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Are the Silacyclopentadienyl Anion and the Silacyclopropenyl Cation Aromatic?
Journal of the American Chemical Society (1983)
  • Mark S. Gordon
  • Philip Boudjouk
  • Freidun Anwari
Abstract

Stabilization energies attributable to aromaticity in the silacyclopentadienyl anion and the silacyclopropenyl cation were found to be small in the former and absent in the latter when calculated from bond-separation reactions employing 3-21G and ST0-2G basis sets. The silacyclopentadienyl anion is approximately 25% as aromatic as the all-carbon analogue whereas silabenzene is more than 80% as aromatic as benzene. The introduction of diffuse functions into the basis sets has only a small effect on these results. The silacyclopropenyl cation is actually destabilized but strain is probably a key factor in the comparison. Also found was that the ST0-2G basis set gives geometries and relative energies consistent with those of a larger basis set and that the semiempirical INDO method may be useful for predicting the structures of larger systems for which geometry optimizations even with ST0-2G may be too time consuming.

Disciplines
Publication Date
July, 1983
Publisher Statement
Reprinted (adapted) with permission from Journal of the American Chemical Society 105 (1983): 4972, doi:10.1021/ja00353a021. Copyright 1983 American Chemical Society.
Citation Information
Mark S. Gordon, Philip Boudjouk and Freidun Anwari. "Are the Silacyclopentadienyl Anion and the Silacyclopropenyl Cation Aromatic?" Journal of the American Chemical Society Vol. 105 Iss. 15 (1983)
Available at: http://works.bepress.com/mark_gordon/34/