Oxirene: Difference between revisions

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| verifiedrevid = 416814959

| ImageFileL1=oxiren.png

| ImageSizeL1=80px

| ImageFileR1=oxirene structure.png

| ImageSizeR1=120px

| ImageFile2=Oxirene-3D-vdW.png

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| PIN=Oxirene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 146 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>

| SystematicName=Oxacyclopropene

| OtherNames=Epoxyethene<br />Ethyne oxide<br />Acetylene oxide

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=157-18-6

| PubChem=160438

| SMILES=C1=CO1

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 140985

| InChI = 1/C2H2O/c1-2-3-1/h1-2H

| InChIKey = BJEYNNFDAPPGST-UHFFFAOYAU

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C2H2O/c1-2-3-1/h1-2H

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = BJEYNNFDAPPGST-UHFFFAOYSA-N

| RTECS =

| MeSHName = C012469

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 30973

| Formula=C₂H₂O

| MolarMass=42.04 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

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| FlashPt=

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|Section8={{Chembox Related

| OtherFunction = [[Ethylene oxide]] [[cyclopropane]] [[cyclopropene]] [[aziridine]] [[thiirane]] [[thiirene]]

| OtherFunction_label = molecules with 3-membered rings

| OtherCompounds =

'''Oxirene''' is a [[heterocyclic compound|heterocyclic]] chemical compound which contains an [[Saturated and unsaturated compounds|unsaturated]] three-membered ring containing two carbon atoms and one oxygen atom. The molecule was synthesized in low temperature ices and detected upon sublimation by isomer selective photoionization [[time-of-flight mass spectrometry#Reflectron TOF|reflectron time-of-flight mass spectrometry]].<ref>{{Cite journal|last1=Wang|first1=Jia|last2=Marks|first2=Joshua|last3=Turner|first3=Andrew|last4=Mebel|first4=Alexander|last5=Eckhardt|first5=Andre|last6=Kaiser|first6=Ralf|date=March 2023|title=Gas-phase detection of oxirene|journal=Science Advances|language=en|volume=9|issue=10 |pages=eadg1134|doi=10.1126/sciadv.adg1134 |pmid=36897943 |pmc=10005165 |bibcode=2023SciA....9G1134W }}</ref>

[[Quantum chemistry|Quantum chemical]] computational techniques found the configuration to be extremely strained and proposed an [[Antiaromaticity|antiaromatic]] 4π electron system, as such oxirene is expected to be very high energy.<ref>{{cite journal | doi = 10.1016/S0166-1280(03)00198-2 | title = Assessment of density functional theory for the prediction of the nature of the oxirene stationary point | year = 2003 | last1 = Mawhinney | first1 = Robert C | last2 = Goddard | first2 = John D | journal = Journal of Molecular Structure: THEOCHEM | volume = 629 | issue = 1–3 | pages = 263–270}}</ref><ref>{{Cite book|title=Computational Chemistry - Introduction to the Theory and Applications of Molecular and Quantum Mechanics|first=Errol G.|last=Lewars|publisher=Springer|year=2011|edition=2nd|isbn=978-90-481-3862-3|doi=10.1007/978-90-481-3862-3|language=en}}</ref>

Experimental indications exist that substituted oxirenes (as intermediates or transition states) may be involved in carbonylcarbene rearrangements observed in the [[Wolff rearrangement]].<ref>{{Cite journal|title=100 Years of the Wolff Rearrangement|journal=European Journal of Organic Chemistry|volume=2002|issue=14|year=2002|pages=2193–2256|first=Wolfgang|last=Kirmse|doi=10.1002/1099-0690(200207)2002:14<2193::AID-EJOC2193>3.0.CO;2-D}}</ref> Computational evidence also point to the intermediacy of oxirenes in the ozonolysis of alkynes.<ref>{{Cite journal|last1=Cremer|first1=Dieter|last2=Crehuet|first2=Ramon|last3=Anglada|first3=Josep|date=June 2001|title=The Ozonolysis of AcetyleneA Quantum Chemical Investigation|journal=Journal of the American Chemical Society|language=en|volume=123|issue=25|pages=6127–6141|doi=10.1021/ja010166f|pmid=11414847|issn=0002-7863}}</ref>

==References==

{{Reflist}}

[[Category:Three-membered rings]]

[[Category:Antiaromatic compounds]]