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Structural characterization and reactivity of a room-temperature-stable, antiaromatic cyclopentadienyl cation salt

Nature Chemistry volume 16, pages 651–657 (2024)Cite this article

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Abstract

The singlet states of cyclopentadienyl (Cp) cations are considered as true prototypes of an antiaromatic system. Unfortunately, their high intrinsic reactivity inhibited their isolation in the solid state as a salt, and controlled reactions are also scarce. Here we present the synthesis and solid state structure of the room-temperature-stable Cp cation salt [Cp(C6F5)5]+[Sb3F16]−. Although the aromatic triplet state of the [Cp(C6F5)5]+ cation is energetically favoured in the gas phase according to quantum chemical calculations, coordination of the cation by either [Sb3F16]− or C6F6 in the crystal lattice stabilizes the antiaromatic singlet state, which is present in the solid state. The calculated hydride and fluoride ion affinities of the [Cp(C6F5)5]+ cation are higher than those of the perfluorinated tritylium cation [C(C6F5)3]+. Reactions of [Cp(C6F5)5]+[Sb3F16]− with CO, which probably yields the corresponding carbonyl complex, and of radical Cp(C6F5)5∙ with selected model substrates (Cp2Fe, (Ph3C∙)2 and Cp*Al) are also presented.

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Fig. 1: Literature reports of cyclopentadienyl cations, synthesis of cation 1, radical 2 and their precursors A–D, and molecular structures of two different solvates of the Cp cation 1 (sc-XRD).
Fig. 2: Paramagnetic susceptibility data for 1a+[Sb3F16]−·1.5C6F6 and possible electronic states for a Cp cation.
Fig. 3: Reactions of 1+[Sb3F16]− and 2.

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Data availability

All data generated or analysed during this study are included in this published article (and its Supplementary Information files). The structures of B, C6(C6F5)6, 1a+, 1b+, 2a‒b, 3a‒c, 5 and 6 in the solid state were determined by single-crystal X-ray diffraction and the crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC) with identifiers 2246848 (1a+), 2246849 (1b+), 2246850 (2a), 2246851 (2b), 2246852 (3a), 2246853 (3b), 2246854 (3c), 2246857 (5), 2246858 (6), 2246859 (B) and 2246860 (C6(C6F5)6). Copies of the data can be obtained free of charge on application to the CCDC.

Code availability

DFT and double-hybrid DFT methods, as implemented in the quantum chemistry program packages Gaussian1676, Amsterdam Density Functional (ADF)77 and Orca 5.0.078, were used to calculate molecular geometries, orbital energies, charges, natural bond orbitals and NICS values. All data generated or analysed are included in the Supplementary Information file.

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Acknowledgements

S.S. acknowledges financial support from the Deutsche Forschungsgemeinschaft (DFG, grant INST 20876/282-1 FUGG) and the University of Duisburg-Essen. We thank B. Geoghegan and G.E. Cutsail III (MPI CEC, Mülheim an der Ruhr, Germany) for EPR measurements, M. Weinert for CV studies, T. Schaller, F. Niemeyer and B. Römer (University of Duisburg-Essen) for NMR measurements, and J. Haberhauer (Ruhr-Universität Bochum) for her help in quantum chemical calculations. M.M. and S.M.R. thank the DFG (German Research Foundation) for financial support (project ID 387284271, grant SFB 1349). D.J.S. and F.N. acknowledge the Max Planck Gesellschaft for funding.

Author information

Authors and Affiliations

  1. Institute of Inorganic Chemistry, University of Duisburg-Essen, Essen, Germany

    Yannick Schulte, Christoph Wölper & Stephan Schulz

  2. Institute of Inorganic Chemistry, Freie Universität Berlin, Berlin, Germany

    Susanne M. Rupf & Moritz Malischewski

  3. Max-Planck Institut für Kohlenforschung, Mülheim an der Ruhr, Germany

    Daniel J. SantaLucia & Frank Neese

  4. Institute of Organic Chemistry, University of Duisburg-Essen, Essen, Germany

    Gebhard Haberhauer

  5. Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Duisburg, Germany

    Stephan Schulz

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  1. Yannick Schulte
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Contributions

Y.S. was responsible for study conceptualization, investigation, validation, formal analysis, writing the original draft and visualization. C.W. conducted single-crystal X-ray analysis. S.M.R. and M.M. undertook cyclic voltammetry studies in liquid SO2. D.J.S. measured and interpreted the magnetic susceptibility data. F.N. undertook the SQUID study. G.H. wrote the original draft, reviewed and edited the manuscript, and was responsible for visualization and performing calculations. S.S. was responsible for study conceptualization, writing the original draft, manuscript review and editing, visualization, supervision and project administration.

Corresponding authors

Correspondence to Gebhard Haberhauer or Stephan Schulz.

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Nature Chemistry thanks Ingo Krossing, Yirong Mo and the other, anonymous, reviewer(s) for their contribution to the peer review of this work.

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Supplementary information

Supplementary Information

Experimental details, Supplementary Figs. 1–49, Tables 1–7, and calculated HIA and FIA.

Supplementary Data 1

Computational data: xyz files of all compounds calculated using different basis sets, and text files of calculated absolute energies, bonding energies, thermochemical data.

Supplementary Data 2

Crystallographic data for compound 1a; CCDC reference 2246848.

Supplementary Data 3

Crystallographic data for compound 1b; CCDC reference 2246849.

Supplementary Data 4

Crystallographic data for compound 2a; CCDC reference 2246850.

Supplementary Data 5

Crystallographic data for compound 2b; CCDC reference 2246851.

Supplementary Data 6

Crystallographic data for compound 3a; CCDC reference 2246852.

Supplementary Data 7

Crystallographic data for compound 3b; CCDC reference 2246853.

Supplementary Data 8

Crystallographic data for compound 3c; CCDC reference 2246854.

Supplementary Data 9

Crystallographic data for compound 5; CCDC reference 2246857.

Supplementary Data 10

Crystallographic data for compound 6; CCDC reference 2246858.

Supplementary Data 11

Crystallographic data for compound B; CCDC reference 2246859.

Supplementary Data 12

Crystallographic data for hexakispentafluorophenylbenzene; CCDC reference 2246860.

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Schulte, Y., Wölper, C., Rupf, S.M. et al. Structural characterization and reactivity of a room-temperature-stable, antiaromatic cyclopentadienyl cation salt. Nat. Chem. 16, 651–657 (2024). https://doi.org/10.1038/s41557-023-01417-5

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