Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
^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.
A silabenzene is a heteroaromatic compound containing one or more silicon atoms instead of carbon atoms in benzene. A single substitution gives silabenzene...
often be handled under air without risk of decomposition). In contrast, silabenzene, a related heavy-element analogue of benzene, is not only air- and moisture-sensitive...
aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene...
boratabenzene anion, i.e., it has the character C5H5B−-N+C5H5. borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene...
carbon. By comparison, compounds containing silene double bonds (such as silabenzene, an unstable analogue of benzene) exhibit far lower stability than the...
6-membered aromatic rings with one carbon replaced by another group: silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene...
aromatic rings with one carbon replaced by another element: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene...
When carbon in benzene is replaced by other elements in borabenzene, silabenzene, germanabenzene, stannabenzene, phosphorine or pyrylium salts the aromaticity...
alkylidenesilanes) are laboratory curiosities such as the silicon benzene analogue silabenzene. In 1967, Gusel'nikov and Flowers provided the first evidence for silenes...
representatives silabenzene and stannabenzene. 6-membered aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene...
in benzene is "replaced" by other elements, e.g., as in borabenzene, silabenzene, germanabenzene, stannabenzene, and phosphorine, aromaticity is retained...
aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene...
aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene...
aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene...
aromatic rings with one carbon replaced by another group:borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene...
aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene...
aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene...
aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene...