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Fluoronium

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Ion
Fluoronium
Ball-and-stick model of fluoronium
Ball-and-stick model of fluoronium
Spacefill model of fluoronium
Spacefill model of fluoronium
Names
IUPAC name Fluoronium
Systematic IUPAC name Fluoranium
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
CompTox Dashboard (EPA)
InChI
  • InChI=1S/FH2/h1H2/q+1Key: YNESUKSMQODWNS-UHFFFAOYSA-N
  • InChI=1/FH2/h1H2/q+1Key: YNESUKSMQODWNS-UHFFFAOYAK
SMILES
Properties
Chemical formula H2F
Molar mass 21.01374 g mol
Conjugate base Hydrogen fluoride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

The fluoronium ion is an inorganic cation with the chemical formula H
2F
. It is one of the cations found in fluoroantimonic acid. The structure of the salt with the Sb
2F
11 anion, has been determined. The fluoronium ion is isoelectronic with the water molecule and the azanide ion.

The term can also refer to organyl substituted species of type H–+F–R, R–+F–R, or R2C=F. In contrast to the heavier halogens, which have long been known to form open-chain halonium ions (such as ) as well as cyclic haliranium ions, fluorine was not believed to form fluoronium ions of type R–+F–R until the recent characterization of a fluoronium ion locked in a designed cage structure by Lectka and coworkers. Recent solvolysis experiments and NMR spectroscopic studies on a metastable fluoronium ion strongly support the dicoordinated fluoronium structure over the alternative rapidly equilibrating classical carbocation. Definitive structural proof of the symmetrical was reported by Riedel, Lectka, and coworkers by single crystal X-ray diffraction analysis. Besides its synthesis and crystallographic characterization as the 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.

References

A Cs-symmetrical fluoronium ion characterized by Lectka and coworkers
  1. Esteves, Pierre M.; Ramírez-Solís, Alejandro; Mota, Claudio J. A. (March 2002). "The Nature of Superacid Electrophilic Species in HF/SbF5: A Density Functional Theory Study". Journal of the American Chemical Society. 124 (11): 2672–2677. doi:10.1021/ja011151k. ISSN 0002-7863. PMID 11890818.
  2. Mootz, Dietrich; Bartmann, Klemens (1988). "The Fluoronium Ions H2F and H
    3F
    2: Characterization by Crystal Structure Analysis". Angewandte Chemie. 27 (3): 391–392. doi:10.1002/anie.198803911.
  3. Diercksen, G. H. F.; von Niessen, W.; Kraemer, W. P. (1973). "SCF LCGO MO studies on the fluoronium ion FH
    2 and its hydrogen bonding interaction with hydrogen fluoride FH". Theoretical Chemistry Accounts: Theory, Computation, and Modeling. 31 (3): 205–214. doi:10.1007/BF00526510. S2CID 98637994.
  4. Hämmerling, Sebastian; Thiele, Günther; Steinhauer, Simon; Beckers, Helmut; Müller, Carsten; Riedel, Sebastian (2019). "A Very Strong Methylation Agent: [Me2Cl][Al(OTeF5)4]". Angewandte Chemie International Edition. 58 (29): 9807–9810. doi:10.1002/anie.201904007. ISSN 1521-3773. PMID 31050103. S2CID 143434865.
  5. Pitts, Cody Ross; Holl, Maxwell Gargiulo; Lectka, Thomas (2018-02-12). "Spectroscopic Characterization of a Fluoronium Ion in Solution". Angewandte Chemie International Edition. 57 (7): 1924–1927. doi:10.1002/anie.201712021. PMID 29316122.
  6. Hoffmann, Kurt F.; Wiesner, Anja; Müller, Carsten; Steinhauer, Simon; Beckers, Helmut; Kazim, Muhammad; Pitts, Cody Ross; Lectka, Thomas; Riedel, Sebastian (2021-09-06). "Structural proof of a [C–F–C]+ fluoronium cation". Nature Communications. 12 (1): 5275. doi:10.1038/s41467-021-25592-6. ISSN 2041-1723. PMC 8421340. PMID 34489464.
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