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An intermolecular Lewis pair based on tin acid and phosphonium ylide base functions

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Published/Copyright: January 13, 2025
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 79 Issue 12

Abstract

The tin-containing Lewis acid group (C2F5)3Sn was combined with a phosphonium ylide as base function in one molecule: o-[(C2F5)3Sn]-C6H4(Ph)2PCMe2. It was prepared by reacting the ortho-lithiated triphenylphosphoniumdimethylmethylide (o-Li-C6H4)(Ph)2PCMe2 with the stannyl chloride (C2F5)3SnCl to afford o-[(C2F5)3Sn]-C6H4(Ph)2PCMe2 in 86 % yield. It forms a ring structure with a bond between tin and the ylidic carbon atom both in solution and in the solid state and can thus be considered as a hidden frustrated Lewis pair. The title compound is unreactive towards H2, CO2, CS2, PhNCO and decomposes in the presence of SO2 or NH3. However, it is active in the catalytic reduction of CO2 with pinacolborane, H–BPin. The title compound reacts slowly with H–BPin in an unselective reaction from which a reduction product with cleaved C2F5 group, the phosphonium stannate (II) o-[(C2F5)2Sn]-C6H4(Ph)2PCHMe2, could be obtained in small amounts.

Keywords: phosphonium ylide; tin; Lewis acid; Lewis pair; catalysis

Dedicated to Professor Dr. Dr. h. c. Hubert Schmidbaur on the Occasion of his 90th Birthday.

Corresponding author: Norbert W. Mitzel, Chair of Inorganic and Structural Chemistry, Bielefeld University, Universitätsstraße 25, D-33615 Bielefeld, Germany, E-mail:

Funding source: Deutsche Forschungsgemeinschaft

Award Identifier / Grant number: grant MI 477/44-1, project number 461833739

Acknowledgments

The authors thank Marco Wißbrock for recording NMR spectra and Barbara Teichner for performing elemental analyses.

  1. Research ethics: Not applicable.

  2. Informed consent: Not applicable.

  3. Author contributions: All authors have accepted responsibility for the entire content of this manuscript and approved its submission.

  4. Use of Large Language Models, AI and Machine Learning Tools: None declared.

  5. Conflict of interest: The authors state no conflict of interest.

  6. Research funding: This work was funded by the Deutsche Forschungs­gemein­schaft (DFG, German Research Foundation, grant MI 477/44-1, project number 461833739).

  7. Data availability: Not applicable.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/znb-2024-0084).

Received: 2024-09-27
Accepted: 2024-10-02
Published Online: 2025-01-13
Published in Print: 2024-12-17

© 2024 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Preface
  4. Hubert Schmidbaur 90 years – an appreciation
  5. Reviews
  6. ‘Schmidbaur gold chemistry’ and beyond
  7. The ligand polyhedral model and its application to the structures and fluxional behaviour of the metal carbonyls
  8. Research Articles
  9. Equiatomic transition metal (T) silicides TT′Si: systematics of 29Si NMR Knight shifts
  10. New alkaline earth and rare earth representatives adopting the Ce2Al16Pt9-type structure
  11. Bis(2-chloroethyl)sulfane revisited: (ClH4C2)2S⋯S(C2H4Cl) dimers by S⋯S interaction in the solid state
  12. Structural studies of (2R,3R)-(+)-bis(diphenylphosphino)butane and (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl
  13. High-pressure synthesis and crystal structure of Al3BO6
  14. LiEu[BO3]: a lithium europium(II) ortho-oxoborate with a familiar crystal structure
  15. Fluorescence analysis of wood chips and their constituents
  16. C–S–H–PCE nanocomposites as hydration accelerator in calcined clay-limestone-blended low carbon cement
  17. An intermolecular Lewis pair based on tin acid and phosphonium ylide base functions
  18. Cyanopyridine adducts of SiF4 and SiCl4
  19. A [Zn4O(fcCO2)6] oxocarboxylate cluster: synthesis, chemical and physical properties
  20. Homo- and heteronuclear complexes derived from N-picoline-functionalized benzimidazolin-2-ylidene ligands
  21. “Coordination caps” of graded electron-donor capacity
  22. The hare and the hedgehog – Similar thermal expansion of argento- and aurophilic contacts for different reasons
  23. Atomic migration and phase transformation processes in dental amalgams over 27 years, monitored by X-ray spectroscopy and X-ray powder diffraction
  24. Book Review
  25. Hubert Schmidbaur: From Chemical Craftsmanship to the Art of Gilding Atoms. (Lives in Chemistry.)
https://doi.org/10.1515/znb-2024-0084
Keywords for this article
phosphonium ylide; tin; Lewis acid; Lewis pair; catalysis

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Preface
  4. Hubert Schmidbaur 90 years – an appreciation
  5. Reviews
  6. ‘Schmidbaur gold chemistry’ and beyond
  7. The ligand polyhedral model and its application to the structures and fluxional behaviour of the metal carbonyls
  8. Research Articles
  9. Equiatomic transition metal (T) silicides TT′Si: systematics of 29Si NMR Knight shifts
  10. New alkaline earth and rare earth representatives adopting the Ce2Al16Pt9-type structure
  11. Bis(2-chloroethyl)sulfane revisited: (ClH4C2)2S⋯S(C2H4Cl) dimers by S⋯S interaction in the solid state
  12. Structural studies of (2R,3R)-(+)-bis(diphenylphosphino)butane and (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl
  13. High-pressure synthesis and crystal structure of Al3BO6
  14. LiEu[BO3]: a lithium europium(II) ortho-oxoborate with a familiar crystal structure
  15. Fluorescence analysis of wood chips and their constituents
  16. C–S–H–PCE nanocomposites as hydration accelerator in calcined clay-limestone-blended low carbon cement
  17. An intermolecular Lewis pair based on tin acid and phosphonium ylide base functions
  18. Cyanopyridine adducts of SiF4 and SiCl4
  19. A [Zn4O(fcCO2)6] oxocarboxylate cluster: synthesis, chemical and physical properties
  20. Homo- and heteronuclear complexes derived from N-picoline-functionalized benzimidazolin-2-ylidene ligands
  21. “Coordination caps” of graded electron-donor capacity
  22. The hare and the hedgehog – Similar thermal expansion of argento- and aurophilic contacts for different reasons
  23. Atomic migration and phase transformation processes in dental amalgams over 27 years, monitored by X-ray spectroscopy and X-ray powder diffraction
  24. Book Review
  25. Hubert Schmidbaur: From Chemical Craftsmanship to the Art of Gilding Atoms. (Lives in Chemistry.)
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