Fluoronium: Difference between revisions

{{Short description|Ion}}

| Watchedfields = changed

| verifiedrevid = 455176045

| ImageFile1 = Fluoronium-dimensions-2D.png

| ImageFile1_Ref = {{chemboximage|correct|??}}

| ImageSize1 = 180

| 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}}

| ImageFileL1 = Fluoronium-3D-balls.png

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageSizeL1 = 131

| ImageNameL1 = Ball-and-stick model of fluoronium

| ImageFileR1_Ref = {{chemboximage|correct|??}}

| ImageSizeR1 = 131

| ImageNameR1 = Spacefill model of fluoronium

| SystematicName = Fluoranium

|Section1={{Chembox Identifiers

| CASNo = 12206-67-6

| CASNo_Ref = {{Cascite|changed|CAS}}

| ChemSpiderID = 19122106

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| SMILES = [FH2+]

| StdInChI = 1S/FH2/h1H2/q+1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| InChI = 1/FH2/h1H2/q+1

| StdInChIKey = YNESUKSMQODWNS-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey = YNESUKSMQODWNS-UHFFFAOYAK

|Section2={{Chembox Properties

| Formula = H₂F⁺

| ConjugateBase = [[Hydrogen fluoride]]

| MolarMass = 21.01374 g mol⁻¹

The '''fluoronium''' ion is an [[inorganic chemistry|inorganic]] [[ion#Anions and cations|cation]] with the [[chemical formula]] {{Chem|H|2|F|+}}. It is one of the cations found in [[fluoroantimonic acid]].<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 H₂F⁺ 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 [[isoelectronic]] with the [[Properties of water|water]] molecule and the [[Azanide|azanide ion]].

The term can also refer to organyl substituted species of type H–{{overset|+|F}}–R, R–{{overset|+|F}}–R, or R₂C=F⁺. In contrast to the heavier halogens, which have long been known to form open-chain [[halonium ion]]s (such as [Me₂Cl]⁺[Al(OTeF₅)₄]^–)<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: [Me2Cl][Al(OTeF5)4]|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 [C−F−C]⁺ 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 [C–F–C]⁺ fluoronium ion strongly support the [[Coordination number|dicoordinated]] fluoronium structure over the alternative rapidly equilibrating classical carbocation. Definitive structural proof of the symmetrical [C–F–C]⁺ was reported by Riedel, Lectka, and coworkers by single crystal X-ray diffraction analysis. Besides its synthesis and crystallographic characterization as the [Sb₂F₁₁]⁻ 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 [C–F–C]+ 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>

[[File:Lectka-fluoronium.png|thumb|A C_s-symmetrical fluoronium ion characterized by Lectka and coworkers]]

[[Category:Fluorine compounds]]

[[Category:Hydrogen compounds]]