Germabenzene

Germabenzene (C₅H₆Ge) is the parent representative of a group of chemical compounds containing in their molecular structure a benzene ring with a carbon atom replaced by a germanium atom. Germabenzene itself has been studied theoretically,[1] and synthesized with a bulky 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl or Tbt group.[2] Also, stable naphthalene derivatives do exist in the laboratory such as the 2-germanaphthalene-containing substance represented below.[3] The germanium to carbon bond in this compound is shielded from potential reactants by a Tbt group. This compound is aromatic just as the other carbon group representatives silabenzene and stannabenzene.

A stable 2-germanaphthalene derivative

Germabenzene

Skeletal formula of germabenzene Ball-and-stick model of the germabenzene molecule
Names
Preferred IUPAC name Germine
Other names Germanabenzene; Germin; Germanin
Identifiers
CAS Number	75920-32-0^Y
3D model (JSmol)	Interactive image
ChemSpider	16739132^Y
CompTox Dashboard (EPA)	DTXSID00560194
InChI InChI=1S/C5H6Ge/c1-2-4-6-5-3-1/h1-6H^Y Key: ISOSVXOWIXXPIQ-UHFFFAOYSA-N^Y
SMILES [H][Ge]1C=CC=CC=1
Properties
Chemical formula	C5H6Ge
Molar mass	138.733 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

See also

• 6-membered aromatic rings with one carbon replaced by another group: borabenzene, benzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, pyrylium salt

References

1. Ebrahimi, A. A.; Ghiasi, R.; Foroutan-Nejad, C. (2010). "Topological Characteristics of the Ring Critical Points and the Aromaticity of Groups IIIa to VIa Hetero-Benzenes". Journal of Molecular Structure: THEOCHEM. 941 (1–3): 47–52. doi:10.1016/j.theochem.2009.10.038.
2. Nakata, Norio; Takeda, Nobuhiro; Tokitoh, Norihiro (2002-06-01). "Synthesis and Properties of the First Stable Germabenzene". Journal of the American Chemical Society. 124 (24): 6914–6920. doi:10.1021/ja0262941. ISSN 0002-7863.
3. Nakata, N.; Takeda, N.; Tokitoh, N. (2001). "Synthesis and Structure of a Kinetically Stabilized 2-Germanaphthalene: The First Stable Neutral Germaaromatic Compound". Organometallics. 20 (26): 5507–5509. doi:10.1021/om010881y.