1,4,7-trithiacyclononane

1,4,7-Trithiacyclononane

1,4,7-Trithiacyclononane

Chemical compound

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.

Quick Facts Names, Identifiers ...

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. [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. [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. [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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