S-Ethyl ethanethioate

• Formula: C₄H₈OS
• Molecular weight: 104.171
• IUPAC Standard InChI: InChI=1S/C4H8OS/c1-3-6-4(2)5/h3H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: APTGPWJUOYMUCE-UHFFFAOYSA-N Copy
• CAS Registry Number: 625-60-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Acetic acid, thio-, S-ethyl ester; Ethyl thiolacetate; S-Ethyl thioacetate; S-Ethyl thiolacetate; Ethanethioic acid, S-ethyl ester; CH3COSC2H5; Ethyl thioacetate
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

 +  =  + 

By formula: C₄H₈OS + H₂O = C₂H₄O₂ + C₂H₆S

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:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₄H₈OS⁺ (ion structure unspecified)

Ionization energy determinations

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, 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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Normal alkane RI, polar column, temperature ramp

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References

Go To: Top, Gas phase thermochemistry data, Phase change data, 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.

Guthrie, 1978
Guthrie, J.P., Hydration of thioesters. Evaluation of the free-energy changes for the addition of water to some thioesters, rate-equilibrium correlations over very wide ranges in equilibrium constants, and a new mechanistic criterion, J. Am. Chem. Soc., 1978, 100, 5892-5904. [all data]

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]

Dunbar and Bolstad, 1955
Dunbar, R.E.; Bolstad, A.N., The Acetylation of Mercaptans with Ketene, J. Am. Chem. Soc., 1955, 77, 4672. [all data]

Wilson, Wilson, et al., 1996
Wilson, L.C.; Wilson, H.L.; Wilding, W.V.; Wilson, G.M., Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method, J. Chem. Eng. Data, 1996, 41, 1252-4. [all data]

Wadsö, Murto, et al., 1966
Wadsö, Ingemar; Murto, Maija-Leena; Bergson, Göran; Ehrenberg, L.; Brunvoll, J.; Bunnenberg, E.; Djerassi, Carl; Records, Ruth, Heats of Vaporization for a Number of Organic Compounds at 25 degrees C., Acta Chem. Scand., 1966, 20, 544-552, https://doi.org/10.3891/acta.chem.scand.20-0544 . [all data]

Wadso, 1966
Wadso, I., Acta Chem. Scand., 1966, 20, 544. [all data]

Wadso, 1957
Wadso, I., The heats of hydrolysis of some alkyl thiolesters, Acta Chem. Scand., 1957, 11, 1745-1751. [all data]

Nagata, Yamabe, et al., 1975
Nagata, S.; Yamabe, T.; Fukui, K., A study of the electronic spectra of thioacetic acid and its ethyl ester, J. Phys. Chem., 1975, 79, 2335. [all data]

Jones, Modelli, et al., 1994
Jones, D.; Modelli, A.; Olivato, P.R.; DalColle, M.; dePalo, M.; Distefano, G., Ab initio and electron spectroscopy study of carbonyl derivatives, J. Chem. Soc. Perkin Trans. 2, 1994, 1994, 1651. [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, Garbuzov, et al., 1981
Golovnya, R.V.; Garbuzov, V.G.; Aérov, A.F., Comparison of the retention indices and differential molar free energies of solution for thiolic and carboxylic esters on gas-chromatographic columns with various polarities, Izv. Akad. Nauk SSSR Ser. Khim., 1981, 10, 1877-1880. [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]

Huynh-Ba, Matthey-Doret, et al., 2003
Huynh-Ba, T.; Matthey-Doret, W.; Fay, L.B.; Rhlid, R.B., Generation of thiols by biotransformation of cysteine-aldehyde conjugates with Baker's yeast, J. Agric. Food Chem., 2003, 51, 12, 3629-3635, https://doi.org/10.1021/jf026198j . [all data]

Weenen, Koolhaas, et al., 1996
Weenen, H.; Koolhaas, W.E.; Apriyantono, A., Sulfur-containing volatiles of durian fruits (Durio zibethinus Murr.), J. Agric. Food Chem., 1996, 44, 10, 3291-3293, https://doi.org/10.1021/jf960191i . [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]

Chin, Nazimah, et al., 2007
Chin, S.T.; Nazimah, S.A.H.; Quek, S.Y.; Che Man, Y.B.; Rahman, R.A.; Hashim, D.M., Analysis of volatile compounds from Malaysian durians (Durio zibethinus) using headspace SPME coupled to fast GC-MS, J. Food Comp. Anal., 2007, 20, 1, 31-44, https://doi.org/10.1016/j.jfca.2006.04.011 . [all data]

Notes

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

• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

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