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{{Short description|Ion}} |
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{{Orphan|date=January 2011}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 444380239 |
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| verifiedrevid = 455176045 |
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| ImageFileL1 = Fluoronium-dimensions-2D.png |
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| ImageFile1 = Fluoronium-dimensions-2D.png |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeL1 = 121 |
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| ImageSize1 = 180 |
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| ImageNameL1 = Skeletal formula of fluoronium with assorted dimensions{{Citation|last = Diercksen|first = G. H. F.|last2 = von Niessen|first2 = W.|last3 = Kraemer|first3 = W. P.|title = SCF LCGO MO studies on the fluoronium ion FH<sub>2</sub><sup>+</sup> and its hydrogen bonding interaction with hydrogen fluoride FH|journal= Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta)|volume = 31|issue = 3|pages = 205–214|date = September|year = 1973|url = http://www.springerlink.com/content/v517wg14w47676r4/|doi = 10.1007/BF00526510}} |
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| ImageName1 = Skeletal formula of fluoronium with assorted dimensions{{Citation|last1 = Diercksen|first1 = G. H. F.|last2 = von Niessen|first2 = W.|last3 = Kraemer|first3 = W. P.|title = SCF LCGO MO studies on the fluoronium ion {{chem|FH|2|+}} and its hydrogen bonding interaction with hydrogen fluoride FH|journal= Theoretical Chemistry Accounts: Theory, Computation, and Modeling|volume = 31|issue = 3|pages = 205–214|date = September 1973|doi = 10.1007/BF00526510|s2cid = 98637994}} |
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| ImageFileL1 = Fluoronium-3D-balls.png |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeL1 = 131 |
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| ImageNameL1 = Ball-and-stick model of fluoronium |
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| ImageFileR1 = Fluoronium-3D-vdW.png |
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| ImageFileR1 = Fluoronium-3D-vdW.png |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeR1 = 121 |
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| ImageSizeR1 = 131 |
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| ImageNameR1 = Spacefill model of fluoronium |
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| ImageNameR1 = Spacefill model of fluoronium |
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| IUPACName = Fluoronium |
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| IUPACName = Fluoronium |
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| SystematicName = Fluoranium |
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| SystematicName = Fluoranium<ref>{{Cite web|title = Fluoronium (CHEBI:50314)|url = https://www.ebi.ac.uk/chebi/searchId.do?chebiId=50314|work = Chemical Entities of Biological Interest (ChEBI)|location = UK|publisher = European Bioinformatics Institute}}</ref> |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 12206-67-6 |
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| ChemSpiderID = 19122106 |
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| CASNo_Ref = {{Cascite|changed|CAS}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 19122106 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 50314 |
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| ChEBI = 50314 |
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| SMILES = |
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| SMILES = |
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| StdInChI = 1S/FH2/h1H2/q+1 |
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| StdInChI = 1S/FH2/h1H2/q+1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/FH2/h1H2/q+1 |
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| InChI = 1/FH2/h1H2/q+1 |
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| StdInChIKey = YNESUKSMQODWNS-UHFFFAOYSA-N |
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| StdInChIKey = YNESUKSMQODWNS-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 = YNESUKSMQODWNS-UHFFFAOYAK |
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| InChIKey = YNESUKSMQODWNS-UHFFFAOYAK |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = H<sub>2</sub>F<sup>+</sup> |
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| Formula = H<sub>2</sub>F<sup>+</sup> |
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| ConjugateBase = ] |
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| MolarMass = 21.01428 g mol<sup>-1</sup> |
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| ExactMass = 21.014053269 g mol<sup>-1</sup> |
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| MolarMass = 21.01374 g mol<sup>−1</sup> |
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}} |
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The '''fluoronium''' ion is an ] ] with the ] {{Chem|H|2|F|+}}. It is one of the cations found in ].<ref>{{Cite journal|last1=Esteves|first1=Pierre M.|last2=Ramírez-Solís|first2=Alejandro|last3=Mota|first3=Claudio J. A.|date=March 2002|title=The Nature of Superacid Electrophilic Species in HF/SbF5: A Density Functional Theory Study|journal=Journal of the American Chemical Society|volume=124|issue=11|pages=2672–2677|doi=10.1021/ja011151k|issn=0002-7863|pmid=11890818}}</ref> The structure of the salt with the {{Chem|Sb|2|F|11|-}} anion, has been determined.<ref>{{cite journal|last1=Mootz|first1=Dietrich|last2=Bartmann|first2=Klemens|date=1988|title=The Fluoronium Ions H<sub>2</sub>F<sup>+</sup> and {{chem|H|3|F|2|+}}: Characterization by Crystal Structure Analysis|url=|journal=Angewandte Chemie|volume=27|issue=3|pages=391–392|doi=10.1002/anie.198803911}}</ref><ref>{{Cite journal|last1 = Diercksen|first1 = G. H. F.|last2 = von Niessen|first2 = W.|last3 = Kraemer|first3 = W. P.|title = SCF LCGO MO studies on the fluoronium ion {{chem|FH|2|+}} and its hydrogen bonding interaction with hydrogen fluoride FH|journal= Theoretical Chemistry Accounts: Theory, Computation, and Modeling|volume = 31|issue = 3|pages = 205–214|date = 1973|doi = 10.1007/BF00526510|s2cid = 98637994}}</ref> The fluoronium ion is ] with the ] molecule and the ]. |
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The '''fluoronium''' ], H<sub>2</sub>F<sup>+</sup>, is a ] formed by ] or self-ionic dissociation of ]: |
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The term can also refer to organyl substituted species of type H–{{overset|+|F}}–R, R–{{overset|+|F}}–R, or R<sub>2</sub>C=F<sup>+</sup>. In contrast to the heavier halogens, which have long been known to form open-chain ]s (such as <sup>+</sup><sup>–</sup>)<ref>{{Cite journal|last1=Hämmerling|first1=Sebastian|last2=Thiele|first2=Günther|last3=Steinhauer|first3=Simon|last4=Beckers|first4=Helmut|last5=Müller|first5=Carsten|last6=Riedel|first6=Sebastian|date=2019|title=A Very Strong Methylation Agent: |url=https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201904007|journal=Angewandte Chemie International Edition|language=en|volume=58|issue=29|pages=9807–9810|doi=10.1002/anie.201904007|pmid=31050103 |s2cid=143434865 |issn=1521-3773}}</ref> as well as cyclic haliranium ions, fluorine was not believed to form fluoronium ions of type R–{{overset|+|F}}–R until the recent characterization of a fluoronium ion locked in a designed cage structure by Lectka and coworkers.<ref>{{Cite journal|last1=Pitts|first1=Cody Ross|last2=Holl|first2=Maxwell Gargiulo|last3=Lectka|first3=Thomas|date=2018-02-12|title=Spectroscopic Characterization of a <sup>+</sup> Fluoronium Ion in Solution|journal=Angewandte Chemie International Edition|language=en|volume=57|issue=7|pages=1924–1927|doi=10.1002/anie.201712021|pmid=29316122|doi-access=}}</ref> Recent solvolysis experiments and NMR spectroscopic studies on a metastable <sup>+</sup> fluoronium ion strongly support the ] fluoronium structure over the alternative rapidly equilibrating classical carbocation. Definitive structural proof of the symmetrical <sup>+</sup> was reported by Riedel, Lectka, and coworkers by single crystal X-ray diffraction analysis. Besides its synthesis and crystallographic characterization as the <sup>−</sup> salt, vibrational spectra could be recorded and a detailed analysis concerning the nature of the bonding situation in this fluoronium ion and its heavier halonium homologues was reported.<ref>{{Cite journal|last1=Hoffmann|first1=Kurt F.|last2=Wiesner|first2=Anja|last3=Müller|first3=Carsten|last4=Steinhauer|first4=Simon|last5=Beckers|first5=Helmut|last6=Kazim|first6=Muhammad|last7=Pitts|first7=Cody Ross|last8=Lectka|first8=Thomas|last9=Riedel|first9=Sebastian|date=2021-09-06|title=Structural proof of a + fluoronium cation|journal=Nature Communications|language=en|volume=12|issue=1|pages=5275|doi=10.1038/s41467-021-25592-6|pmid=34489464 |pmc=8421340 |issn=2041-1723}}</ref> |
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:HF + H<sup>+</sup> → H<sub>2</sub>F<sup>+</sup> |
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or |
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:3HF {{unicode|⇌}} H<sub>2</sub>F<sup>+</sup> + ] |
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Unlike for ]s based on ], ] or ] (chloronium, H<sub>2</sub>Cl<sup>+</sup>, bromonium, H<sub>2</sub>Br<sup>+</sup>, iodonium, H<sub>2</sub>I<sup>+</sup>), hydrocarbyl derivatives of fluoronium, i.e. R<sub>2</sub>F<sup>+</sup>, remain unknown. |
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== References == |
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== References == |
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