二硫雜環丁烯
| 二硫雜環丁烯 | |
|---|---|
| |
| IUPAC名 1,2-Dithiete | |
| 系統名 1,2-Dithiacyclobut-3-ene | |
| 別名 | 二噻環丁烯 1,2-二噻[4]輪烯 |
| 識別 | |
| CAS號 | 7092-01-5 |
| PubChem | 138918 |
| ChemSpider | 122516 |
| SMILES |
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| 性質 | |
| 化學式 | C2H2S2 |
| 摩爾質量 | 90.17 g·mol−1 |
| 相關物質 | |
| 相關化合物 | 硫雜環丁烯 |
| 相關化學品 | |
| 若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。 | |
二硫雜環丁烯（英語：Dithiete）是一種不飽和雜環化合物，含有兩個相鄰的硫原子和兩個sp2雜化碳中心。衍生物統稱為二硫雜環丁烯化合物或1,2-二硫雜環丁烯化合物。具有6個π電子的1,2-二硫醚是芳香族有機硫化合物的例子。一些1,2-二硫雜環丁烯化合物已被分離出來。[1][2]3,4-雙(三氟甲基)-1,2-二硫雜環丁烯是一個特別穩定的例子。
未取代的1,2-二硫雜環丁烯在熱解反應中生成，並在低溫基質中通過微波光譜、紫外光電子能譜和紅外光譜進行了表徵。開環異構體二硫乙二醛的穩定性低於1,2-二硫雜環丁烯。[3]
二硫酮可以通過1,3-二硫醇-2-酮的低溫光解來製備（作為反式二硫乙二醛）。[4]僅當使用具有極化函數的大基組時，量子化學計算才能重現所觀察到的 1,2-二硫醚的更高穩定性。[5]
二硫雜環丁烯S2C2(CO2Me)2的結構。選定的距離和角度：rC=C = 1.362、rC-S = 1.738、rS-S = 2.072 Å、<S-S-C = 78.3°、<S-C-S = 102°.[6]
參見
[編輯]延伸閱讀
[編輯]- Diehl, F.; Meyer, H.; Schweig, A.; Hess, B. A.; Fabian, J. 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. September 1989, 111 (19): 7651–7653. doi:10.1021/ja00201a076.
- Vijay, D; Priyakumar, UD; Sastry, GN. Basis set and method dependence of the relative energies of C2S2H2 isomers. Chemical Physics Letters. 2004, 383 (1–2): 192–197. Bibcode:2004CPL...383..192V. doi:10.1016/j.cplett.2003.11.021.
- Jonas, V; Frenking, G. 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. 1991, 177 (2): 175–183. Bibcode:1991CPL...177..175J. doi:10.1016/0009-2614(91)90064-G.
- Gonzalez, L; Mo, O; Yanez, M. High-level ab initio calculations on the 1,2-dithioglyoxal/1,2-dithiete isomerism. Chemical Physics Letters. 13 December 1996, 263 (3): 407–413(7). Bibcode:1996CPL...263..407G. doi:10.1016/S0009-2614(96)01240-7.
參考資料
[編輯]- ^ Drabowicz, J; Lewkowski, J; Kudelska, W; Zając, A. Four-membered Rings with Two Sulfur Atoms. Comprehensive Heterocyclic Chemistry III 2. 2008: 811–852. ISBN 978-0-08-044992-0. doi:10.1016/B978-008044992-0.00218-2.
- ^ Zoller, U. Four-membered Rings with Two Sulfur Atoms. Comprehensive Heterocyclic Chemistry II 1B. 1996: 1113–1138. ISBN 978-0-08-096518-5. doi:10.1016/B978-008096518-5.00035-6.
- ^ Reinhard Schulz; Armin Schweig; Klaus Hartke; Joachim Koester. Theory and application of photoelectron spectroscopy. 100. Variable-temperature photoelectron spectral study of 1,3-dithiol-2-one and 4,5-disubstituted 1,3-dithiol-2-ones. Thermal generation of 1,2-dithiete, 3,4-disubstituted 1,2-dithietes, and dialkyl tetrathiooxalates. Journal of the American Chemical Society. 1983, 105 (14): 4519–4528. doi:10.1021/ja00352a004.
- ^ Mucha, M; Pagacza, M; Mielke, Z. Infrared detection of dithioglyoxal from photolysis of 1,3-dithiol-2-one in solid argon and nitrogen. Chemical Physics Letters. 6 June 2008, 458 (1–3): 39–43. Bibcode:2008CPL...458...39M. doi:10.1016/j.cplett.2008.04.088.
- ^ Frolov, YV; Vashchenko, AV; Mal'kina, AG; Trofimov, BA. Ab initio quantum-chemical calculations of the energies and structures of 1,2-acetylenedithiol isomers. Journal of Structural Chemistry. 2009, 50 (2): 195–200. S2CID 93780466. doi:10.1007/s10947-009-0029-8.
- ^ T. Shimizu; H. Murakami; Y. Kobayashi; K. Iwata; N. Kamigata. Synthesis, Structure, and Ring Conversion of 1,2-Dithiete and Related Compounds. J. Org. Chem. 1998, 63 (23): 8192–8199. doi:10.1021/jo9806714.