thiirane
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470606690
| ImageFile2 = Ethylene-sulfide-3D-balls.png
| ImageFile2_Ref = {{chemboximage|correct|??}}
| ImageSize2 = 121
| ImageName2 = Ball-and-stick model of thiirane
| ImageFileL1 = Ethylene-sulfide-2D-skeletal.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageSizeL1 = 121
| ImageNameL1 = Skeletal formula of thiirane
| ImageFileR1 = Ethylene-sulfide-3D-vdW.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageSizeR1 = 121
| ImageNameR1 = Spacefill model of thiirane
| PIN = Thiirane
| SystematicName = Thiacyclopropane
| OtherNames = 2,3-Dihydrothiirene{{Cite web|url = http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30977|title = thiirane (CHEBI:30977)|work = Chemical Entities of Biological Interest (ChEBI)|location = UK|publisher = European Bioinformatics Institute}}
Ethylene sulfide
|Section1={{Chembox Identifiers
| CASNo = 420-12-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = A2W5165740
| PubChem = 9865
| ChemSpiderID = 9481
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 206-993-9
| UNNumber = 1992
| KEGG = C19419
| KEGG_Ref = {{keggcite|changed|kegg}}
| MeSHName = ethylene+sulfide
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30977
| RTECS = KX3500000
| Beilstein = 102379
| Gmelin = 1278
| SMILES = C1CS1
| StdInChI = 1S/C2H4S/c1-2-3-1/h1-2H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VOVUARRWDCVURC-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=2 | H=4 | S=1
| Appearance = Pale, yellow liquid
| Density = 1.01 g cm−3
| MeltingPtC = -109
| BoilingPtK = 329
| VaporPressure = 28.6 kPa (at 20 °C)
}}
|Section4={{Chembox Thermochemistry
| DeltaHf = 51–53 kJ mol−1
| DeltaHc = −2.0126 MJ mol−1
}}
|Section5={{Chembox Hazards
| GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS skull and crossbones}}
| GHSSignalWord = DANGER
| HPhrases = {{H-phrases|225|301|318|331}}
| PPhrases = {{P-phrases|210|261|280|301+310|305+351+338|311}}
| NFPA-F = 4
| NFPA-H = 3
| NFPA-R = 2
| FlashPtC = 10
}}
|Section6={{Chembox Related
| OtherFunction_label = heterocycles
| OtherFunction = Ethylene oxide
Aziridine
Borirane
}}
}}
{{for|the class of compounds known as thiiranes|Episulfide}}
Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S.{{cite journal
| author= Warren Chew |author2=David N. Harpp
| title = Recent aspects of thiirane chemistry
| journal = Journal of Sulfur Chemistry
| year = 1993
| volume = 15
| issue = 1
| pages = 1–39
| doi = 10.1080/01961779308050628}} 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
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°.{{cite encyclopedia|encyclopedia=Comprehensive Heterocyclic Chemistry II|volume=1A|year=1996|pages=173–240|title=Thiiranes and Thiirenes: Monocyclic |author=Wataru Ando |author2=Nami Choi |author3=Norihiro Tokitoh |doi=10.1016/B978-008096518-5.00005-8|isbn=978-0-08-096518-5}} The microwave and infrared spectra were studied experimentally and computationally.{{Cite journal |last1=De Vos |first1=John |last2=Schröder |first2=Benjamin |last3=Rauhut |first3=Guntram |date=2023-12-05 |title=Comprehensive quantum chemical analysis of the (ro)vibrational spectrum of thiirane and its deuterated isotopologue |url=https://linkinghub.elsevier.com/retrieve/pii/S1386142523007680 |journal=Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy |volume=302 |pages=123083 |doi=10.1016/j.saa.2023.123083 |pmid=37423098 |bibcode=2023AcSpA.30223083D |issn=1386-1425|hdl=1854/LU-01HP1F40851T3MX6QGN9QBHR4E |hdl-access=free }}
Preparation and reactions
It can be prepared by the reaction of ethylene carbonate and KSCN.{{cite journal| author1 = Searles, S. | author2 = Lutz, E. F. | author3 = Hays, H. R. | author4 = Mortensen, H. E. | title = Ethylene Sulfide | year = 1962| volume = 42 | page = 59 | doi= 10.15227/orgsyn.042.0059|journal=Organic Syntheses|doi-access=free}} 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,R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). {{ISBN|0-471-95512-4}}. which are good chelating ligands.
:C2H4S + R2NH → R2NCH2CH2SH
This process is often called mercaptoethylation.{{cite encyclopedia|title=Ethylene Sulfide|author=Gunars Zelans |author2=Jacquelyn Gervay-Hague |author3=Ivy Maulie |encyclopedia= Encyclopedia of Reagents for Organic Synthesis|year=2010|publisher= John Wiley & Sons|doi=10.1002/047084289X.re079.pub2|isbn=978-0-471-93623-7}}
Oxidation of thiirane with periodate gives ethylene episulfoxide.