1,4,7-Trithiacyclononane
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| Names | |
|---|---|
| IUPAC name
1,4,7-Trithionane | |
| Other names
1,4,7-Trithiacyclononane, Triethylene trisulfide, 9-ane-S3, [9]aneS3 | |
| Identifiers | |
6573-11-1  | |
| 3D model (Jmol) | Interactive image Interactive image |
| ChEBI | CHEBI:37418  |
| ChemSpider | 331656 |
| ECHA InfoCard | 100.150.510 |
| PubChem | 373835 |
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| 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| 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
- ↑ 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.
- ↑ 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.
- ↑ 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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