Substituent effects on the structure and aromaticity of 4-silatriafulvene

T. Veszprémi, Masae Takahashi, Balazs Hajgató, Jun Ogasawara, Kenkichi Sakamoto, Mitsuo Kira

Research output: Article

35 Citations (Scopus)

Abstract

The structure and aromaticity of several 4-silatriafulvene derivatives are studied using correlated ab initio MO calculations. Electronegative substituents on silicon have been found to stabilize a nonplanar structure around the formal Si=C double bond, while π-electron acceptors planarize the molecule. To assess the aromaticity, the geometry index ΣCC, the nucleus-independent chemical shift (NICS), and the Bird indices are employed. Appropriate substituents on 4-silatriafulvene to enhance the aromatic character have been shown to cause the significant decrease of the Si=C π-bond strength. In cyclopropenylidene-1-silacyclopentadiene derivatives, both the three- and five-membered rings have low aromaticity, irrespective of the pyramidality of the molecular skeleton. Remarkably high aromaticity of the three-membered rings have been found in cyclopropenylidene-2-silaallene and 1-cyclopropenylidene-S-cyclopentadienylidene-2-silaallene.

Original languageEnglish
Pages (from-to)10530-10535
Number of pages6
JournalJournal of Physical Chemistry A
Volume102
Issue number51
Publication statusPublished - dec. 17 1998

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birds
rings
musculoskeletal system
Derivatives
chemical equilibrium
Birds
Chemical shift
Silicon
nuclei
causes
silicon
geometry
molecules
Molecules
electrons
Geometry
Electrons
cyclopropenylidene

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Veszprémi, T., Takahashi, M., Hajgató, B., Ogasawara, J., Sakamoto, K., & Kira, M. (1998). Substituent effects on the structure and aromaticity of 4-silatriafulvene. Journal of Physical Chemistry A, 102(51), 10530-10535.

Substituent effects on the structure and aromaticity of 4-silatriafulvene. / Veszprémi, T.; Takahashi, Masae; Hajgató, Balazs; Ogasawara, Jun; Sakamoto, Kenkichi; Kira, Mitsuo.

In: Journal of Physical Chemistry A, Vol. 102, No. 51, 17.12.1998, p. 10530-10535.

Research output: Article

Veszprémi, T, Takahashi, M, Hajgató, B, Ogasawara, J, Sakamoto, K & Kira, M 1998, 'Substituent effects on the structure and aromaticity of 4-silatriafulvene', Journal of Physical Chemistry A, vol. 102, no. 51, pp. 10530-10535.
Veszprémi T, Takahashi M, Hajgató B, Ogasawara J, Sakamoto K, Kira M. Substituent effects on the structure and aromaticity of 4-silatriafulvene. Journal of Physical Chemistry A. 1998 dec. 17;102(51):10530-10535.
Veszprémi, T. ; Takahashi, Masae ; Hajgató, Balazs ; Ogasawara, Jun ; Sakamoto, Kenkichi ; Kira, Mitsuo. / Substituent effects on the structure and aromaticity of 4-silatriafulvene. In: Journal of Physical Chemistry A. 1998 ; Vol. 102, No. 51. pp. 10530-10535.
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