Germabenzene (C
5H
6Ge) is the parent representative of a group of
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
s containing in their molecular structure a
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
ring with a
carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent
In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
atom replaced by a
germanium
Germanium is a chemical element with the symbol Ge and atomic number 32. It is lustrous, hard-brittle, grayish-white and similar in appearance to silicon. It is a metalloid in the carbon group that is chemically similar to its group neighbors s ...
atom. Germabenzene itself has been studied theoretically, and synthesized with a bulky 2,4,6-tris
is(trimethylsilyl)methyl
In linguistics, a copula (plural: copulas or copulae; abbreviated ) is a word or phrase that links the subject of a sentence to a subject complement, such as the word ''is'' in the sentence "The sky is blue" or the phrase ''was not being'' i ...
henyl or Tbt group. Also, stable
naphthalene
Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...
derivatives do exist in the laboratory such as the 2-germanaphthalene-containing substance represented below.
The germanium to carbon bond in this compound is shielded from potential reactants by a Tbt group. This compound is
aromatic
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
just as the other
carbon group
The carbon group is a periodic table group consisting of carbon (C), silicon (Si), germanium (Ge), tin (Sn), lead (Pb), and flerovium (Fl). It lies within the p-block.
In modern IUPAC notation, it is called group 14. In the field of semicond ...
representatives
silabenzene
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), trisilabenz ...
and
stannabenzene
Stannabenzene (C5H6Sn) is the parent representative of a group of organotin compounds that are related to benzene with a carbon atom replaced by a tin atom. Stannabenzene itself has been studied by computational chemistry, but has not been isolat ...
.
:
See also
* 6-membered aromatic rings with one carbon replaced by another group:
borabenzene
Borabenzene is a hypothetical organoboron compound with the formula C5H5B. Unlike the related but highly stable benzene molecule, borabenzene would be electron-deficient. Related derivatives are the boratabenzene anions, including the parent 5H5 ...
,
silabenzene
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), trisilabenz ...
, germabenzene,
stannabenzene
Stannabenzene (C5H6Sn) is the parent representative of a group of organotin compounds that are related to benzene with a carbon atom replaced by a tin atom. Stannabenzene itself has been studied by computational chemistry, but has not been isolat ...
,
pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...
,
phosphorine
Phosphorine (IUPAC name: phosphinine) is a heavier element analog of pyridine, containing a phosphorus atom instead of an aza- moiety. It is also called phosphabenzene and belongs to the phosphaalkene class. It is a colorless liquid that is m ...
,
arsabenzene
Arsabenzene (IUPAC name: arsinine) is an organoarsenic heterocyclic compound with the chemical formula C5H5As. It belongs to a group of compounds called heteroarenes that have the general formula C5H5E (E= N, P, As, Sb, Bi).
This air sensitive li ...
,
bismabenzene
Bismabenzene () is the parent representative of a group of organobismuth compounds that are related to benzene with a carbon atom replaced by a bismuth atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive, te ...
,
pyrylium
Pyrylium is a cation (positive ion) with formula , consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aroma ...
,
thiopyrylium
Thiopyrylium is a cation with the chemical formula C5H5S+. It is analogous to the pyrylium cation with the oxygen atom replaced by a sulfur atom.
Thiopyrylium salts are less reactive than the analogous pyrylium salts due to the higher polarizab ...
,
selenopyrylium
Selenopyrylium is an aromatic heterocyclic compound consisting of a six-membered ring with five carbon atoms and a positively charged selenium atom.
Naming and numbering
Formerly it was named selenapyrylium. However, this is misleading as "selena ...
,
telluropyrylium
Telluropyrylium is an aromatic heterocyclic compound consisting of a six member ring with five carbon atoms, and a positively charged tellurium atom. Derivatives of telluropyrylium are important in research of infrared dyes.
Naming and numbering ...
References
{{reflist
Germanium heterocycles
Germanium(IV) compounds
Six-membered rings
Hypothetical chemical compounds