Structural proof of a [C–F–C]+ fluoronium cation

Kurt F. Hoffmann, Anja Wiesner, Carsten Müller, Simon Steinhauer, Helmut Beckers, Muhammad Kazim, Cody Ross Pitts, Thomas Lectka () and Sebastian Riedel ()
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Kurt F. Hoffmann: Fachbereich Biologie, Chemie, Pharmazie, Institut für Chemie und Biochemie – Anorganische Chemie, Freie Universität Berlin
Anja Wiesner: Fachbereich Biologie, Chemie, Pharmazie, Institut für Chemie und Biochemie – Anorganische Chemie, Freie Universität Berlin
Carsten Müller: Fachbereich Biologie, Chemie, Pharmazie, Institut für Chemie und Biochemie – Anorganische Chemie, Freie Universität Berlin
Simon Steinhauer: Fachbereich Biologie, Chemie, Pharmazie, Institut für Chemie und Biochemie – Anorganische Chemie, Freie Universität Berlin
Helmut Beckers: Fachbereich Biologie, Chemie, Pharmazie, Institut für Chemie und Biochemie – Anorganische Chemie, Freie Universität Berlin
Muhammad Kazim: Johns Hopkins University
Cody Ross Pitts: Johns Hopkins University
Thomas Lectka: Johns Hopkins University
Sebastian Riedel: Fachbereich Biologie, Chemie, Pharmazie, Institut für Chemie und Biochemie – Anorganische Chemie, Freie Universität Berlin

Nature Communications, 2021, vol. 12, issue 1, 1-7

Abstract: Abstract Organic fluoronium ions can be described as positively charged molecules in which the most electronegative and least polarizable element fluorine engages in two partially covalent bonding interactions to two carbon centers. While recent solvolysis experiments and NMR spectroscopic studies on a metastable [C–F–C]+ fluoronium ion strongly support the divalent fluoronium structure over the alternative rapidly equilibrating classical carbocation, the model system has, to date, eluded crystallographic analysis to confirm this phenomenon in the solid state. Herein, we report the single crystal structure of a symmetrical [C–F–C]+ fluoronium cation. Besides its synthesis and crystallographic characterization as the [Sb2F11]− salt, vibrational spectra are discussed and a detailed analysis concerning the nature of the bonding situation in this fluoronium ion and its heavier halonium homologues is performed, which provides detailed insights on this molecular structure.

Date: 2021
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DOI: 10.1038/s41467-021-25592-6

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