Thiirane
- Formula: C2H4S
- Molecular weight: 60.118
- 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 328.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 328.9 | K | N/A | Lecat, 1947 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 329. | K | N/A | Jones and Reid, 1938 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.24 | kcal/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 7.24 ± 0.05 | kcal/mol | V | Guthrie, Scott, et al., 1952 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.29 | 306. | A | Stephenson and Malanowski, 1987 | Based on data from 291. to 361. K. See also Guthrie, Scott, et al., 1952, 2 and Dykyj, Svoboda, et al., 1999.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
291.44 to 360.88 | 4.15055 | 1190.802 | -41.175 | Guthrie, Scott, et al., 1952, 2 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, References, Notes
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 193.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 185.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.05 | PIPECO | Butler and Baer, 1983 | LBLHLM |
9.04 ± 0.01 | PI | Butler and Baer, 1982 | LBLHLM |
8.9 ± 0.1 | PE | Aue, Webb, et al., 1980 | LLK |
8.9 | PE | Aue and Bowers, 1979 | LLK |
9.00 | PE | Schweig and Thiel, 1973 | LLK |
9.051 ± 0.006 | S | Basco and Morse, 1973 | LLK |
8.87 ± 0.15 | EI | Gallegos and Kiser, 1961 | RDSH |
9.0 | EI | Vorob'ev, Furlei, et al., 1989 | Vertical value; LL |
9.05 | PE | Frost, Herring, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHS+ | 11.07 ± 0.04 | CH3 | PI | Butler and Baer, 1982 | T = 298K; LBLHLM |
CHS+ | 11.13 ± 0.04 | CH3 | PI | Butler and Baer, 1982 | T = 0K; LBLHLM |
CHS+ | 12.3 ± 0.2 | CH3 | EI | Gallegos and Kiser, 1961 | RDSH |
CH2+ | 20.4 ± 0.5 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
CH2S+ | 12.7 ± 0.2 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H2+ | 17.9 ± 0.5 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H2S+ | 15.0 ± 0.2 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H3+ | 14.0 | SH | EI | Haney and Franklin, 1968 | RDSH |
C2H3S+ | 10.7 | H | PIPECO | Butler and Baer, 1983 | LBLHLM |
C2H3S+ | 11.4 ± 0.2 | H | EI | Gallegos and Kiser, 1961 | RDSH |
H2S+ | 13.4 | C2H2 | EI | Haney and Franklin, 1968 | RDSH |
H2S+ | 13.4 ± 0.1 | C2H2 | EI | Gallegos and Kiser, 1961 | RDSH |
S+ | 13.1 ± 0.2 | C2H4 | EI | Gallegos and Kiser, 1961 | RDSH |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon M | 130. | 606. | Garbuzov, Misharina, et al., 1985 | He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 588. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Capillary | DB-5 | 589. | Macku and Shibamoto, 1991 | He, 40. C @ 5. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 160. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 588. | Farkas, Héberger, et al., 2004 | Program: not specified |
Capillary | CP Sil 5 CB | 606. | Gijs, Piraprez, et al., 2000 | 50. m/0.32 mm/1.2 μm, He; Program: 33C (16.5min) => 2C/min => 160C => 20C/min => 200C (9min) |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 899. | Horiuchi, Umano, et al., 1998 | 60. m/0.25 mm/1. μm, He, 3. K/min, 200. C @ 40. min; Tstart: 50. C |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Lecat, 1947
Lecat, M.,
Orthobaric Azeotropes of Sulfides,
Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]
Jones and Reid, 1938
Jones, S.O.; Reid, E.E.,
The Addition of Sulfurl, Hydrogen Sulfide and Mercaptans to Unsaturated Hydrocarbons,
J. Am. Chem. Soc., 1938, 60, 2452. [all data]
Reid, 1972
Reid, Robert C.,
Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00,
AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637
. [all data]
Guthrie, Scott, et al., 1952
Guthrie, G.B., Jr.; Scott, D.W.; Waddington, G.,
Thiacyclopropane (ethylene sulfide): Infrared spectrum, vapor pressure and some thermodynamic properties,
J. Am. Chem. Soc., 1952, 74, 2795-28. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Guthrie, Scott, et al., 1952, 2
Guthrie, G.B.; Scott, D.W.; Waddington, Guy,
Thiacyclopropane (Ethylene Sulfide): Infrared Spectrum, Vapor Pressure and Some Thermodynamic Properties 1,
J. Am. Chem. Soc., 1952, 74, 11, 2795-2800, https://doi.org/10.1021/ja01131a028
. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]
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]
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, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.