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词条 Dithiete
释义

  1. See also

  2. Additional reading

  3. References

{{Chembox
| ImageFile = Dithiete.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 100
| ImageName = Kekulé, skeletal formula of dithiete with all explicit hydrogens added
|Section1={{Chembox Identifiers
| CASNo = 7092-01-5
| PubChem = 138918
| ChemSpiderID = 122516
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = c1css1
| SMILES1 = S1SC=C1
| StdInChI = 1S/C2H2S2/c1-2-4-3-1/h1-2H
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CTGHONDBXRRMRC-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=2 | H=2 | S=2
}}
|Section3={{Chembox Related
| OtherFunction_label = thietes
| OtherFunction = Thiete
| OtherCompounds = {{Unbulleted list|Thiirene|2,3-Dihydrothiophene|Thiophene}}
}}
}}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]

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.[4]

The dithione can be prepared (as trans-dithioglyoxal) by low temperature photolysis of 1,3-dithiol-2-one.[5] Quantum chemical calculations reproduce the observed greater stability of 1,2-dithiete only if large basis-sets with polarization functions are used.[6]

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See also

  • Dithietane - the corresponding saturated ring
  • Thiete - an analogue with only one sulfur atom

Additional reading

  • {{cite journal | last1 = Diehl | first1 = F. | first2 = H. | last2 = Meyer | first3 = A. | last3 = Schweig | first4 = B. A. | last4 = Hess | first5 = J. | last5 = Fabian | date=September 1989 | title = 1,2-Dithiete is more stable than 1,2-dithioglyoxal as evidenced by a combined experimental and theoretical IR spectroscopic approach | journal = J. Am. Chem. Soc. | volume = 111 | issue = 19 | pages = 7651–7653 | doi = 10.1021/ja00201a076 }}
  • {{cite journal | author1 =Vijay, D| author2 =Priyakumar, UD| author3 =Sastry, GN| title = Basis set and method dependence of the relative energies of C2S2H2 isomers| journal =Chemical Physics Letters | year = 2004| volume = 383| issue = 1–2 | pages = 192–197 | doi= 10.1016/j.cplett.2003.11.021|bibcode = 2004CPL...383..192V }}
  • {{cite journal | author1 = Jonas, V | author2 = Frenking, G | title = 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 | journal = Chemical Physics Letters | year = 1991 | volume = 177 | issue = 2 | pages = 175–183 | doi = 10.1016/0009-2614(91)90064-G |bibcode = 1991CPL...177..175J }}
  • {{cite journal | author1 = Gonzalez, L | author2 = Mo, O | author3 = Yanez, M | title = High-level ab initio calculations on the 1,2-dithioglyoxal/1,2-dithiete isomerism | journal = Chemical Physics Letters | volume = 263 | issue = 3 | date = 13 December 1996 | pages = 407–413(7) | doi = 10.1016/S0009-2614(96)01240-7 | bibcode=1996CPL...263..407G}}

References

1. ^{{cite book |last=Drabowicz |first=J |author2=Lewkowski, J |author3=Kudelska, W |author4= Zając, A | title =Four-membered Rings with Two Sulfur Atoms |journal =Comprehensive Heterocyclic Chemistry III |year=2008 |volume=2.18 |pages=811–852 |doi=10.1016/B978-008044992-0.00218-2|isbn=9780080449920 }}
2. ^{{cite book |last=Zoller |first=U | title =Four-membered Rings with Two Sulfur Atoms |journal =Comprehensive Heterocyclic Chemistry II |year=1996 |volume=1.35 |pages=1113–1138 |doi=10.1016/B978-008096518-5.00035-6|isbn=9780080965185 }}
3. ^{{cite journal | author1 = Donahue, JP | author2 = Holm, RH | title = 3,4-Bis(1-adamantyl)-1,2-dithiete: the First Structurally Characterized Dithiete Unsupported by a Ring or Benzenoid Frame | journal = Acta Crystallographica | year = 1998 | volume = C54 | pages = 1175–1178 | doi = 10.1107/S0108270198002935 | issue = 8 }}
4. ^{{Cite journal| author1 = Reinhard Schulz| author2 = Armin Schweig| author3 = Klaus Hartke| author4 = Joachim Koester| title = 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 = Journal of the American Chemical Society| volume = 105| issue = 14| pages = 4519–4528| year = 1983 | doi = 10.1021/ja00352a004}}
5. ^{{cite journal | author1 = Mucha, M | author2 = Pagacza, M | author3 = Mielke, Z | title = Infrared detection of dithioglyoxal from photolysis of 1,3-dithiol-2-one in solid argon and nitrogen | journal = Chemical Physics Letters | volume = 458 | issue = 1–3 | date = 6 June 2008 | pages = 39–43 | doi = 10.1016/j.cplett.2008.04.088 |bibcode = 2008CPL...458...39M }}
6. ^{{cite journal | author1 =Frolov, YV | author2 = Vashchenko, AV | author3 = Mal’kina, AG| author4 = Trofimov, BA| title = Ab initio quantum-chemical calculations of the energies and structures of 1,2-acetylenedithiol isomers | journal =Journal of Structural Chemistry | year = 2009| volume = 50| issue = 2 | pages = 195–200 | doi = 10.1007/s10947-009-0029-8}}
7. ^{{cite journal|title=Synthesis, Structure, and Ring Conversion of 1,2-Dithiete and Related Compounds|journal=J. Org. Chem.|year=1998|volume=63|pages=8192-8199|authors= T. Shimizu, H. Murakami, Y. Kobayashi, K. Iwata, N. Kamigata|doi=10.1021/jo9806714}}

4 : Organosulfur compounds|Organic disulfides|Sulfur heterocycles|Four-membered rings
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