1,4,7-Trithiacyclononane

1,4,7-Trithiacyclononane
Names
	IUPAC name 1,4,7-Trithionane
	Other names 1,4,7-Trithiacyclononane, Triethylene trisulfide, 9-ane-S3, [9]aneS3
Identifiers
CAS Number	6573-11-1 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:37418 ;
ChemSpider	331656 ;
ECHA InfoCard	100.150.510
PubChem CID	373835;
CompTox Dashboard (EPA)	DTXSID40215934 ;
	InChI InChI=1S/C6H12S3/c1-2-8-5-6-9-4-3-7-1/h1-6H2 Key: PQNPKQVPJAHPSB-UHFFFAOYSA-N ; InChI=1/C6H12S3/c1-2-8-5-6-9-4-3-7-1/h1-6H2 Key: PQNPKQVPJAHPSB-UHFFFAOYAS;
	SMILES C1CSCCSCCS1; S1CCSCCSCC1;
Properties
Chemical formula	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
Solubility in water	Insoluble
Solubility	Chlorocarbons, acetone
Hazards
Main hazards	Toxic (T)
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26, S36
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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	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]

Related ligands

1,4,7-Trithiacyclononane is one of several thia crown ethers, analogues of crown ethers with S in place of O. They exhibit affinities for transition metals. Another thia crown ligan are the tetradentate 14-ane-S4[4] and the hexadentate 18-ane-S6.[5]

Structure of the silver complex of a thiacrown ether [Ag(18-ane-S6)]²⁺.

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 (15): 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.
Prett, V; Diaddario, L; Dockal, E; Corfield, P; Ceccarelli, C; Glick, M; Ochrymowycz, L. A.; Rorabacher, D. B. (1983). "Ring size effects on the structure of macrocyclic ligand complexes: copper(II) complexes with 12-16-membered cyclic tetrathia ethers". Inorganic Chemistry. 22 (24): 3661–3670. doi:10.1021/ic00166a033.
Shaw, J; Wolowska, J; Collison, D; Howard, J; McInnes, E; McMaster, J; Blake, A; Wilson, C; Schroeder, M (2006). "Redox Non-innocence of Thioether Macrocycles: Elucidation of the Electronic Structures of Mononuclear Complexes of Gold(II) and Silver(II)". Journal of the American Chemical Society. 128 (42): 13827–13839. doi:10.1021/ja0636439.

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[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.

[4] Prett, V; Diaddario, L; Dockal, E; Corfield, P; Ceccarelli, C; Glick, M; Ochrymowycz, L. A.; Rorabacher, D. B. (1983). "Ring size effects on the structure of macrocyclic ligand complexes: copper(II) complexes with 12-16-membered cyclic tetrathia ethers". Inorganic Chemistry. 22 (24): 3661–3670. doi:10.1021/ic00166a033.

[5] Shaw, J; Wolowska, J; Collison, D; Howard, J; McInnes, E; McMaster, J; Blake, A; Wilson, C; Schroeder, M (2006). "Redox Non-innocence of Thioether Macrocycles: Elucidation of the Electronic Structures of Mononuclear Complexes of Gold(II) and Silver(II)". Journal of the American Chemical Society. 128 (42): 13827–13839. doi:10.1021/ja0636439.