Substituent effects on the structure and aromaticity of 4-silatriafulvene

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

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36 Citations (Scopus)


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
Issue number51
Publication statusPublished - 1998 Dec 17
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry


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