Thiirane

• Formula: C₂H₄S
• Molecular weight: 60.118
• IUPAC Standard InChI: InChI=1S/C2H4S/c1-2-3-1/h1-2H2 Copy

  
• IUPAC Standard InChIKey: VOVUARRWDCVURC-UHFFFAOYSA-N Copy
• CAS Registry Number: 420-12-2
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Ethylene sulfide; Ethylene episulfide; Thiacyclopropane; Thiirene, 2,3-dihydro-; 2,3-Dihydrothiirene; Ethylene episulphide; Ethylene sulphide; NSC 89690; epithioethane
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• Information on this page:
  • Gas phase ion energetics data
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₂H₄S⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

Vibrational and/or electronic energy levels

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Marilyn E. Jacox

State:   X

Additional references: Jacox, 1994, page 256; Krantz and Laureni, 1979; Allen, Bertie, et al., 1986

Notes

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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References

Go To: Top, Gas phase ion energetics data, Vibrational and/or electronic energy levels, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Butler and Baer, 1983
Butler, J.J.; Baer, T., A photoionization study of organosulfur ring compounds: Thiirane, thietane and tetrahydrothiophene, Org. Mass Spectrom., 1983, 18, 248. [all data]

Butler and Baer, 1982
Butler, J.J.; Baer, T., Photoionization study of the heat of formation of HCS⁺, J. Am. Chem. Soc., 1982, 104, 5016. [all data]

Aue, Webb, et al., 1980
Aue, D.H.; Webb, H.M.; Davidson, W.R.; Vidal, M.; Bowers, M.T.; Goldwhite, H.; Vertal, L.E.; Douglas, J.E.; Kollman, P.A.; Kenyon, G.L., Proton affinities photoelectron spectra of three-membered-ring J. Heterocycl. Chem., J. Am. Chem. Soc., 1980, 102, 5151. [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Schweig and Thiel, 1973
Schweig, A.; Thiel, W., Photoionization cross sections: He I and He II photoelectron spectra of saturated three-membered rings, Chem. Phys. Lett., 1973, 21, 541. [all data]

Basco and Morse, 1973
Basco, N.; Morse, R.D., Analysis of the Rydberg transitions in ethylene sulphide, Chem. Phys. Lett., 1973, 20, 404. [all data]

Gallegos and Kiser, 1961
Gallegos, E.; Kiser, R.W., Electron impact spectroscopy of ethylene sulfide and ethylenimine, J. Phys. Chem., 1961, 65, 1177. [all data]

Vorob'ev, Furlei, et al., 1989
Vorob'ev, A.S.; Furlei, I.I.; Sultanov, A.S.; Khvostenko, V.I.; Leplyanin, G.V.; Derzhinskii, A.R.; Tolstikov, G.A., Mass spectrometry of reasonance capture of electrons and photoelectron spectroscopy of molecules of ethylene oxide, ethylene sulfide, and their derivatives, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 1388. [all data]

Frost, Herring, et al., 1973
Frost, D.C.; Herring, F.G.; Katrib, A.; McDowell, C.A., The photoelectron spectrum of ethylene sulphide, Chem. Phys. Lett., 1973, 20, 401. [all data]

Haney and Franklin, 1968
Haney, M.A.; Franklin, J.L., Correlation of excess energies of electron-impact dissociations with the translational energies of the products, J.Chem. Phys., 1968, 48, 4093. [all data]

Krantz and Laureni, 1977
Krantz, A.; Laureni, J., A methodology for the preparation and characterization of three-membered, potentially antiaromatic molecules. Preparation of matrix-isolated thiirene and selenirene, J. Am. Chem. Soc., 1977, 99, 14, 4842, https://doi.org/10.1021/ja00456a060 . [all data]

Torres, Clement, et al., 1978
Torres, M.; Clement, A.; Bertie, J.E.; Gunning, H.E.; Strausz, O.P., Low-temperature matrix isolation of thiirenes, J. Org. Chem., 1978, 43, 12, 2490, https://doi.org/10.1021/jo00406a045 . [all data]

Torres, Safarik, et al., 1979
Torres, M.; Safarik, I.; Clement, A.; Bertie, J.E.; Strausz, O.P., Nouv. J. Chim., 1979, 3, 365. [all data]

Krantz and Laureni, 1981
Krantz, A.; Laureni, J., Characterization of matrix-isolated antiaromatic three-membered heterocycles. Preparation of the elusive thiirene molecule, J. Am. Chem. Soc., 1981, 103, 3, 486, https://doi.org/10.1021/ja00393a002 . [all data]

Laureni, Krantz, et al., 1976
Laureni, J.; Krantz, A.; Hajdu, R.A., Photolysis of isotopically labeled 1,2,3-selenadiazole and 1,2,3-thiadiazole, J. Am. Chem. Soc., 1976, 98, 24, 7872, https://doi.org/10.1021/ja00440a095 . [all data]

Hawkins, Almond, et al., 1985
Hawkins, M.; Almond, M.J.; Downs, A.J., Photochemistry of low-temperature matrixes containing carbonyl sulfide: reactions of sulfur atoms with the phosphorus trihalides phosphorus trifluoride (PF3) and phosphorus trichloride (PCl3) and the hydrocarbons methane, ethene, and ethyne, J. Phys. Chem., 1985, 89, 15, 3326, https://doi.org/10.1021/j100261a034 . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]

Krantz and Laureni, 1979
Krantz, A.; Laureni, J., The spectrum of matrix-isolated thiirene and characterization of new matrix-isolated species. Comment, J. Org. Chem., 1979, 44, 15, 2730, https://doi.org/10.1021/jo01329a028 . [all data]

Allen, Bertie, et al., 1986
Allen, W.D.; Bertie, J.E.; Falk, M.V.; Hess, B.A., Jr.; Mast, G.B.; Othen, D.A.; Schaad, L.J.; Schaefer, H.F., III, The experimental vibrational spectra, vibrational assignment, and normal coordinate analysis of thiirane-h4 and -d4 and cis- and trans-1,2-dideuteriothiirane: Ab initio theoretical IR spectra of thiirane, thiirene, and isotopically substituted derivatives, J. Chem. Phys., 1986, 84, 8, 4211, https://doi.org/10.1063/1.450043 . [all data]

Garbuzov, Misharina, et al., 1985
Garbuzov, V.G.; Misharina, T.A.; Aerov, A.F.; Golovnya, R.V., Gas chromatographic retention indices for sulphur(II)-containing organic substances, J. Anal. Chem. USSR (Engl. Transl.), 1985, 40, 4, 576-586. [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Macku and Shibamoto, 1991
Macku, C.; Shibamoto, T., Volatile sulfur-containing compounds generated from the thermal interaction of corn oil and cysteine, J. Agric. Food Chem., 1991, 39, 11, 1987-1989, https://doi.org/10.1021/jf00011a021 . [all data]

Farkas, Héberger, et al., 2004
Farkas, O.; Héberger, K.; Zenkevich, I.G., Quantitative structure-retention relationships. XIV. Prediction of gas chromatographic retention indices for saturated O-, N-, and S-heterocyclic compounds, Chemom. Intell. Lab. Syst., 2004, 72, 2, 173-184, https://doi.org/10.1016/j.chemolab.2004.01.012 . [all data]

Gijs, Piraprez, et al., 2000
Gijs, L.; Piraprez, G.; Perpète, P.; Spinnler, E.; Collin, S., Retention of sulfur flavours by food matrix and determination of sensorial data independent of the medium composition, Food Chem., 2000, 69, 3, 319-330, https://doi.org/10.1016/S0956-7135(99)00111-5 . [all data]

Horiuchi, Umano, et al., 1998
Horiuchi, M.; Umano, K.; Shibamoto, T., Analysis of volatile compounds formed from fish oil heated with cysteine and trimethylamine oxide, J. Agric. Food Chem., 1998, 46, 12, 5232-5237, https://doi.org/10.1021/jf980482m . [all data]

Notes

Go To: Top, Gas phase ion energetics data, Vibrational and/or electronic energy levels, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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