In organic chemistry, thiepine (or thiepin) is an
unsaturated seven-membered
heterocyclic compound
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...
, with six
carbon
Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
atoms and one
sulfur
Sulfur ( American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms ...
atom. The parent compound, C
6H
6S is unstable and is predicted to be antiaromatic. Bulky derivatives have been isolated and shown by
X-ray crystallography
X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...
to have nonplanar C
6S ring.
Computational studies suggest that thiepine would eliminate a sulfur atom to form benzene. The intermediate is this process is the bicycle thianorcaradiene. In the complex with (η
4-C
6H
6S)Fe(CO)
3, the ring is stable.
Benzothiepines have one fused
benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
group and ''dibenzothiepines'' such as
dosulepin and
zotepine
Zotepine is an atypical antipsychotic drug indicated for acute and chronic schizophrenia. It has been used in Germany since 1990 (although it has been discontinued in Germany) and Japan since 1982.
Zotepine is not approved for use in the United ...
have two fused benzene groups.
Damotepine is another thiepin derivative.
See also
*
Thiazepines
Thiazepines are substituted thiepins, with a nitrogen replacing a carbon in the seven-membered heterocyclic compound. Depending on the location of the nitrogen, one distinguishes 1,3-thiazepine and 1,4-thiazepine.
Benzothiazepines have a single ...
*
2,3-Dihydrothiepine
*
2,7-Dihydrothiepine
References
External links
*
* {{MeshName, Benzothiepins
Thiepines
Antiaromatic compounds