Dimethyl Sulfoxide

• Formula: C₂H₆OS
• Molecular weight: 78.133
• IUPAC Standard InChI: InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 Copy

  
• IUPAC Standard InChIKey: IAZDPXIOMUYVGZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 67-68-5
• 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:
  • Dimethylsulfoxide-D6
• Other names: DMSO; Methane, sulfinylbis-; Methyl sulfoxide; Demsodrox; Dimexide; Dipirartril-tropico; Dolicur; Dromisol; Durasorb; DMS 70; DMS 90; Hyadur; Infiltrina; Somipront; Sulfinylbismethane; SQ 9453; Dimethyl sulphoxide; (CH3)2SO; A 10846; Deltan; Demasorb; Demavet; Demeso; Dermasorb; Doligur; Domoso; Gamasol 90; M 176; Methylsulfinylmethane; Rimso 50; Syntexan; NSC-763; Topsym; Dimethyl sulfur oxide; Herpid; Kemsol; Sclerosol; Sulfoxide, dimethyl; Methane, 1,1'-sulfinylbis-; DMSO (methyl sulfoxide); Sulphinylbis methane
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• 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:
  • 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.

Condensed phase thermochemistry data

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

Phase change data

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Enthalpy of fusion

Entropy of fusion

Gas phase ion energetics data

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

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C₂H₆OS⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₂H₅OS^- +  =

By formula: C₂H₅OS^- + H⁺ = C₂H₆OS

Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

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.

Masuda, Nagano, et al., 1994
Masuda, N.; Nagano, Y.; Sakiyama, M., Standard molar enthalpy of formation of (CH₃)₂SO, dimethylsulfoxide, by combustion calorimetry, J. Chem. Thermodyn., 1994, 26, 971-975. [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]

Grolier, Roux-Desgranges, et al., 1993
Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E., Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide, J. Chem. Thermodynam., 1993, 25(1), 41-50. [all data]

Barta, Kooner, et al., 1989
Barta, L.; Kooner, Z.S.; Hepler, L.G.; Roux-Desgranges, G.; Grolier, J.-P.E., Thermal and volumetric properties of chloroform dimethylsulfoxide: Thermodynamic analysis using the ideal associated solution model, J. Solution Chem., 1989, 18(7), 663-673. [all data]

Rodante and Marrosu, 1988
Rodante, F.; Marrosu, G., Excess molar isobaric heat capacities and excess molar enthalpies for water-dimethylsulfoxide mixtures at 25°C, Thermochim. Acta, 1988, 136, 209-218. [all data]

Lankford and Criss, 1987
Lankford, J.I.; Criss, C.M., Partial molar heat caqpacities of selected electrolytes and benzene in methanol and dimethyldulfoxide at 25, 40 and 80°C, J. Solution Chem., 1987, 16(11), 885-906. [all data]

de Visser and Somsen, 1979
de Visser, C.; Somsen, G., Thermochemical behavior of mixtures of N,N-dimethylformamide with dimethylsulfoxide, acetonitrile, and N-methylformamide: volumes and heat capacities, J. Solution Chem., 1979, 8, 593-600. [all data]

De Visser, Heuvelsland, et al., 1978
De Visser, C.; Heuvelsland, W.J.M.; Dunn, L.A.; Somsen, G., Some properties of binary aqueous liquid mixtures, J. Chem. Soc., Faraday Trans.1, 1978, 74, 1159-1169. [all data]

Kenttmaa and Lindberg, 1960
Kenttmaa, J.; Lindberg, J.J., Volumes and heats of mixing of dimethyl sulfoxide-water solutions, Suom. Kemistilehti, 1960, B33, 32-35. [all data]

Lindberg and Stenholm, 1966
Lindberg, J.J.; Stenholm, V., Viscosities, Densities, and Related Properties of Binary Mixtures Containing Dimethyl Sulphoxide and Mono-Subst. Benzenes or Guaiacol, Suom. Kemistiseuran Tied., 1966, 75, 22. [all data]

Douglas, 1948
Douglas, T.B., Vapor Pressure of Methyl Sulfoxide from 20 to 50 deg. Calculation of the Heat of Vaporization, J. Am. Chem. Soc., 1948, 70, 2001. [all data]

Douglas, 1946
Douglas, T.B., Heats of Formation of Liquid Methyl Sulfoxide and Crystalline Methyl Sulfone at 18 deg., J. Am. Chem. Soc., 1946, 68, 1072. [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]

Douglas, 1948, 2
Douglas, T.B., Vapor pressure of methyl sulfoxide from 20 to 50°. Calculation of the heat of vaporization, J. Am. Chem. Soc., 1948, 70, 2001-20. [all data]

Douglas, 1948, 3
Douglas, Thomas B., Vapor Pressure of Methyl Sulfoxide from 20 to 50°. Calculation of the Heat of Vaporization, J. Am. Chem. Soc., 1948, 70, 6, 2001-2002, https://doi.org/10.1021/ja01186a005 . [all data]

Al-Najjar and Al-Sammerrai, 2007
Al-Najjar, Hazim; Al-Sammerrai, Dhoaib, Thermogravimetric determination of the heat of vaporization of some highly polar solvents, J. Chem. Technol. Biotechnol., 2007, 37, 3, 145-152, https://doi.org/10.1002/jctb.280370302 . [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]

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]

Sassa, Konishi, et al., 1974
Sassa, Yoshimasa; Konishi, Ryoichi; Katayama, Takashi, Isothermal vapor-liquid equilibrium data of DMSO [dimethyl sulfoxide] solutions by total pressure method. DMSO-acetone, DMSO-tetrahydrofuran, and DMSO-ethyl acetate systems, J. Chem. Eng. Data, 1974, 19, 1, 44-48, https://doi.org/10.1021/je60060a004 . [all data]

Jakli and Alexander Van Hook, 1972
Jakli, Gyorgy; Alexander Van Hook, W., The vapor pressures of dimethyl sulfoxide and hexadeuterodimethyl sulfoxide from about 313 to 453 K, The Journal of Chemical Thermodynamics, 1972, 4, 6, 857-864, https://doi.org/10.1016/0021-9614(72)90007-9 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

NISHIMURA, NAKAYAMA, et al., 1972
NISHIMURA, MICHIKO; NAKAYAMA, MUTSUO; YANO, TAKEO, VAPOR PRESSURE OF PURE DMSO AND VAPOR-LIQUID EQUILIBRIA IN DMSO-H2O SYSTEM UNDER ISOBARIC CONDITIONS, J. Chem. Eng. Japan / JCEJ, 1972, 5, 3, 223-226, https://doi.org/10.1252/jcej.5.223 . [all data]

Meszaros, 1969
Meszaros, S., Period. Polytech., Chem. Eng., 1969, 13, 1-2, 79. [all data]

Jakli and van Hook, 1972
Jakli, G.; van Hook, W.A., The Vapor Pressures of Dimethyl Sulfoxide and Hexadeuterodimethyl Sulfoxide from about 313 to 453 K, J. Chem. Thermodyn., 1972, 4, 6, 857-864, https://doi.org/10.1016/0021-9614(72)90007-9 . [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]

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]

Hammer, Diri, et al., 2003
Hammer, N.I.; Diri, K.; Jordan, K.D.; Desfrancois, C.; Compton, R.N., Dipole-bound anions of carbonyl, nitrile, and sulfoxide containing molecules, J. Chem. Phys., 2003, 119, 7, 3650-3660, https://doi.org/10.1063/1.1590959 . [all data]

Suess, Liu, et al., 2003
Suess, L.; Liu, Y.; Parthasarathy, R.; Dunning, F.B., Dipole-bound negative ions: Collisional destruction and blackbody-radiation-induced photodetachment, J. Chem. Phys., 2003, 119, 24, 12890-12894, https://doi.org/10.1063/1.1628215 . [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]

Potzinger, Stracke, et al., 1975
Potzinger, P.; Stracke, H.-U.; Kupper, W.; Gollnick, K., Ionisierungs- und Auftrittspotentialmessungen an Dialkylsulfoxiden, Z. Naturforsch. A:, 1975, 30, 340. [all data]

Distefano, Foffani, et al., 1971
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S., Mass spectrometric study of transition metal complexes with ligands having nitrogen or sulphur as donor atom, Adv. Mass Spectrom., 1971, 5, 696. [all data]

Distefano, Foffani, et al., 1971, 2
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S., Electron impact ionization potentials of some manganese, chromium and tungsten organometallic derivatives, Int. J. Mass Spectrom. Ion Phys., 1971, 7, 383. [all data]

Blais, Cottin, et al., 1970
Blais, J.-C.; Cottin, M.; Gitton, B., Ionisation positive et negative dans le dimethylsulfoxyde en phase gazeuse, J. Chim. Phys., 1970, 67, 1475. [all data]

Bock and Solouki, 1974
Bock, H.; Solouki, B., Photoelektronenspektren und molekuleigenschaften, XXXV. Sulfoxide X₂SO - beispiele fur den nutzen von korrelations - diagrammen bei der diskussion von substituenteneffekten und von geometrischen storungen, Chem. Ber., 1974, 107, 2299. [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]

Bock and Solouki, 1972
Bock, H.; Solouki, B., The sulfoxide bond, Angew. Chem. Int. Ed. Engl., 1972, 11, 436. [all data]

Zha, Nishimura, et al., 1988
Zha, Q.; Nishimura, T.; Meisels, G.G., Unimolecular dissociation of energy-selected dimethyl sulfoxide, Int. J. Mass Spectrom. Ion Processes, 1988, 83, 1. [all data]

Amos, Gillis, et al., 1969
Amos, D.; Gillis, R.G.; Occolowitz, J.L.; Pisani, J.F., The ions [CH₃S]⁺, [C₂H₅S]⁺ and [CH₃O]⁺ formed by electron-impact, Org. Mass Spectrom., 1969, 2, 209. [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, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  EA	Electron affinity
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid 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
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization 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.