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

Go To: Top, 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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

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

( • ) +  = ( • 2)

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

( • 2) +  = ( • 3)

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

C₂H₇OS⁺ +  = (C₂H₇OS⁺ • )

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

(C₂H₇OS⁺ • ) +  = (C₂H₇OS⁺ • 2)

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

C₄H₂O₃^- +  = (C₄H₂O₃^- • )

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

Free energy of reaction

C₆F₄O₂^- +  = (C₆F₄O₂^- • )

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

C₆H₄ClNO₂^- +  = (C₆H₄ClNO₂^- • )

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

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

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

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

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

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

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

Free energy of reaction

C₆H₄NO₃^- +  = (C₆H₄NO₃^- • )

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

C₆H₄NO₃^- +  = (C₆H₄NO₃^- • )

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

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

 +  = ( • )

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

Free energy of reaction

C₆H₅NO₂^- +  = (C₆H₅NO₂^- • )

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

 +  = ( • )

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

Free energy of reaction

C₇H₄F₃NO₂^- +  = (C₇H₄F₃NO₂^- • )

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

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

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

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

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

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

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

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

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

Free energy of reaction

C₇H₇NO₃^- +  = (C₇H₇NO₃^- • )

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

 +  = ( • )

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

Free energy of reaction

 +  = C₁₂H₁₂O₃S^-

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

( • 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)

F₆S^- +  = (F₆S^- • )

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

Free energy of reaction

 +  = ( • )

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

( • ) +  = ( • 2)

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

( • 2) +  = ( • 3)

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

( • 2) +  = ( • 3)

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

( • 3) +  = ( • 4)

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

( • 4) +  = ( • 5)

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

( • 5) +  = ( • 6)

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

 +  = ( • )

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

Free energy of reaction

 +  = ( • )

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

Free energy of reaction

References

Go To: Top, Ion clustering data, Notes

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

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]

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]

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]

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]

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]

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]

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]

Notes

Go To: Top, Ion clustering data, References

• Symbols used in this document:
  

  T	Temperature
  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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