Thiirane
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| Names | |||
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| Systematic IUPAC name
Thiirane[1]
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| Other names | |||
| Identifiers | |||
420-12-2  |
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| 102379 | |||
| ChEBI | CHEBI:30977 |
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| ChemSpider | 9481 |
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| EC Number | 206-993-9 | ||
| 1278 | |||
| Jmol 3D model | Interactive image | ||
| KEGG | C19419  |
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| MeSH | ethylene+sulfide | ||
| PubChem | 9865 | ||
| RTECS number | KX3500000 | ||
| UN number | 1992 | ||
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| Properties | |||
| C2H4S | |||
| Molar mass | 60.11 g·mol−1 | ||
| Appearance | Pale, yellow liquid | ||
| Density | 1.01 g cm−3 | ||
| Melting point | −109 °C (−164 °F; 164 K) | ||
| Boiling point | 56 °C; 133 °F; 329 K | ||
| Vapor pressure | 28.6 kPa (at 20 °C) | ||
| Thermochemistry | |||
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Std enthalpy of
formation (ΔfH |
51-53 kJ mol−1 | ||
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Std enthalpy of
combustion (ΔcH |
-2.0126 MJ mol−1 | ||
| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related heterocycles
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Ethylene oxide Aziridine Borirane |
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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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 verify (what is ?) |
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| Infobox references | |||
Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S.[2] It is the smallest sulfur-containing heterocycle and the simplest episulfide. Like many organosulfur compounds, this species has a stench. Thiirane is also used to describe any derivative of the parent ethylene sulfide.
Preparation
It is prepared by the reaction of ethylene carbonate and KSCN.[3] For this purpose the KSCN is first melted under vacuum to remove water.
- KSCN + C2H4O2CO → KOCN + C2H4S + CO2
Reactions
Ethylenesulfide adds to amines to afford 2-mercaptoethylamines,[4] which are good chelating ligands.
- C2H4S + R2NH → R2NCH2CH2SH
Dithiiranes
Dithiiranes are three membered rings containing two sulfur atoms and one carbon. One example was prepared by oxidation of a 1,3-dithietane.[5]
References
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- ↑ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.
- ↑ Ahhiko Ishii, Masamatsu Hoshino, and Juzo Nakayama "Recent Advances in Chemistry of Dithiirane and Small Ring Compounds Containing Two Chalcogen Atoms" Pure & Appl. Chem., 1996, volume 68, pp. 869-874.doi:10.1002/chin.199650272
