View source for Thiepine

{{Distinguish|Thiepane}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470606489
| ImageFileL1 = Thiepine.png
| ImageFileL1_Ref = {{Chemboximage|correct|??}}
| ImageSizeL1 = 105
| ImageAltL1 = Structural formula of thiepine
| ImageFileR1 = Thiepine-3D-balls.png
| ImageSizeR1 = 135
| ImageAltR1 = Ball-and-stick model of the thiepine molecule
| PIN = Thiepine
| OtherNames = Thiatropilidene<br />Thiepin
|Section1={{Chembox Identifiers
| CASNo = 291-72-5
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5A9XLZ8CPE
| PubChem = 12444286
| ChemSpiderID = 13299847
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = S1C=CC=CC=C1
| StdInChI = 1S/C6H6S/c1-2-4-6-7-5-3-1/h1-6H
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BISQTCXKVNCDDA-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=6 | H=6 | S=1 
}}
}}
In organic chemistry, '''thiepine''' (or '''thiepin''') is an [[Saturated and unsaturated compounds|unsaturated]] seven-membered [[heterocyclic compound]], with six [[carbon]] atoms and one [[sulfur]] atom.  The parent compound, C<sub>6</sub>H<sub>6</sub>S is unstable and is predicted to be antiaromatic.  Bulky derivatives have been isolated and shown by [[X-ray crystallography]] to have nonplanar C<sub>6</sub>S ring.<ref>Schwan, A. L., "Thiepins" Science of Synthesis, 2004, volume 17, 705. {{doi|10.1055/sos-SD-017-01065}}</ref>

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<sup>4</sup>-C<sub>6</sub>H<sub>6</sub>S)Fe(CO)<sub>3</sub>, the ring is stable.<ref>{{cite journal|doi=10.1021/ja00013a051 |title=Thiepine-iron tricarbonyl: Stabilization of thermally labile parent thiepine by transition metal complexation |date=1991 |last1=Nishino |first1=Keitaro |last2=Takagi |first2=Masanobu |last3=Kawata |first3=Teruhisa |last4=Murata |first4=Ichiro |last5=Inanaga |first5=Junji |last6=Nakasuji |first6=Kazuhiro |journal=Journal of the American Chemical Society |volume=113 |issue=13 |pages=5059–5060 }}</ref>

'''Benzothiepines''' have one fused [[benzene]] group and ''dibenzothiepines'' such as [[dosulepin]] and [[zotepine]] have two fused benzene groups. [[Damotepine]] is another thiepin derivative.
[[Image:zotepine structure.png|thumb|left|120px|The chemical structure of the dibenzothiepine [[zotepine]].]]{{clear-left}}

==See also==
* [[Thiazepines]]
* [[2,3-Dihydrothiepine]]
* [[2,7-Dihydrothiepine]]

==References==
<references />

==External links==
* {{MeshName|Thiepins}}
* {{MeshName|Benzothiepins}}

[[Category:Thiepines]]
[[Category:Antiaromatic compounds]]