Dithiete
| Names | |
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| Preferred IUPAC name
1,2-Dithiete | |
| Systematic IUPAC name
1,2-Dithiacyclobut-3-ene | |
| Other names
Dithiete
Dithiacyclobutene 1,2-Dithia[4]annulene | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C2H2S2 | |
| Molar mass | 90.16 g·mol−1 |
| Related compounds | |
Related thietes
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Thiete |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dithiete is an unsaturated heterocyclic compound that contains two adjacent sulfur atoms and two sp2-hybridized carbon centers. Derivatives are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of aromatic organosulfur compounds. A few 1,2-dithietes have been isolated;[1][2][3] one (low-yielding) route is oxidation of a dithiolene complex.[4] 3,4-Bis(trifluoromethyl)-1,2-dithiete is a particularly stable example.
Unsubstituted 1,2-dithiete has been generated in thermolytic reactions and was characterized by microwave spectroscopy, ultraviolet photoelectron spectroscopy and infrared spectroscopy in a low temperature matrix. The open ring isomer, dithioglyoxal, HC(S)C(S)H, is less stable than the 1,2-dithiete.[5]
The dithione can be prepared (as trans-dithioglyoxal) by low temperature photolysis of 1,3-dithiol-2-one.[6] Quantum chemical calculations reproduce the observed greater stability of 1,2-dithiete only if large basis-sets with polarization functions are used.[7]
File:HONKOK.png Structure of the dithiete S2C2(CO2Me)2. Selected distances and angles: rC=C = 1.362, rC-S = 1.738, rS-S = 2.072 Å, <S-S-C = 78.3°, <S-C-S = 102°.[4]
See also
[edit | edit source]- Dithietane - the corresponding saturated ring
- Thiete - an analogue with only one sulfur atom
Additional reading
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References
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