Thiirane
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| Names | |||
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| Preferred IUPAC name
Thiirane | |||
| Systematic IUPAC name
Thiacyclopropane | |||
| Other names | |||
| Identifiers | |||
3D model (JSmol)
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| 102379 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). | ||
| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). | ||
| 1278 | |||
| KEGG | |||
| MeSH | ethylene+sulfide | ||
PubChem CID
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| RTECS number |
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| UNII | |||
| UN number | 1992 | ||
CompTox Dashboard (EPA)
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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 | |||
Std enthalpy of
formation (ΔfH⦵298) |
51–53 kJ mol−1 | ||
Std enthalpy of
combustion (ΔcH⦵298) |
−2.0126 MJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
| GHS02: Flammable GHS05: Corrosive GHS06: Toxic | |||
| Danger | |||
| H225, H301, H318, H331 | |||
| P210, P261, P280, P301+P310, P305+P351+P338, P311 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 10 °C (50 °F; 283 K) | ||
| Related compounds | |||
Related heterocycles
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Ethylene oxide Aziridine Borirane | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 highly unpleasant odour. Thiirane is also used to describe any derivative of the parent ethylene sulfide.
Structure and properties
[edit | edit source]According to electron diffraction, the C-C and C-S distances in ethylene sulfide are respectively 1.473 and 1.811 Å. The C-C-S and C-S-C angles are respectively 66.0 and 48.0°.[3] The microwave and infrared spectra were studied experimentally and computationally.[4]
Preparation and reactions
[edit | edit source]It can be prepared by the reaction of ethylene carbonate and KSCN.[5] For this purpose the KSCN is first melted under vacuum to remove water.
- KSCN + C2H4O2CO → KOCN + C2H4S + CO2
Ethylenesulfide adds to amines to afford 2-mercaptoethylamines,[6] which are good chelating ligands.
- C2H4S + R2NH → R2NCH2CH2SH
This process is often called mercaptoethylation.[7]
Oxidation of thiirane with periodate gives ethylene episulfoxide.
References
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- ^ R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
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