Thiirane

Formula: C₂H₄S
Molecular weight: 60.118
IUPAC Standard InChI: InChI=1S/C2H4S/c1-2-3-1/h1-2H2
IUPAC Standard InChIKey: VOVUARRWDCVURC-UHFFFAOYSA-N
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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Gas phase thermochemistry data

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Data compiled by: Donald R. Burgess, Jr.

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	19.7 ± 0.24	kcal/mol	N/A	Sunner, 1963	Value computed using Δ_fH_liquid° value of 52±1 kj/mol from Sunner, 1963 and Δ_vapH° value of 30.3±0.2 kj/mol from missing citation.

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	12.4 ± 0.3	kcal/mol	Ccr	Sunner, 1963	See Sunner, 1962
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-481.02	kcal/mol	Ccr	Sunner, 1963	See Sunner, 1962

Vibrational and/or electronic energy levels

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Data compiled by: Marilyn E. Jacox

State: X

Vib. sym.	No.	Approximate type of mode	cm^-1		Med.	Method	References


a₁	1	CH stretch	3207	w	Ar	IR	Krantz and Laureni, 1977 Torres, Clement, et al., 1978 Torres, Safarik, et al., 1979
	1	CH stretch	3202		N₂	IR	Krantz and Laureni, 1981
	2	C=C stretch	1663	w	Ar	IR	Laureni, Krantz, et al., 1976 Krantz and Laureni, 1977 Torres, Clement, et al., 1978 Torres, Safarik, et al., 1979
	2	C=C stretch	1660		N₂	IR	Krantz and Laureni, 1981
	4	C-S stretch	657	m T	Ar	IR	Torres, Clement, et al., 1978 Torres, Safarik, et al., 1979 Hawkins, Almond, et al., 1985
b₁	6	OPLA	563	m	Ar	IR	Laureni, Krantz, et al., 1976 Krantz and Laureni, 1977 Torres, Clement, et al., 1978 Torres, Safarik, et al., 1979 Hawkins, Almond, et al., 1985
	6	OPLA	570		N₂	IR	Krantz and Laureni, 1981
b₂	7	CH stretch	3169	m	Ar	IR	Laureni, Krantz, et al., 1976 Krantz and Laureni, 1977 Torres, Clement, et al., 1978 Torres, Safarik, et al., 1979
	7	CH stretch	3166	m	Ar	IR	Laureni, Krantz, et al., 1976 Krantz and Laureni, 1977 Torres, Clement, et al., 1978 Torres, Safarik, et al., 1979
	7	CH stretch	3161		N₂	IR	Krantz and Laureni, 1981
	8	CH deform.	912	m	Ar	IR	Laureni, Krantz, et al., 1976 Krantz and Laureni, 1977 Torres, Clement, et al., 1978 Torres, Safarik, et al., 1979 Hawkins, Almond, et al., 1985
	8	CH deform.	910		N₂	IR	Krantz and Laureni, 1981

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

Notes

Weak

Medium

Tentative assignment or approximate value

References

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Sunner, 1963
Sunner, S., Corrected heat of combustion and formation values for a number of organic sulphur compounds, Acta Chem. Scand., 1963, 17, 728-730. [all data]

Sunner, 1962
Sunner, S., Corrected heat of combustion and formation values for a number of organic sulphur compounds, Private communication, 1962, 1-4. [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]

Notes

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Symbols used in this document:

Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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