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1,4,7-Trithiacyclononane

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). 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, and the current synthesis entails the assembly within the coordination sphere of a metal ion followed by decomplexation:

:[[File:Synthesis_of_9S3.png|500px]]

References

(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 Fe^II([9]aneS₃)([9]aneS₃(O))₂·2NaClO₄·H₂O". Inorganic Chemistry.
(1977). "Synthesis of the Torsionally Strained Monocyclic Polythiaether 1,4,7-Trithiacyclononane". Journal of Organic Chemistry.
(1984). "Simple Route to 1,4,7-Trithiacyclononane". Angewandte Chemie.

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chelating-agents sulfur-heterocycles thioethers macrocycles

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