increasing ] and corresponding p''K''<sub>a</sub> as the number of oxygen atoms in the chain increases in HO<sub>''n''</sub>H structures (''n''=1,2,3).<ref>{{cite journal |title= Progress in the Chemistry of Dihydrogen Trioxide (HOOOH) |first= Božo |last= Plesničar |journal= Acta Chim. Slov. |year= 2005 |volume= 52 |pages= 1–12 |url= http://acta-arhiv.chem-soc.si/52/52-1-1.pdf }}</ref> |
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==Reactions== |
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Trioxidane readily decomposes into water and singlet oxygen, with a half-life of about 16 minutes in organic solvents at room temperature, but only milliseconds in water. It reacts with organic sulfides to form ]s, but little else is known of its reactivity. |
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Recent research found that trioxidane is the active ingredient responsible for the ] properties of the well known ]/] mix. Because these two compounds are present in biological systems as well it is argued that an ] in the human body can generate trioxidane as a powerful ] against invading bacteria.<ref name=Nyffeler-2004 /><ref>, ''News & Views'', September 13, 2004</ref> The source of the compound in biological systems is the reaction between singlet oxygen and water (which proceeds in either direction, of course, according to concentrations), with the singlet oxygen being produced by immune cells.<ref name=Plesnicar-2005/><ref name=Hoffmann-2004>{{cite journal |author=Hoffmann, R. |title=The Story of O |journal=] |year=2004 |volume=92 |pages=23 |url=https://roaldhoffmann.com/sites/default/files/fromd6/story_of_o.pdf}}</ref> |
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] predicts that more oxygen chain molecules or hydrogen polyoxides exist and that even indefinitely long oxygen chains can exist in a low-temperature gas. With this spectroscopic evidence a search for these type of molecules can start in ].<ref name=Suma-2005 /> A 2022 publication suggested the possibility of the presence of detectable concentrations of polyoxides in the atmosphere.<ref>{{Cite news|title=Hydrotrioxide (ROOOH) formation in the atmosphere|url=https://www.science.org/doi/10.1126/science.abn6012|work=Science|date=2022-05-27|accessdate=2022-05-27|issn=0036-8075|doi=10.1126/science.abn6012|pages=979–982|volume=376|issue=6596|language=en|first1=Torsten|last1=Berndt|first2=Jing|last2=Chen|first3=Eva R.|last3=Kjærgaard|first4=Kristian H.|last4=Møller|first5=Andreas|last5=Tilgner|first6=Erik H.|last6=Hoffmann|first7=Hartmut|last7=Herrmann|first8=John D.|last8=Crounse|first9=Paul O.|last9=Wennberg}}</ref> |
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==See also== |
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* ] |
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==References== |
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{{Reflist}} |
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{{Hydrogen compounds}} |
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{{Hydrides by group}} |
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] |
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] |
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] |
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] |