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Fluoride Ion Chelation By a Bidentate Phosphonium/Borane Lewis Acid
Abstract
The phosphonium borane [1-Mes2B-2-MePh2P-(C6H4)]+ ([2]+) has been synthesized as an iodide salt by alkylation of 1-Mes2B-2-Ph2P-(C6H4) with MeI. This novel cationic borane complexes fluoride to afford the corresponding zwitterionic fluoroborate complex 1-FMes2B-2-MePh2P-(C6H4) (2-F) with a binding constant in MeOH exceeding that of 1-Mes2B-4-MePh2P-(C6H4) ([1]+) by at least 4 orders of magnitude. Structural and computational results indicate that the high fluorophilicity of [2]+ arises from both Coulombic and cooperative effects which lead to formation of a B-F-->P interaction with a F-->P distance of 2.666(2) A. These results, which are supported by NBO and AIM analyses, show that the latent phosphorus-centered Lewis acidity of the phosphonium moiety in [2]+ can be exploited to enhance fluoride binding via chelation.
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Cited by
Applications of Supramolecular Anion Recognition
Busschaert, N., Caltagirone, C., Van Rossom, W., & Gale, P. A. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00099 · Cited by 1,249
Recent developments in and perspectives on three-coordinate boron materials: a bright future
Ji, L., Griesbeck, S., & Marder, T. B. (2017) · Chemical Science · doi:10.1039/c6sc04245g · Cited by 733
Recognition and sensing of fluoride anion
Cametti, M., & Rissanen, K. (2009) · Chemical Communications · doi:10.1039/b902069a · Cited by 654
Kim, Y., & Gabbaï, F. P. (2009) · Journal of the American Chemical Society · doi:10.1021/ja8091467 · Cited by 260
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Metadata
- Authors
- Hudnall, T. W., Kim, Y.-M., Bebbington, M. W. P., Bourissou, D., & Gabbaï, F. P.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-07-25
- Volume
- 130
- Issue
- 33
- Pages
- 10890-10891
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2014200671
- Cited by
- 230
- References
- 0
- FWCI
- 11.55
- Type
- journal article
- Language
- en
- Open access
- closed
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