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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry 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
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Condensed phase 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

Condensed phase thermochemistry data

Go To: Top, Gas phase 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 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

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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, Gas phase thermochemistry data, Condensed phase 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.

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]

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]

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]

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

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

• 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°gas	Enthalpy of formation of gas 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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.