Dithiete
| |
| Names | |
|---|---|
| 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 ) |
|
| ChemSpider | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C2H2S2 | |
| Molar mass | 90.16 g·mol−1 |
| Related compounds | |
Related thietes
|
Thiete |
Related compounds
|
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Dithiete is an unsaturated
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
polarization functions are used.[7]
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
- Dithietane - the corresponding saturated ring
- Thiete - an analogue with only one sulfur atom
Additional reading
- Diehl, F.; Meyer, H.; Schweig, A.; Hess, B. A.; Fabian, J. (September 1989). "1,2-Dithiete is more stable than 1,2-dithioglyoxal as evidenced by a combined experimental and theoretical IR spectroscopic approach". J. Am. Chem. Soc. 111 (19): 7651–7653. .
- Vijay, D; Priyakumar, UD; Sastry, GN (2004). "Basis set and method dependence of the relative energies of C2S2H2 isomers". Chemical Physics Letters. 383 (1–2): 192–197. .
- Jonas, V; Frenking, G (1991). "On the crucial importance of polarization functions for the calculation of molecules with third-row elements: the conformations of chlorocarbonyl isocyanate ClC(O)NCO and the equilibrium of 1,2-dithioglyoxal with its cyclic isomer 1,2-dithiete". Chemical Physics Letters. 177 (2): 175–183. .
- Gonzalez, L; Mo, O; Yanez, M (13 December 1996). "High-level ab initio calculations on the 1,2-dithioglyoxal/1,2-dithiete isomerism". Chemical Physics Letters. 263 (3): 407–413(7). .
References
- ISBN 978-0-08-096518-5.
- ISBN 978-0-08-044992-0.
- PMID 9760719.
- ^ .
- .
- .
- S2CID 93780466.