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:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 liquid

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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C₂H₅OS^- +  =

By formula: C₂H₅OS^- + H⁺ = C₂H₆OS

 +  = ( • )

By formula: NO₂^- + C₂H₆OS = (NO₂^- • C₂H₆OS)

Free energy of reaction

C₆H₅NO₂^- +  = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₂H₆OS = (C₆H₅NO₂^- • C₂H₆OS)

C₇H₇NO₃^- +  = (C₇H₇NO₃^- • )

By formula: C₇H₇NO₃^- + C₂H₆OS = (C₇H₇NO₃^- • C₂H₆OS)

 +  = ( • )

By formula: Br^- + C₂H₆OS = (Br^- • C₂H₆OS)

 +  = ( • )

By formula: I^- + C₂H₆OS = (I^- • C₂H₆OS)

C₇H₄F₃NO₂^- +  = (C₇H₄F₃NO₂^- • )

By formula: C₇H₄F₃NO₂^- + C₂H₆OS = (C₇H₄F₃NO₂^- • C₂H₆OS)

 +  = ( • )

By formula: Cl^- + C₂H₆OS = (Cl^- • C₂H₆OS)

C₂H₇OS⁺ +  = (C₂H₇OS⁺ • )

By formula: C₂H₇OS⁺ + C₂H₆OS = (C₂H₇OS⁺ • C₂H₆OS)

(C₂H₇OS⁺ • ) +  = (C₂H₇OS⁺ • 2)

By formula: (C₂H₇OS⁺ • C₂H₆OS) + C₂H₆OS = (C₂H₇OS⁺ • 2C₂H₆OS)

( • 4) +  = ( • 5)

By formula: (K⁺ • 4C₂H₆OS) + C₂H₆OS = (K⁺ • 5C₂H₆OS)

( • 5) +  = ( • 6)

By formula: (K⁺ • 5C₂H₆OS) + C₂H₆OS = (K⁺ • 6C₂H₆OS)

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₂H₆OS = (C₆H₄FNO₂^- • C₂H₆OS)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₂H₆OS = (C₆H₄FNO₂^- • C₂H₆OS)

Free energy of reaction

C₆H₄ClNO₂^- +  = (C₆H₄ClNO₂^- • )

By formula: C₆H₄ClNO₂^- + C₂H₆OS = (C₆H₄ClNO₂^- • C₂H₆OS)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₂H₆OS = (C₆H₄FNO₂^- • C₂H₆OS)

Free energy of reaction

C₆H₄ClNO₂^- +  = (C₆H₄ClNO₂^- • )

By formula: C₆H₄ClNO₂^- + C₂H₆OS = (C₆H₄ClNO₂^- • C₂H₆OS)

Free energy of reaction

C₆H₄ClNO₂^- +  = (C₆H₄ClNO₂^- • )

By formula: C₆H₄ClNO₂^- + C₂H₆OS = (C₆H₄ClNO₂^- • C₂H₆OS)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + C₂H₆OS = (C₆H₄N₂O₄^- • C₂H₆OS)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + C₂H₆OS = (C₆H₄N₂O₄^- • C₂H₆OS)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + C₂H₆OS = (C₆H₄N₂O₄^- • C₂H₆OS)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₂H₆OS = (C₇H₇NO₂^- • C₂H₆OS)

Free energy of reaction

C₆F₄O₂^- +  = (C₆F₄O₂^- • )

By formula: C₆F₄O₂^- + C₂H₆OS = (C₆F₄O₂^- • C₂H₆OS)

Free energy of reaction

 +  = ( • )

By formula: C₆H₄O₂^- + C₂H₆OS = (C₆H₄O₂^- • C₂H₆OS)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₂H₆OS = (C₇H₄N₂O₂^- • C₂H₆OS)

Free energy of reaction

 +  = ( • )

By formula: K⁺ + C₂H₆OS = (K⁺ • C₂H₆OS)

C₄H₂O₃^- +  = (C₄H₂O₃^- • )

By formula: C₄H₂O₃^- + C₂H₆OS = (C₄H₂O₃^- • C₂H₆OS)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₂H₆OS = (C₇H₄N₂O₂^- • C₂H₆OS)

Free energy of reaction

2 +  = 2

By formula: 2C₂H₆S + O₂ = 2C₂H₆OS

=  + 0.5

By formula: C₂H₆O₂S = C₂H₆OS + 0.5O₂

( • 2) +  = ( • 3)

By formula: (Cl^- • 2C₂H₆OS) + C₂H₆OS = (Cl^- • 3C₂H₆OS)

( • 3) +  = ( • 4)

By formula: (Cl^- • 3C₂H₆OS) + C₂H₆OS = (Cl^- • 4C₂H₆OS)

( • 4) +  = ( • 5)

By formula: (Cl^- • 4C₂H₆OS) + C₂H₆OS = (Cl^- • 5C₂H₆OS)

( • 2) +  = ( • 3)

By formula: (I^- • 2C₂H₆OS) + C₂H₆OS = (I^- • 3C₂H₆OS)

( • 2) +  = ( • 3)

By formula: (Br^- • 2C₂H₆OS) + C₂H₆OS = (Br^- • 3C₂H₆OS)

( • ) +  = ( • 2)

By formula: (Cl^- • C₂H₆OS) + C₂H₆OS = (Cl^- • 2C₂H₆OS)

( • ) +  = ( • 2)

By formula: (I^- • C₂H₆OS) + C₂H₆OS = (I^- • 2C₂H₆OS)

( • ) +  = ( • 2)

By formula: (Br^- • C₂H₆OS) + C₂H₆OS = (Br^- • 2C₂H₆OS)

 +  = ( • )

By formula: Na⁺ + C₂H₆OS = (Na⁺ • C₂H₆OS)

Free energy of reaction

( • 2) +  = ( • 3)

By formula: (K⁺ • 2C₂H₆OS) + C₂H₆OS = (K⁺ • 3C₂H₆OS)

( • 3) +  = ( • 4)

By formula: (K⁺ • 3C₂H₆OS) + C₂H₆OS = (K⁺ • 4C₂H₆OS)

( • ) +  = ( • 2)

By formula: (K⁺ • C₂H₆OS) + C₂H₆OS = (K⁺ • 2C₂H₆OS)

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₂H₆OS = (C₇H₄N₂O₂^- • C₂H₆OS)

C₆H₄NO₃^- +  = (C₆H₄NO₃^- • )

By formula: C₆H₄NO₃^- + C₂H₆OS = (C₆H₄NO₃^- • C₂H₆OS)

C₆H₄NO₃^- +  = (C₆H₄NO₃^- • )

By formula: C₆H₄NO₃^- + C₂H₆OS = (C₆H₄NO₃^- • C₂H₆OS)

 +  = C₁₂H₁₂O₃S^-

By formula: C₁₀H₆O₂^- + C₂H₆OS = C₁₂H₁₂O₃S^-

F₆S^- +  = (F₆S^- • )

By formula: F₆S^- + C₂H₆OS = (F₆S^- • C₂H₆OS)

Free energy of reaction

 +  = ( • )

By formula: C₇F₁₄^- + C₂H₆OS = (C₇F₁₄^- • C₂H₆OS)

Free energy of reaction

 +  = ( • )

By formula: C₁₀H₆O₂^- + C₂H₆OS = (C₁₀H₆O₂^- • C₂H₆OS)

Free energy of reaction

Henry's Law 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 by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, 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]

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]

Sieck, 1985
Sieck, L.W., Thermochemistry of Solvation of NO₂^- and C₆H₅NO₂^- by Polar Molecules in the Vapor Phase. Comparison with Cl^- and Variation with Ligand Structure., J. Phys. Chem., 1985, 89, 25, 5552, https://doi.org/10.1021/j100271a049 . [all data]

Chowdhury, Grimsrud, et al., 1987
Chowdhury, S.; Grimsrud, E.P.; Kebarle, P., Bonding of Charged Delocalized Anions to Protic and Dipolar Aprotic Solvent Molecules, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Chowdhury, 1987
Chowdhury, S. Grimsrud, Bonding of Charge Delocalized Anions to Protic and Dipolar Aprotic Solvents, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Magnera, Caldwell, et al., 1984
Magnera, T.F.; Caldwell, G.; Sumner, J.; Ikuta, S.; Kebarle, P., Solvation of the halide anions in dimethyl sulfoxide. Factors involved in enhanced reactivity of negative ions in dipolar aprotic solvents, J. Am. Chem. Soc., 1984, 106, 6140. [all data]

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]

Lau, Saluja, et al., 1980
Lau, Y.K.; Saluja, P.P.S.; Kebarle, P., The Proton in Dimethyl Sulfoxide and Acetone. Results from Gas - Phase Ion Equilibria Involving (Me2SO)nH+ and (Me2CO)nH+, J. Am. Chem. Soc., 1980, 102, 25, 7429, https://doi.org/10.1021/ja00545a004 . [all data]

Sunner, 1984
Sunner, J. Kebarle, Ion - Solvent Molecule Interactions in the Gas Phase. The Potassium Ion and Me2SO, DMA, DMF, and Acetone, J. Am. Chem. Soc., 1984, 106, 21, 6135, https://doi.org/10.1021/ja00333a002 . [all data]

Klassen, Anderson, et al., 1996
Klassen, J.S.; Anderson, S.G.; Blades, A.T.; Kebarle, P., Reaction Enthalpies for M+L = M+ + L, Where M+ = Na+ and K+ and L = Acetamide, N-Methylacetamide, N,N-Dimethylacetamide, Glycine, and Glycylglycine, from Determinations of the Collision-Induced Dissociation Thresholds, J. Phys. Chem., 1996, 100, 33, 14218, https://doi.org/10.1021/jp9608382 . [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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Knighton, Zook, et al., 1990
Knighton, W.B.; Zook, D.R.; Grimsrud, E.P., Cluster-Assisted Decomposition Reactions of the Molecular Anions of SF6 and C7F14, J. Am. Soc. Mass Spectrom., 1990, 1, 5, 372, https://doi.org/10.1016/1044-0305(90)85017-G . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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