Dimethyl sulfone

• Formula: C₂H₆O₂S
• Molecular weight: 94.133
• IUPAC Standard InChI: InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3 Copy

  
• IUPAC Standard InChIKey: HHVIBTZHLRERCL-UHFFFAOYSA-N Copy
• CAS Registry Number: 67-71-0
• 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: Methane, sulfonylbis-; MSM; Methyl sulfone; Methylsulfonylmethane; Sulfone, dimethyl-; DMSO2; Sulphonylbismethane; Dimethyl sulphone; Sulfonylbismethane; Methane, 1,1'-sulfonylbis-; NSC 63345; 54841-73-5
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• 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)
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

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
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

C₂H₅O₂S^- +  =

By formula: C₂H₅O₂S^- + H⁺ = C₂H₆O₂S

=  + 0.5

By formula: C₂H₆O₂S = C₂H₆OS + 0.5O₂

 +  = ( • )

By formula: Li⁺ + C₂H₆O₂S = (Li⁺ • C₂H₆O₂S)

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

Ionization energy determinations

De-protonation reactions

C₂H₅O₂S^- +  =

By formula: C₂H₅O₂S^- + H⁺ = C₂H₆O₂S

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.

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]

Busfield, Mackle, et al., 1961
Busfield, W.K.; Mackle, H.; O'Hare, P.A.G., Studies in the thermochemistry of sulphones. Part 2 - The standard heats of formation of sulphones of the type RSO2CH3, Trans. Faraday Soc., 1961, 57, 1054-1057. [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]

Clever and Westrum, 1970
Clever, H.L.; Westrum, E.F., Jr., Dimethylsulfoxide and dimethylsulfone. Heat capacities, enthalpies of fusion, and thermodynamic properties, J. Phys. Chem., 1970, 74, 1309-1317. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Buncel, Decouzon, et al., 1997
Buncel, E.; Decouzon, M.; Formento, A.; Gal, J.-F.; Herreros, M.; Li, L.; Maria, P.-C., Lithium-Cation and Proton Affinities of Sulfoxides and Sulfones: A Fourier Transform Ion Cyclotron Resonance Study, J. Am. Soc. Mass Spectrom., 1997, 8, 3, 262, https://doi.org/10.1016/S1044-0305(96)00255-3 . [all data]

Solouki, Bock, et al., 1975
Solouki, B.; Bock, H.; Appel, R., Photoelektronenspektren und Molekuleigenschaften, XLV Schwefelsaure-Derivate X₂SY₂: Alkyl-, Vinyl- und Arylsulfone, Alkylsulfoimide und Sulfurylhalogenide, Chem. Ber., 1975, 108, 897. [all data]

Muller and Schweig, 1973
Muller, C.; Schweig, A., Konjugation in Sulfonen, Tetrahedron, 1973, 29, 3973. [all data]

Solouki, Bock, et al., 1972
Solouki, B.; Bock, H.; Appel, R., Sequence of orbitals in sulfones and sulfodiimides, Angew. Chem. Int. Ed. Engl., 1972, 11, 927. [all data]

Mines, Thomas, et al., 1972
Mines, G.W.; Thomas, R.K.; Thompson, H., Photoelectron spectra of compounds containing thionyl and sulphuryl groups, Proc. R. Soc. London A:, 1972, 329, 275. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  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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