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

Research output: Contribution to journalArticle

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
Publication statusPublished - Nov 29 1996

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Bond length
Hydrides
Cations
Substitution reactions
Crystal structure
Ions
X rays

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

De Meijere, A., Faber, D., Noltemeyer, M., Boese, R., Haumann, T., Müller, T., ... 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.

Tris(trimethylsilyl)cyclopropenylmm cation : The first X-ray structure analysis of an α-silyl-substituted carbocation. / De Meijere, Armin; Faber, Dietmar; Noltemeyer, Mathias; Boese, Roland; Haumann, Thomas; Müller, Thomas; Bendikov, Michael; Matzner, Eynatte; Apeloig, Yitzhak.

In: Journal of Organic Chemistry, Vol. 61, No. 24, 29.11.1996, p. 8564-8568.

Research output: Contribution to journalArticle

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, vol. 61, no. 24, pp. 8564-8568.
De Meijere A, Faber D, Noltemeyer M, Boese R, Haumann T, Müller T et al. Tris(trimethylsilyl)cyclopropenylmm cation: The first X-ray structure analysis of an α-silyl-substituted carbocation. Journal of Organic Chemistry. 1996 Nov 29;61(24):8564-8568.
De Meijere, Armin ; Faber, Dietmar ; Noltemeyer, Mathias ; Boese, Roland ; Haumann, Thomas ; Müller, Thomas ; Bendikov, Michael ; Matzner, Eynatte ; Apeloig, Yitzhak. / Tris(trimethylsilyl)cyclopropenylmm cation : The first X-ray structure analysis of an α-silyl-substituted carbocation. In: Journal of Organic Chemistry. 1996 ; Vol. 61, No. 24. pp. 8564-8568.
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