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. ^ a b "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.
Allikas: https://en.wikipedia.org/wiki/Thiirane
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