Thiirane

Thiirane

Skeletal formula of thiirane Spacefill model of thiirane
Ball-and-stick model of thiirane
Names
Preferred IUPAC name Thiirane
Systematic IUPAC name Thiacyclopropane
Other names 2,3-Dihydrothiirene [1] Ethylene sulfide [1]
Identifiers
CAS Number	420-12-2  Y
3D model (JSmol)	Interactive image
Beilstein Reference	102379
ChEBI	CHEBI:30977  Y
ChemSpider	9481  Y
ECHA InfoCard	100.006.359
EC Number	206-993-9
Gmelin Reference	1278
KEGG	C19419  N
MeSH	ethylene+sulfide
PubChem CID	9865
RTECS number	KX3500000
UNII	A2W5165740  Y
UN number	1992
CompTox Dashboard (EPA)	DTXSID3049411
InChI InChI=1S/C2H4S/c1-2-3-1/h1-2H2 Y Key: VOVUARRWDCVURC-UHFFFAOYSA-N Y
SMILES C1CS1
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H318, H331
Precautionary statements	P210, P261, P280, P301+P310, P305+P351+P338, P311
NFPA 704 (fire diamond)	3 4 2
Flash point	10 °C (50 °F; 283 K)
Related compounds
Related heterocycles	Ethylene oxide Aziridine Borirane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

For the class of compounds known as thiiranes, see Episulfide.

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

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

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

1. "thiirane (CHEBI:30977)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
2. Warren Chew; David N. Harpp (1993). "Recent aspects of thiirane chemistry". Journal of Sulfur Chemistry. 15 (1): 1–39. doi:10.1080/01961779308050628.
3. Wataru Ando; Nami Choi; Norihiro Tokitoh (1996). "Thiiranes and Thiirenes: Monocyclic". Comprehensive Heterocyclic Chemistry II. Vol. 1A. pp. 173–240. doi:10.1016/B978-008096518-5.00005-8. ISBN   978-0-08-096518-5.
4. De Vos, John; Schröder, Benjamin; Rauhut, Guntram (2023-12-05). "Comprehensive quantum chemical analysis of the (ro)vibrational spectrum of thiirane and its deuterated isotopologue". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 302: 123083. doi:10.1016/j.saa.2023.123083. ISSN   1386-1425.
5. Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. (1962). "Ethylene Sulfide". Organic Syntheses. 42: 59. doi: 10.15227/orgsyn.042.0059 .
6. R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). ISBN   0-471-95512-4.
7. Gunars Zelans; Jacquelyn Gervay-Hague; Ivy Maulie (2010). "Ethylene Sulfide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.re079.pub2. ISBN   978-0-471-93623-7.