1,4,7-Trithiacyclononane

1,4,7-Trithiacyclononane
1,4,7-Trithiacyclononane molecule
Names
IUPAC name
1,4,7-Trithionane
Other names
1,4,7-Trithiacyclononane, Triethylene trisulfide, 9-ane-S3, [9]aneS3
Identifiers
6573-11-1 
ChEBI CHEBI:37418 Yes
ChemSpider 331656 Yes
Jmol-3D images Image
Image
PubChem 373835
Properties
C6H12S3
Molar mass 180.35 g/mol
Appearance Colourless solid
Melting point 78 to 81 °C (172 to 178 °F; 351 to 354 K)
Boiling point decomposes
Insoluble
Solubility Chlorocarbons, acetone
Hazards
Main hazards Toxic (T)
R-phrases R36/37/38
S-phrases S26, S36
Related compounds
Related compounds
 Thiirane, 1,3,5-Trithiane, Triazacylononane
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

1,4,7-Trithiacyclononane, also called 9-ane-S3, is the heterocyclic compound with the formula (CH2CH2S)3. 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 hard, such as copper(II) and iron(II).[1] Most of its complexes have the formula [M(9-ane-S3)2]2+ and are octahedral. The point group of [M(9-ane-S3)2]2+ is S6.

Synthesis

This compound was first reported in 1977,[2] and the current synthesis entails the assembly within the coordination sphere of a metal ion followed by decomplexation:[3]

References

  1. ↑ Kueppers, H. J.; Wieghardt, K.; Nuber, B.; Weiss, J. W.; Bill, E. and Trautwein, A. X. (1987). "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.H2O". Inorganic Chemistry 26 (22): 3762–3769(8). doi:10.1021/ic00269a028.
  2. ↑ Gerber, D.; Chongsawangvirod, P.; Leung, A. K.; Ochrymowycz, L. A. (1977). "Synthesis of the Torsionally Strained Monocyclic Polythiaether 1,4,7-Trithiacyclononane". Journal of Organic Chemistry 42: 2644–2645. doi:10.1021/jo00435a030.
  3. ↑ Sellmann, D.; Zapf, L. (1984). "Simple Route to 1,4,7-Trithiacyclononane". Angewandte Chemie 96 (10): 799–800(2). doi:10.1002/ange.19840961019.