Sulfide, allyl methyl

• Formula: C₄H₈S
• Molecular weight: 88.171
• IUPAC Standard InChI: InChI=1S/C4H8S/c1-3-4-5-2/h3H,1,4H2,2H3 Copy

  
• IUPAC Standard InChIKey: NVLPQIPTCCLBEU-UHFFFAOYSA-N Copy
• CAS Registry Number: 10152-76-8
• 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: 1-Propene, 3-(methylthio)-; Allyl methyl sulfide; Methyl allyl sulfide; 3-(Methylthio)propene; CH3SCH2CH=CH2; 3-(Methylsulfanyl)-1-propene; 3-(Methylthio)-1-propene; Methyl 2-propenyl sulfide; Methyl allyl sulphide; allyl methyl sulphide
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Phase change data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Reaction thermochemistry 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 compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

C₄H₇S^- +  =

By formula: C₄H₇S^- + H⁺ = C₄H₈S

=

By formula: C₄H₈S = C₄H₈S

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 compiled as indicated in comments:
B - John E. Bartmess
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 C₄H₈S⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₇S^- +  =

By formula: C₄H₇S^- + H⁺ = C₄H₈S

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

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

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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

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Van Den Dool and Kratz RI, polar column, custom temperature program

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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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References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes

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

Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R., Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions, J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008 . [all data]

Kimmelma, 1988
Kimmelma, R., Structure-stability relationships in vinyl sulfides. III. Stabilization caused by different alkylthio and phenylthio groups attached to an olefinic double bond, Acta Chem. Scand., 1988, 42, 550-555. [all data]

Schafer and Schweig, 1972
Schafer, W.; Schweig, A., Evidence against the significance of C-S hyperconjugation in determining the conformation of allyl methyl sulphide, J. Chem. Soc., Chem. Commun., 1972, 824. [all data]

Hobrock and Kiser, 1963
Hobrock, B.G.; Kiser, R.W., Electron impact investigations of sulfur compounds. II. 3-Methyl-2-thiabutane, 4-thia-1-pentene, and 3,4-dithiahexane, J. Phys. Chem., 1963, 67, 648. [all data]

Eaton and Traylor, 1974
Eaton, D.F.; Traylor, T.G., Distortional stabilization in phenyl participations, J. Am. Chem. Soc., 1974, 96, 7109. [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]

Golovnya, Misharina, et al., 1978
Golovnya, R.V.; Misharina, T.A.; Garbuzov, V.G., Gas chromatographic characterization of sulfur-containing compounds. 4. The effect of unsaturated radicals on the retention indices of the vinyl, allyl, and propargyl alkyl sulfides, Izv. Akad. Nauk SSSR Ser. Khim., 1978, 11, 2266-2270. [all data]

Yu, Lin, et al., 1994
Yu, T.-H.; Lin, L.-Y.; Ho, C.-T., Volatile compounds of blanched, fried blanched, and baked blanched garlic slices, J. Agric. Food Chem., 1994, 42, 6, 1342-1347, https://doi.org/10.1021/jf00042a018 . [all data]

Schreyen, Dirinck, et al., 1976
Schreyen, L.; Dirinck, P.; van Wassenhove, F.; Schamp, N., Volatile flavor components of leek, J. Agric. Food Chem., 1976, 24, 2, 336-341, https://doi.org/10.1021/jf60204a056 . [all data]

Mochizuki, Yamamoto, et al., 1998
Mochizuki, E.; Yamamoto, T.; Komiyama, Y.; Nakazawa, H., Identification of allium products using flame photometric detection gas chromatography and distribution patterns of volatile sulfur compounds, J. Agric. Food Chem., 1998, 46, 12, 5170-5176, https://doi.org/10.1021/jf9803076 . [all data]

Calvo-Gómez, Morales-López, et al., 2004
Calvo-Gómez, O.; Morales-López, J.; López, M.G., Solid-phase microextraction-gas chromatographic-mass spectrometric analysis of garlic oil obtained by hydrodistillation, J. Chromatogr. A, 2004, 1036, 1, 91-93, https://doi.org/10.1016/j.chroma.2004.02.072 . [all data]

Storsberg, Schulz, et al., 2004
Storsberg, J.; Schulz, H.; Keusgen, M.; Tannous, F.; Dehmer, K.J.; Joachim Keller, E.R., Chemical characterization of interspecific hybrids between Allium cepa L. and Allium kermesinum Rchb., J. Agric. Food Chem., 2004, 52, 17, 5499-5505, https://doi.org/10.1021/jf049684a . [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]

Kim, Wu, et al., 1995
Kim, S.M.; Wu, C.M.; Kubota, K.; Kobayashi, A., Effect of soybean oil on garlic volatile compounds isoalted by distillation, J. Agric. Food Chem., 1995, 43, 2, 449-452, https://doi.org/10.1021/jf00050a036 . [all data]

Yu, Wu, et al., 1993
Yu, T.-H.; Wu, C.-M.; Ho, C.-T., Volatile compounds of deep-oil fried, microwave-heated, and oven-baked garlic slices, J. Agric. Food Chem., 1993, 41, 5, 800-805, https://doi.org/10.1021/jf00029a023 . [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]

Bianchi, Cantoni, et al., 2007
Bianchi, F.; Cantoni, C.; Careri, M.; Chiesa, L.; Musci, M.; Pinna, A., Characterization of the aromatic profile for the authentication and differentiation of typical Italian dry-sausages, Talanta, 2007, 72, 4, 1552-1563, https://doi.org/10.1016/j.talanta.2007.02.019 . [all data]

Bianchi, Careri, et al., 2007
Bianchi, F.; Careri, M.; Mangia, A.; Musci, M., Retention indices in the analysis of food aroma volatile compounds in temperature-programmed gas chromatography: Database creation and evaluation of precision and robustness, J. Sep. Sci., 2007, 39, 4, 563-572, https://doi.org/10.1002/jssc.200600393 . [all data]

Meynier, Novelli, et al., 1999
Meynier, A.; Novelli, E.; Chissolinim, R.; Zanardi, E.; Gandemer, G., Volatile compounds of commercial Milano salami, Meat Sci., 1999, 51, 2, 175-183, https://doi.org/10.1016/S0309-1740(98)00122-3 . [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]

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]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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