Silabenzene

Silabenzene
Structural formula of silabenzene
Ball-and-stick model of the Silabenzene molecule
Names
Preferred IUPAC name
Siline[1]
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H6Si/c1-2-4-6-5-3-1/h1-6H checkY
    Key: YJHHPIHPAJYNFT-UHFFFAOYSA-N checkY
  • InChI=1/C5H6Si/c1-2-4-6-5-3-1/h1-6H
    Key: YJHHPIHPAJYNFT-UHFFFAOYAP
  • C1=CC=[SiH]C=C1
Properties
C5H6Si
Molar mass 94.188 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Structures of some unstable silabenzenes

A silabenzene is a heteroaromatic compound containing one or more silicon atoms instead of carbon atoms in benzene. A single substitution gives silabenzene proper; additional substitutions give a disilabenzene (3 theoretical isomers), trisilabenzene (3 isomers), etc.

Silabenzenes have been the targets of many theoretical and synthetic studies by organic chemists interested in the question of whether analogs of benzene with Group IV elements heavier than carbon, e.g., silabenzene, stannabenzene and germabenzene—so-called "heavy benzenes"—exhibit aromaticity.

Although several heteroaromatic compounds bearing nitrogen, oxygen, and sulfur atoms have been known since the early stages of organic chemistry, silabenzene had been considered to be a transient, un-isolable compound and was detected only in low-temperature matrices or as its Diels-Alder adduct for a long time. In recent years, however, a kinetically stabilized silabenzene and other heavy aromatic compounds with silicon or germanium atoms have been reported.

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 392. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.