View source for 1,4,7-Trithiacyclononane

{{chembox
|   ImageFile = 9-ane-S3.svg
|   ImageSize =
|   IUPACName = 1,4,7-Trithionane
|   OtherNames = 1,4,7-Trithiacyclononane, Triethylene trisulfide, 9-ane-S3, [9]aneS<sub>3</sub>
| Section1 = {{Chembox Identifiers
|   CASNo = 6573-11-1
|   PubChem = 373835
|   SMILES = C1CSCCSCCS1
|   ChEBI = 37418
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>6</sub>H<sub>12</sub>S<sub>3</sub>
|   MolarMass = 180.35 g/mol
|   Appearance = Colourless solid
|   Density =
|   MeltingPt = 78 - 81 °C
|   BoilingPt = Decomp.
|   Solubility = Insoluble
|   SolubleOther = [[Chlorocarbon]]s, [[acetone]]
  }}
| Section7 = {{Chembox Hazards
|   MainHazards = Toxic ('''T''')
|   RPhrases = {{R36/37/38}}
|   SPhrases = {{S26}}, {{S36}}
|   FlashPt =
|   Autoignition =
  }}
| Section8 = {{Chembox Related
|   OtherAnions =
|   OtherCations =
|   OtherFunctn =
|   Function =
|   OtherCpds = [[Thiirane]], [[1,3,5-Trithiane]], [[Triazacylononane]]
  }}
}}

'''1,4,7-Trithiacyclononane''', also called 9-ane-S3, is the [[heterocyclic compound]] with the formula (CH<sub>2</sub>CH<sub>2</sub>S)<sub>3</sub>.  This cyclic [[thioether]] is most often encountered as a [[tridentate]] [[ligand]] in [[coordination chemistry]].

9-ane-S3 forms complexes with many metal ions, including those considered [[HSAB theory|hard]], such as copper(II) and iron(II).<ref>{{cite journal | author = Kueppers, H. J.; Wieghardt, K.; Nuber, B.; Weiss, J. W.; Bill, E. and Trautwein, A. X. | date = 1987 | title = Crown Thioether Chemistry of Iron(II/III). Synthesis and Characterization of Low-spin Bis(1,4,7-trithiacyclononane)iron(III) and crystal structure of [FeII([9]aneS3)([9]aneS3(O))](ClO4)2.2NaClO4<sup>.</sup>H2O | journal = Inorganic Chemistry | volume = 26 | issue = | pages = 3762–3769(8) | pmid = | doi = 10.1021/ic00269a028| url = | accessdate = }}</ref>  Most of its complexes have the formula [M(9-ane-S3)<sub>2</sub>]<sup>2+</sup> and are [[octahedral geometry|octahedral]].

It was first reported in 1977,<ref>{{cite journal | author = Gerber, D.; Chongsawangvirod, P.; Leung, A. K.; Ochrymowycz, L. A. | date = 1977 | title = Synthesis of the Torsionally Strained Monocyclic Polythiaether 1,4,7-Trithiacyclononane | journal = Journal of Organic Chemistry | volume = 42 | issue = | pages = 2644–2645(2) | pmid = | doi = | url = | accessdate = }}</ref> and the current synthesis entails the assembly within the [[coordination sphere]] of a metal ion followed by decomplexation.<ref>{{cite journal | author = Sellmann, D.; Zapf, L. | date = 1984 | title = Simple Route to 1,4,7-Trithiacyclononane | journal = Angewandte Chemie | volume = 96 | issue = | pages = 799–800(2) | pmid = | doi = 10.1002/ange.19840961019| url = | accessdate = }}</ref>

==References==
<references/>

{{DEFAULTSORT:Trithiacyclononane, 1,4,7-}}
[[Category:Chelating agents]]
[[Category:Sulfur heterocycles]]
[[Category:Thioethers]]
[[Category:Macrocycles]]
[[Category:2Fix]]