Dimethyl sulfide

• Formula: C₂H₆S
• Molecular weight: 62.134
• IUPAC Standard InChI: InChI=1S/C2H6S/c1-3-2/h1-2H3 Copy

  
• IUPAC Standard InChIKey: QMMFVYPAHWMCMS-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-18-3
• 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.
• Isotopologues:
  • Methane-d3,(methylthio)
• Other names: Methane, thiobis-; Methyl sulfide; Dimethyl monosulfide; Dimethyl thioether; DMS; Methyl monosulfide; 2-Thiapropane; Dimethyl sulphide; Thiobismethane; (CH3)2S; Dimethylsulfid; Exact-S; Methyl sulphide; Methylthiomethane; Sulfure de methyle; 2-Thiopropane; UN 1164; Methyl thioether; Sulfide, methyl-; Methane, 1,1'-thiobis-; (Methylsulfanyl)methane
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• Options:
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Condensed phase thermochemistry data

Go To: Top, Reaction thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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

C₂H₅S^- +  =

By formula: C₂H₅S^- + H⁺ = C₂H₆S

C₂H₇S⁺ +  = (C₂H₇S⁺ • )

By formula: C₂H₇S⁺ + C₂H₆S = (C₂H₇S⁺ • C₂H₆S)

C₂H₆S⁺ +  = (C₂H₆S⁺ • )

By formula: C₂H₆S⁺ + C₂H₆S = (C₂H₆S⁺ • C₂H₆S)

Bond type: Charge transfer bond (positive ion)

C₄H₉⁺ +  = (C₄H₉⁺ • )

By formula: C₄H₉⁺ + C₂H₆S = (C₄H₉⁺ • C₂H₆S)

2 +  = 2

By formula: 2C₂H₆S + O₂ = 2C₂H₆OS

 +  = ( • )

By formula: Li⁺ + C₂H₆S = (Li⁺ • C₂H₆S)

 +  = ( • )

By formula: Na⁺ + C₂H₆S = (Na⁺ • C₂H₆S)

Free energy of reaction

 +  =  + 

By formula: HI + C₂H₅IS = C₂H₆S + I₂

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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 C₂H₆S⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₂H₅S^- +  =

By formula: C₂H₅S^- + H⁺ = C₂H₆S

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

Voronkov, Klyuchnikov, et al., 1989
Voronkov, M.G.; Klyuchnikov, V.A.; Kolabin, S.N.; Shvets, G.N.; Varusin, P.I.; Deryagina, E.N.; Korchevin, N.A.; Tsvetnitskaya, S.I., Thermochemical properties of diorganyl chalcogenides and dichalcogenides RM_nR(M = S, Se, Te; n = 1, 2)., Dokl. Phys. Chem. (Engl. Transl.), 1989, 307, 650-653, In original 1139. [all data]

McCullough, Hubbard, et al., 1957
McCullough, J.P.; Hubbard, W.N.; Frow, F.R.; Hossenlopp, I.A.; Waddington, G., Ethanethiol and 2-thiapropane: Heats of formation and isomerization; the chemical thermodynamic properties from 0 to 1000°K, J. Am. Chem. Soc., 1957, 79, 561-566. [all data]

Douglas, 1946
Douglas, T.B., Heats of formation of liquid methyl sulfoxide and crystalline methyl sulfone at 18°, J. Am. Chem. Soc., 1946, 68, 1072-1076. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Moran and Ellison, 1988
Moran, S.; Ellison, G.B., Photoelectron Spectroscopy of Sulfur Ions, J. Phys. Chem., 1988, 92, 7, 1794, https://doi.org/10.1021/j100318a021 . [all data]

Ingemann and Nibbering, 1985
Ingemann, S.; Nibbering, N.M.M., Gas phase chemistry of alpha-thio carbanions, Can. J. Chem., 1985, 62, 2273. [all data]

Meot-Ner (Mautner) and Sieck, 1985
Meot-Ner (Mautner), M.; Sieck, L.W., The Ionic Hydrogen Bond and Ion Solvation. 4. SH+ O and NH+ S Bonds. Correlations with Proton Affinity. Mutual Effects of Weak and Strong Ligands in Mixed Clusters, J. Phys. Chem., 1985, 89, 24, 5222, https://doi.org/10.1021/j100270a021 . [all data]

Deng, Illies, et al., 1995
Deng, Y.; Illies, A.J.; James, M.A.; McKee, M.L.; Peschke, M., A Definitive Investigation of the Gas-Phase Two-Center Three-electron Bond in [H2S:SH2+], [Me2S:SMe2]+, and [Et2S:SEt2]+: Therory and Experiment, J. Am. Chem. Soc., 1995, 117, 1, 420, https://doi.org/10.1021/ja00106a048 . [all data]

Meot-Ner (Mautner) and Sieck, 1991
Meot-Ner (Mautner), M.; Sieck, L.W., Proton affinity ladders from variable-temperature equilibrium measurements. 1. A reevaluation of the upper proton affinity range, J. Am. Chem. Soc., 1991, 113, 12, 4448, https://doi.org/10.1021/ja00012a012 . [all data]

Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Shum and Benson, 1985
Shum, L.G.S.; Benson, S.W., Iodine catalyzed pyrolysis of dimethyl sulfide. Heats of formaton of CH₃SCH₂I, the CH₃SCH₂ radical, and the pibond energy in CH₂S, Int. J. Chem. Kinet., 1985, 17, 277-292. [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]

Carnovale, Livett, et al., 1983
Carnovale, F.; Livett, M.K.; Peel, J.B., Identification of the gas phase trimer (CH₃)₂S.(HF)₂ by photoelectron spectroscopy, J. Am. Chem. Soc., 1983, 105, 6788. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [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]

McDiarmid, 1974
McDiarmid, R., Assignments of Rydberg and valence transitions in the electronic absorption spectrum of dimethyl sulfide, J. Chem. Phys., 1974, 61, 274. [all data]

Scott, Causley, et al., 1973
Scott, J.D.; Causley, G.C.; Russell, B.R., Vacuum ultraviolet absorption spectra of dimethylsulfide, dimethylselenide, and dimethyltelluride, J. Chem. Phys., 1973, 59, 6577. [all data]

Mollere, Bock, et al., 1973
Mollere, P.; Bock, H.; Becker, G.; Fritz, G., Photoelectron spectra and molecular properties. XXI. Dimethyl sulfide, methyl silyl sulfide, and disilyl sulfide, J. Organomet. Chem., 1973, 61, 127. [all data]

Bunzli, Frost, et al., 1973
Bunzli, J.C.; Frost, D.C.; Weiler, L., Photoelectron spectrum of 7-thiabicyclo[2.2.1]heptane, J. Am. Chem. Soc., 1973, 95, 7880. [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]

Akopyan, Sergeev, et al., 1970
Akopyan, M.E.; Sergeev, Yu.L.; Vilesov, F.I., Photionization in vapors of aliphatic sulfides. I. Methymercaptan, dimethyl and diethyl sulfides, High Energy Chem., 1970, 4, 265, In original 305. [all data]

Cullen, Frost, et al., 1969
Cullen, W.R.; Frost, D.C.; Vroom, D.A., Ionization potentials of some sulfur compounds, Inorg. Chem., 1969, 8, 1803. [all data]

Keyes and Harrson, 1968
Keyes, B.G.; Harrson, A.G., The fragmentation of aliphatic sulfur compounds by electron impact, J. Am. Chem. Soc., 1968, 90, 5671. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Chang, Young, et al., 1986
Chang, F.C.; Young, V.Y.; Prather, J.W.; Cheng, K.L., Study of methyl chalcogen compounds with ultraviolet photoelectron spectroscopy, J. Electron Spectrosc. Relat. Phenom., 1986, 40, 363. [all data]

Kobayashi, 1978
Kobayashi, T., A new rule for photoelectron angular distributions of molecules, Phys. Lett. A, 1978, 69, 31. [all data]

Kobayashi, 1978, 2
Kobayashi, T., A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes, Phys. Lett., 1978, 69, 105. [all data]

Wagner and Bock, 1974
Wagner, G.; Bock, H., Photoelektronenspektren und molekuleigenschaften, XXVI. Die delokalisation von schwefel-elektronenpaaren in alkylsulfiden und -disulfiden, Chem. Ber., 1974, 107, 68. [all data]

Schweig and Thiel, 1974
Schweig, A.; Thiel, W., Photoionization cross sections: He I- and He II-photoelectron spectra of homologous oxygen and sulphur compounds, Mol. Phys., 1974, 27, 265. [all data]

Frost, Herring, et al., 1972
Frost, D.C.; Herring, F.G.; Katrib, A.; McDowell, C.A.; McLean, R.A.N., Photoelectron spectra of CH₃SH, (CH₃)₂S, C₆H₅SH, and C₆H₅CH₂SH; the bonding between sulfur and carbon, J. Phys. Chem., 1972, 76, 1030. [all data]

Cradock and Whiteford, 1972
Cradock, S.; Whiteford, R.A., Photoelectron spectra of the methyl, silyl and germyl derivatives of the group VI elements, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 281. [all data]

Bock, Wagner, et al., 1972
Bock, H.; Wagner, G.; Kroner, J., Photoelektronenspektren und molekuleigenschaften, XIV. Die delokalisation des schwefel-elektronenpaar in CH₃S-substituierten aromaten, Chem. Ber., 1972, 105, 3850. [all data]

Ermolenko, Akopyan, et al., 1983
Ermolenko, A.I.; Akopyan, M.E.; Sergeev, Y.L., Decomposition of dimethyl sulfide molecular ions. Randomization of states during photoionization dissociation of molecules, High Energy Chem., 1983, 17, 25. [all data]

Cullen, Frost, et al., 1970
Cullen, W.R.; Frost, D.C.; Pun, M.T., Mass spectra, appearance potentials, heats of formation, and bond energies of some alkyl and perfluoroalkyl sulfides, Inorg. Chem., 1970, 9, 1976. [all data]

Gowenlock, Kay, et al., 1963
Gowenlock, B.G.; Kay, J.; Majer, J.R., Electron impact studies of some sulphides and disulphides, J. Chem. Soc. Faraday Trans., 1963, 59, 2463. [all data]

Taft, Martin, et al., 1965
Taft, R.W.; Martin, R.H.; Lampe, F.W., Stabilization energies of substituted methyl cations. The effect of strong demand on the resonance order, J. Am. Chem. Soc., 1965, 87, 2490. [all data]

Haney and Franklin, 1969
Haney, M.A.; Franklin, J.L., Heats of formation of H₃O⁺, H₃S⁺, and NH₄⁺ by electron impact, J. Chem. Phys., 1969, 50, 2028. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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