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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Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
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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)	199.2	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	191.6	kcal/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

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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

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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

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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

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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

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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, Gas phase ion energetics data, Gas Chromatography, Notes

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

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Symbols used in this document:

AE Appearance energy
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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