Tris(trimethylsilyl)cyclopropenylmm cation: The first X-ray structure analysis of an α-silyl-substituted carbocation

Armin De Meijere, Dietmar Faber, Mathias Noltemeyer, Roland Boese, Thomas Haumann, Thomas Müller, Michael Bendikov, Eynatte Matzner, Yitzhak Apeloig

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16 Citations (Scopus)

Abstract

The X-ray crystal structure analysis of tris(trimethylsilyl)cyclopropenylium cation 2 is presented and compared with the structure and bonding properties obtained by quantum mechanical ab initio calculations. The calculated bond lengths for 2 are in good agreement with the experimentally determined ones. The effect of tris-silyl and tris-methyl substitution on the stability of the tris-substituted cyclopropenylium ions are calculated by using the isodesmic hydride transfer reaction 1. The pKR+ value of 2 is predicted to be 4.

Original languageEnglish
Pages (from-to)8564-8568
Number of pages5
JournalJournal of Organic Chemistry
Volume61
Issue number24
DOIs
Publication statusPublished - Nov 29 1996

ASJC Scopus subject areas

  • Organic Chemistry

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    De Meijere, A., Faber, D., Noltemeyer, M., Boese, R., Haumann, T., Müller, T., Bendikov, M., Matzner, E., & Apeloig, Y. (1996). Tris(trimethylsilyl)cyclopropenylmm cation: The first X-ray structure analysis of an α-silyl-substituted carbocation. Journal of Organic Chemistry, 61(24), 8564-8568. https://doi.org/10.1021/jo960478e