Dimethyl Sulfoxide
- Formula: C2H6OS
- Molecular weight: 78.133
- IUPAC Standard InChIKey: IAZDPXIOMUYVGZ-UHFFFAOYSA-N
- 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:
- 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
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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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -48.61 ± 0.33 | kcal/mol | Ccr | Masuda, Nagano, et al., 1994 | H2SO4 (1:115 H2O); ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -486.93 ± 0.30 | kcal/mol | Ccr | Masuda, Nagano, et al., 1994 | H2SO4 (1:115 H2O); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 45.120 | cal/mol*K | N/A | Clever and Westrum, 1970 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
35.705 | 298.15 | Grolier, Roux-Desgranges, et al., 1993 | DH |
35.440 | 298.15 | Barta, Kooner, et al., 1989 | DH |
36.71 | 298.15 | Rodante and Marrosu, 1988 | DH |
36.62 | 298.15 | Lankford and Criss, 1987 | DH |
37.26 | 298.15 | de Visser and Somsen, 1979 | DH |
37.26 | 298.15 | De Visser, Heuvelsland, et al., 1978 | DH |
36.611 | 298.15 | Clever and Westrum, 1970 | T = 5 to 350 K.; DH |
35.61 | 298.15 | Kenttmaa and Lindberg, 1960 | T = 298, 343 K.; DH |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 463. ± 1. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 291.65 | K | N/A | Lindberg and Stenholm, 1966 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 291.57 | K | N/A | Douglas, 1948 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 291.65 | K | N/A | Douglas, 1946 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 291.59 | K | N/A | Clever and Westrum, 1970, 2 | Uncertainty assigned by TRC = 0.1 K; TRC |
Ttriple | 291.67 | K | N/A | Clever and Westrum, 1970, 2 | Uncertainty assigned by TRC = 0.06 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12.6 ± 0.1 | kcal/mol | V | Douglas, 1948, 2 | ALS |
ΔvapH° | 12.6 ± 0.1 | kcal/mol | RG | Douglas, 1948, 3 | Based on data from 293. to 323. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.5 | 368. | TGA | Al-Najjar and Al-Sammerrai, 2007 | Based on data from 353. to 383. K.; AC |
11.6 | 392. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 377. to 483. K.; AC |
12.4 | 320. | A | Stephenson and Malanowski, 1987 | Based on data from 305. to 464. K.; AC |
12.5 | 308. | N/A | Sassa, Konishi, et al., 1974 | Based on data from 298. to 318. K.; AC |
12.1 | 340. | MM | Jakli and Alexander Van Hook, 1972 | Based on data from 325. to 442. K. See also Boublik, Fried, et al., 1984.; AC |
12.5 | 318. | N/A | NISHIMURA, NAKAYAMA, et al., 1972 | Based on data from 303. to 423. K.; AC |
12.5 | 308. | N/A | Meszaros, 1969 | Based on data from 293. to 323. K.; AC |
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.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
325.49 to 442.09 | 4.48536 | 1807.002 | -60.995 | Jakli and van Hook, 1972 | Coefficents calculated by NIST from author's data. |
293. to 323. | 5.22468 | 2239.161 | -29.215 | Douglas, 1948, 3 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.4340 | 291.67 | Clever and Westrum, 1970 | DH |
3.435 | 291.7 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.77 | 291.67 | Clever and Westrum, 1970 | DH |
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 211.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 204.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.013921 ± 0.000087 | N/A | Hammer, Diri, et al., 2003 | B |
0.007416 | EFD | Suess, Liu, et al., 2003 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.10 | PE | Kimura, Katsumata, et al., 1981 | LLK |
9.08 ± 0.09 | EI | Potzinger, Stracke, et al., 1975 | LLK |
9.20 ± 0.05 | EI | Distefano, Foffani, et al., 1971 | LLK |
9.20 | EI | Distefano, Foffani, et al., 1971, 2 | LLK |
9.9 ± 0.1 | EI | Blais, Cottin, et al., 1970 | RDSH |
9.10 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
9.01 | PE | Bock and Solouki, 1974 | Vertical value; LLK |
9.11 | PE | Mines, Thomas, et al., 1972 | Vertical value; LLK |
9.01 | PE | Bock and Solouki, 1972 | Vertical value; LLK |
Appearance energy determinations
De-protonation reactions
C2H5OS- + =
By formula: C2H5OS- + H+ = C2H6OS
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 373.5 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 374.3 ± 2.3 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 366.4 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 367.2 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
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
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118614 |
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,
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Dimethylsulfoxide and dimethylsulfone. Heat capacities, enthalpies of fusion, and thermodynamic properties,
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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,
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Partial molar heat caqpacities of selected electrolytes and benzene in methanol and dimethyldulfoxide at 25, 40 and 80°C,
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Volumes and heats of mixing of dimethyl sulfoxide-water solutions,
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Viscosities, Densities, and Related Properties of Binary Mixtures Containing Dimethyl Sulphoxide and Mono-Subst. Benzenes or Guaiacol,
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Vapor Pressure of Methyl Sulfoxide from 20 to 50 deg. Calculation of the Heat of Vaporization,
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Douglas, Thomas B.,
Vapor Pressure of Methyl Sulfoxide from 20 to 50°. Calculation of the Heat of Vaporization,
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Thermogravimetric determination of the heat of vaporization of some highly polar solvents,
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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
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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,
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Jakli, Gyorgy; Alexander Van Hook, W.,
The vapor pressures of dimethyl sulfoxide and hexadeuterodimethyl sulfoxide from about 313 to 453 K,
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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]
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VAPOR PRESSURE OF PURE DMSO AND VAPOR-LIQUID EQUILIBRIA IN DMSO-H2O SYSTEM UNDER ISOBARIC CONDITIONS,
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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,
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Domalski and Hearing, 1996
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Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
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Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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Dipole-bound negative ions: Collisional destruction and blackbody-radiation-induced photodetachment,
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Ionisierungs- und Auftrittspotentialmessungen an Dialkylsulfoxiden,
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Ionisation positive et negative dans le dimethylsulfoxyde en phase gazeuse,
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Photoelektronenspektren und molekuleigenschaften, XXXV. Sulfoxide X2SO - beispiele fur den nutzen von korrelations - diagrammen bei der diskussion von substituenteneffekten und von geometrischen storungen,
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The sulfoxide bond,
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Unimolecular dissociation of energy-selected dimethyl sulfoxide,
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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,
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Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
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Cumming and Kebarle, 1978
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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),
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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
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