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:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• Options:
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Phase change data

Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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)

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Enthalpy of fusion

Entropy of fusion

Gas phase ion energetics data

Go To: Top, Phase change data, Gas Chromatography, 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

Gas Chromatography

Go To: Top, 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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

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

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
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]

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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]

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Sassa, Konishi, et al., 1974
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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]

Clever and Westrum, 1970, 2
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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]

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Cumming and Kebarle, 1978
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Cros, Lignot, et al., 2005
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Chung, 1999
Chung, H.Y., Volatile components in crabmeats of Charybdis feriatus, J. Agric. Food Chem., 1999, 47, 6, 2280-2287, https://doi.org/10.1021/jf981027t . [all data]

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Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  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
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