| Revision as of 12:58, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 452163525 of page Thiepine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 18:13, 14 April 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,550 edits ref repair |
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{{Distinguish|Thiepane}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 439653460 |
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| Watchedfields = changed |
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| ImageFile = Thiepine.png |
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| verifiedrevid = 470606489 |
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| ImageFile_Ref = {{Chemboximage|correct|??}} |
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| ImageFileL1 = Thiepine.png |
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| ImageSize = 121 |
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| ImageFileL1_Ref = {{Chemboximage|correct|??}} |
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| ImageName = Structural formula of thiepine |
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| IUPACName = Thiepine |
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| ImageSizeL1 = 105 |
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| ImageAltL1 = Structural formula of thiepine |
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| SystematicName = <!-- Thienpine --> |
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| ImageFileR1 = Thiepine-3D-balls.png |
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| OtherNames = Thiatropilidene<br /> |
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| ImageSizeR1 = 135 |
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Thiepin |
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| ImageAltR1 = Ball-and-stick model of the thiepine molecule |
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| Section1 = {{Chembox Identifiers |
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| PIN = Thiepine |
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| CASNo = <!-- blanked - oldvalue: 291-72-5 --> |
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| OtherNames = Thiatropilidene<br />Thiepin |
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| CASNo_Ref = {{cascite|??|??}} |
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|Section1={{Chembox Identifiers |
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| PubChem = 12444286 |
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| CASNo = 291-72-5 |
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| PubChem_Ref = {{Pubchemcite|correct|PubChem}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChemSpiderID = 13299847 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = S1C=CC=CC=C1 |
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| UNII = 5A9XLZ8CPE |
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| PubChem = 12444286 |
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| StdInChI = 1S/C6H6S/c1-2-4-6-7-5-3-1/h1-6H |
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| ChemSpiderID = 13299847 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = BISQTCXKVNCDDA-UHFFFAOYSA-N |
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| SMILES = S1C=CC=CC=C1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H6S/c1-2-4-6-7-5-3-1/h1-6H |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BISQTCXKVNCDDA-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 6 |
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| C=6 | H=6 | S=1 |
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| H = 6 |
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| S = 1 |
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| ExactMass = 110.019020882 g mol<sup>-1</sup>}} |
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In organic chemistry, '''thiepine''' (or '''thiepin''') is an ] seven-membered ], with six ] atoms and one ] 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 ] 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> |
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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> |
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'''Benzothiepines''' have one fused ] group and ''dibenzothiepines'' such as ] and ] have two fused benzene groups. ] is another thiepin derivative. |
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].]]{{clear-left}} |
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==See also== |
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* ] |
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* ] |
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* ] |
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==References== |
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<references /> |
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==External links== |
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* {{MeshName|Thiepins}} |
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* {{MeshName|Benzothiepins}} |
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] |
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] |
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{{heterocyclic-stub}} |