Cyclohexanehexathione

Cyclohexanehexathione
Names
	IUPAC name Cyclohexane-1,2,3,4,5,6-hexathione
	Other names 1,2,3,4,5,6-Cyclohexanehexathione; Cyclohexanehexathione;
Identifiers
CAS Number	129917-29-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	28680776 ;
PubChem CID	71340739;
CompTox Dashboard (EPA)	DTXSID00767863 ;
	InChI InChI=1S/C6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9 [pubchem] Key: PKRGYJHUXHCUCN-UHFFFAOYSA-N [pubchem]; InChI=1S/C6S6/c7-1-2(8)4(10)6(12)5(11)3(1)9 Key: OZKIZIQFPZROOY-UHFFFAOYSA-N;
	SMILES C1(=S)C(=S)C(=S)C(=S)C(=S)C1=S;
Properties
Chemical formula	C6S6
Molar mass	264.43 g·mol−1
	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

Cyclohexanehexathione is a cyclic covalent compound consisting of a six-carbon ring with a sulfur bonded to each. It has been synthesized by neutralization of its monoanion (C₆S₆^–) in a mass spectrometer.[1] This compound is the thioketone analog of cyclohexanehexone; that oxygen variant is expected to be substantially less stable.[2] Synthesis of C₆S₆ by photolysis or pyrolysis to extrude three equivalents of carbon monoxide from a precursor containing adjacent pairs of sulfurs as cyclic dithiocarbonate units gave what is more likely a different valence isomer, as various dithiete-containing structures are predicted to be more stable than the hexathione form.[3]

Proposed valence isomers of cyclohexanehexathione

This theoretical analysis of the various isomers and experimental analysis of this reaction cast doubt on whether the mass spectrometric approach really did produce the hexathione isomer as originally claimed. The increased stability of dithietes as compared to dioxetane-like rings is one of theoretical bases for proposing C₆S₆ is more stable than the oxygen analog.[2]

References

Sülzle, Detlev; Beye, Norbert; Fanghänel, Egon; Schwarz, Helmut (1989). "Generation of C₆S₆ and its radical anion and cation in the gas phase". Chem. Ber. 122: 2411–2412. doi:10.1002/cber.19891221233.
Schröder, Detlef; Schwarz, Helmut; Dua, Suresh; Blanksby, Stephen J.; Bowie, John H. (1999). "Mass spectrometric studies of the oxocarbons C_nO_n (n = 3–6)". International Journal of Mass Spectrometry. 188 (1–2): 17–25. doi:10.1016/S1387-3806(98)14208-2. ISSN 1387-3806.
Nakayama, Juzo; Ishii, Akihiko (2000). "Chapter 5: Chemistry of Dithiiranes, 1,2-Dithietanes, and 1,2-Dithietes". Advances in Heterocyclic Chemistry. 77. Academic Press. pp. 221–284. ISBN 9780080549637.

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[1] Sülzle, Detlev; Beye, Norbert; Fanghänel, Egon; Schwarz, Helmut (1989). "Generation of C₆S₆ and its radical anion and cation in the gas phase". Chem. Ber. 122: 2411–2412. doi:10.1002/cber.19891221233.

[Schröder-2] Schröder, Detlef; Schwarz, Helmut; Dua, Suresh; Blanksby, Stephen J.; Bowie, John H. (1999). "Mass spectrometric studies of the oxocarbons C_nO_n (n = 3–6)". International Journal of Mass Spectrometry. 188 (1–2): 17–25. doi:10.1016/S1387-3806(98)14208-2. ISSN 1387-3806.

[3] Nakayama, Juzo; Ishii, Akihiko (2000). "Chapter 5: Chemistry of Dithiiranes, 1,2-Dithietanes, and 1,2-Dithietes". Advances in Heterocyclic Chemistry. 77. Academic Press. pp. 221–284. ISBN 9780080549637.