Thiirane, methyl-

Formula: C₃H₆S
Molecular weight: 74.145
IUPAC Standard InChI: InChI=1S/C3H6S/c1-3-2-4-3/h3H,2H2,1H3
IUPAC Standard InChIKey: MBNVSWHUJDDZRH-UHFFFAOYSA-N
CAS Registry Number: 1072-43-1
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: Propane, 1,2-epithio-; Propene sulfide; Propylene episulfide; Propylene sulfide; 1,2-Epithiopropane; Methylthiirane; Thiirane, 2-methyl-; 2-Methylthiacyclopropane; 2-Methylthiirane; Propylene sulphide; NSC 36643; NSC 48100
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Information on this page:
Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
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Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity	Value	Units	Method	Reference	Comment
T_boil	345.7	K	N/A	Weast and Grasselli, 1989	BS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
34.6	287.	A	Stephenson and Malanowski, 1987	Based on data from 272. to 423. K. See also Dykyj, 1970 and Dykyj, Svoboda, et al., 1999.; AC

Gas phase ion energetics data

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

Data compiled as indicated in comments:
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 C₃H₆S⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	833.3	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	801.5	kJ/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.85	PI	Traeger, 1984	LBLHLM
8.7	PE	Aue and Bowers, 1979	LLK
8.6 ± 0.2	EI	Hobrock and Kiser, 1962	RDSH
8.88	PE	McAlduff and Houk, 1977	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CHS⁺	14.1 ± 0.2	?	EI	Hobrock and Kiser, 1962	RDSH
CH₂S⁺	12.4 ± 0.3	?	EI	Hobrock and Kiser, 1962	RDSH
CH₃⁺	18.1 ± 0.4	?	EI	Hobrock and Kiser, 1962	RDSH
CH₃S⁺	13.5 ± 0.2	?	EI	Hobrock and Kiser, 1962	RDSH
C₂H₂⁺	17.7 ± 0.4	?	I	Hobrock and Kiser, 1962	RDSH
C₂H₂S⁺	15.6 ± 0.4	?	EI	Hobrock and Kiser, 1962	RDSH
C₂H₃⁺	17.2 ± 0.3	?	EI	Hobrock and Kiser, 1962	RDSH
C₂H₃S⁺	12.3 ± 0.3	?	EI	Hobrock and Kiser, 1962	RDSH
C₃H⁺	22.2 ± 0.5	?	EI	Hobrock and Kiser, 1962	RDSH
C₃H₂⁺	19.2 ± 0.4	?	EI	Hobrock and Kiser, 1962	RDSH
C₃H₃⁺	15.9 ± 0.2	?	EI	Hobrock and Kiser, 1962	RDSH
C₃H₄⁺	14.4 ± 0.3	?	EI	Hobrock and Kiser, 1962	RDSH
C₃H₅⁺	10.66	SH	PI	Traeger, 1984	LBLHLM
C₃H₅⁺	11.5 ± 0.2	SH?	EI	Hobrock and Kiser, 1962	RDSH
C₃H₅S⁺	11.2 ± 0.3	H	EI	Hobrock and Kiser, 1962	RDSH

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Apiezon M	130.	659.	Garbuzov, Misharina, et al., 1985	He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	875.	Cha, Kim, et al., 1998	60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 3. K/min, 200. C @ 60. min
Capillary	CP-Wax 52CB	924.	Yu, Wu, et al., 1989	N2, 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; T_start: 50. C; T_end: 200. C
Capillary	CP-Wax 52CB	924.	Yu, Wu, et al., 1989, 2	N2, 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; T_start: 50. C; T_end: 200. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	OV-101	651.	Zenkevich, 2005	25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; T_start: 50. C; T_end: 250. C
Capillary	DB-5	650.	Macku and Shibamoto, 1991	He, 40. C @ 5. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 160. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	VF-5	652.	Shivashankar, Roy, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (2 min) 3 0C/min -> 200 0C (3 min) 10 0C/min -> 220 0C (8 min)
Capillary	VF-5	650.	Shivashankar, Roy, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	HP-5	637.	Rotsatschakul, Visesanguan, et al., 2009	60. m/0.25 mm/0.25 μm, Helium; Program: 30 0C (2 min) 2 0Cmin -> 60 0C 10 0C/min -> 100 0C 20 0C/min -> 140 0C 10 0C/min -> 200 0C (10 min)
Capillary	HP-5 MS	606.	Pyun and Shin, 2006	30. m/0.25 mm/0.25 μm; Program: 40 0C (3 min) 2 0C/min -> 150 0C 20 0C/min -> 220 0C (5 min)
Capillary	Methyl Silicone	651.	Farkas, Héberger, et al., 2004	Program: not specified
Capillary	DB-5	619.	Mateo and Zumalacárregui, 1996	50. m/0.32 mm/0.25 μm, He; Program: 40C (10min) => 3C/min => 95C => 10C/min => 270C (10min)

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Supelcowax-10	900.	Girard and Durance, 2000	60. m/0.25 mm/0.25 μm, He, 35. C @ 10. min, 4. K/min; T_end: 200. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	915.	Gyawalia, Seo, et al., 2006	60. m/0.2 mm/0.25 μm, He; Program: 40C(3min) => 2C/min => 150C => 4C/min => 220C(20min) => 5C/min => 230C

References

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Dykyj, 1970
Dykyj, J., Petrochemica, 1970, 10, 2, 51. [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]

Traeger, 1984
Traeger, J.C., Heat of formation for the SH radical by photoionization mass spectrometry, Org. Mass Spectrom., 1984, 19, 514. [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]

Hobrock and Kiser, 1962
Hobrock, B.G.; Kiser, R.W., Electron impact spectroscopy of propylene sulfide, J. Phys. Chem., 1962, 66, 1551. [all data]

McAlduff and Houk, 1977
McAlduff, E.J.; Houk, K.N., Photoelectron spectra of substituted oxiranes and thiiranes. Substituent effects on ionization potentials involving σ orbitals, Can. J. Chem., 1977, 55, 318. [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]

Cha, Kim, et al., 1998
Cha, Y.J.; Kim, H.; Cadwallader, K.R., Aroma-active compounds in Kimchi during fermentation, J. Agric. Food Chem., 1998, 46, 5, 1944-1953, https://doi.org/10.1021/jf9706991 . [all data]

Yu, Wu, et al., 1989
Yu, T.-H.; Wu, C.-M.; Liou, Y.-C., Volatile compounds from garlic, J. Agric. Food Chem., 1989, 37, 3, 725-730, https://doi.org/10.1021/jf00087a032 . [all data]

Yu, Wu, et al., 1989, 2
Yu, T.-H.; Wu, C.-M.; Chen, S.-Y., Effects of pH adjustment and heat treatment on the stability and the formation of volatile compounds of garlic, J. Agric. Food Chem., 1989, 37, 3, 730-734, https://doi.org/10.1021/jf00087a033 . [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]

Shivashankar, Roy, et al., 2012
Shivashankar, S.; Roy, T.K.; Moorthy, P.N.R., Headspace solid phase micro extraction and GC/MS analysis of the volatile components in seed and cake of Azadirachta indica A. juss, Chem. Bull. of Politechnika Univ. Timisoara, Romania, 2012, 57(71), 1, 1-6. [all data]

Rotsatschakul, Visesanguan, et al., 2009
Rotsatschakul, P.; Visesanguan, W.; Smitinont, T.; Chaiseri, S., Changes in volatile compounds during fermentation of nham (Thai fermented sausage), Int. Food Res. J., 2009, 16, 391-414. [all data]

Pyun and Shin, 2006
Pyun, M.-S.; Shin, S., Antifungal effects of the volatile oils from Allium plants against Trichophyton species and synergism of the oils with ketoconazole, Phytomedicine, 2006, 13, 6, 394-400, https://doi.org/10.1016/j.phymed.2005.03.011 . [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]

Mateo and Zumalacárregui, 1996
Mateo, J.; Zumalacárregui, J.M., Volatile compounds in chorizo and their changes during ripening, Meat Sci., 1996, 44, 4, 255-273, https://doi.org/10.1016/S0309-1740(96)00028-9 . [all data]

Girard and Durance, 2000
Girard, B.; Durance, T., Headspace volatiles of sockeye and pink salmon as affected by retort process, Food Chem. Toxicol., 2000, 65, 1, 34-39. [all data]

Gyawalia, Seo, et al., 2006
Gyawalia, R.; Seo, H.-Y.; Lee, H.-J.; Song, H.-P.; Kim, D.-H.; Byun, M.-W.; Kim, K.-S., Effect of γ-irradiation on volatile compounds of dried Welsh onion (Allium fistulosum L.), Radiat. Phys. Chem., 2006, 75, 2, 322-328, https://doi.org/10.1016/j.radphyschem.2005.07.001 . [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

T_boil Boiling point

Δ_vapH Enthalpy of vaporization
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
T_boil	Boiling point
Δ_vapH	Enthalpy of vaporization