Germabenzene

Germabenzene
Names
	Preferred IUPAC name Germine
	Other names Germanabenzene; Germin; Germanin
Identifiers
CAS Number	75920-32-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	16739132 ;
PubChem CID	20056561;
CompTox Dashboard (EPA)	DTXSID00560194 ;
	InChI InChI=1S/C5H6Ge/c1-2-4-6-5-3-1/h1-6H Key: ISOSVXOWIXXPIQ-UHFFFAOYSA-N ;
	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). verify (what is ?) Infobox references

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.

^ 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.
^ 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. PMID 12059214.
^ 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.

[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. PMID 12059214.

[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.

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