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 chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
, with six
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 ...
atoms and one
sulfur
Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...
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 determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...
to have nonplanar C
6S ring.
Theoretical 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.
[Nishino, K.; Takagi, M.; Kawata, T.; Murata, I.; Inanaga, J.; Nakasuji, K., "Thiepine-iron tricarbonyl: stabilization of thermally labile parent thiepine by transition metal complexation", J. Am. Chem. Soc. 1991, volume 113, 5059-5060.]
Benzothiepines have one fused
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, ...
group and ''dibenzothiepines'' such as
dosulepin
Dosulepin, also known as dothiepin and sold under the brand name Prothiaden among others, is a tricyclic antidepressant (TCA) which is used in the treatment of depression. Dosulepin was once the most frequently prescribed antidepressant in the ...
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
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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 sing ...
*
2,3-Dihydrothiepine
2,3-Dihydrothiepine is a partially saturated analog of thiepine
In organic chemistry, thiepine (or thiepin) is an unsaturated seven-membered heterocyclic compound, with six carbon atoms and one sulfur atom. The parent compound, C6H6S is unstab ...
*
2,7-Dihydrothiepine
2,7-Dihydrothiepine is a partially saturated analog of thiepine
In organic chemistry, thiepine (or thiepin) is an unsaturated seven-membered heterocyclic compound, with six carbon atoms and one sulfur atom. The parent compound, C6H6S is unstab ...
References
External links
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Thiepines
Antiaromatic compounds
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