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

Go To: Top, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), 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

Ion clustering data

Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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:
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

IR Spectrum

Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• LIQUID (NEAT); PERKIN-ELMER 180; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 4000-1330 CM^-1, 10% IN CS2 FOR 1330-600 CM^-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION (10.75% IN CCl4 FOR 3800-1300, 2.24% IN CS2 FOR 1300-620, AND 10.75% IN CCl4 FOR 620-250 CM^-1) VERSUS SOLVENT; Not specified, most likely a grating or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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 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, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

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

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]

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

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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]

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

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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]

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]

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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, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  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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