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
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• 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
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • 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

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of fusion

Entropy of fusion

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

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

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

Lee, 1986
Lee, F.-M., Use of Organic Sulfones as the Extractive Distillation SOlvent for Aromatic Recovery, Ind. Eng. Chem. Process Des. Dev., 1986, 25, 949-57. [all data]

Clever and Westrum, 1970, 2
Clever, H.L.; Westrum, E.F., Dimethyl sulfoxide and dimethyl sulfone. Heat capacities, enthalpies of fusion, and thermodynamic properties., J. Phys. Chem., 1970, 74, 1309. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Dykyj, 1970
Dykyj, J., Petrochemica, 1970, 10, 2, 51. [all data]

Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R., Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

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]

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)
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

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