Chemistry:1,4,7-Trithiacyclononane

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1,4,7-Trithiacyclononane
1,4,7-Trithiacyclononane.svg
1,4,7-Trithiacyclononane molecule
Names
Preferred IUPAC name
1,4,7-Trithionane
Other names
1,4,7-Trithiacyclononane, Triethylene trisulfide, 9-ane-S3, [9]aneS3
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 621-680-0
UNII
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
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Related compounds
Related compounds
 Thiirane, 1,3,5-Trithiane, 1,4,7-Triazacyclononane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,4,7-Trithiacyclononane, also called 9-ane-S3, is the thia-crown ether with the formula (CH2CH2S)3. This cyclic thioether is most often encountered as a tridentate ligand in coordination chemistry, where it forms transition metal thioether complexes.

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]

Synthesis of 9S3.png

References

  1. ↑ Kueppers, H. J.; Wieghardt, K.; Nuber, B.; Weiss, J. W.; Bill, E.; 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 (15): 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. 



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