Dimethyl sulfide
- Formula: C2H6S
- Molecular weight: 62.134
- IUPAC Standard InChIKey: QMMFVYPAHWMCMS-UHFFFAOYSA-N
- CAS Registry Number: 75-18-3
- 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: Methane, thiobis-; Methyl sulfide; Dimethyl monosulfide; Dimethyl thioether; DMS; Methyl monosulfide; 2-Thiapropane; Dimethyl sulphide; Thiobismethane; (CH3)2S; Dimethylsulfid; Exact-S; Methyl sulphide; Methylthiomethane; Sulfure de methyle; 2-Thiopropane; UN 1164; Methyl thioether; Sulfide, methyl-; Methane, 1,1'-thiobis-; (Methylsulfanyl)methane
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Gas phase thermochemistry data
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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -8.96 ± 0.48 | kcal/mol | Ccb | Voronkov, Klyuchnikov, et al., 1989 | ALS |
ΔfH°gas | -8.98 ± 0.14 | kcal/mol | Ccr | McCullough, Hubbard, et al., 1957 | ALS |
ΔfH°gas | -7.74 | kcal/mol | N/A | Douglas, 1946 | Value computed using ΔfHliquid° value of -60.2 kj/mol from Douglas, 1946 and ΔvapH° value of 27.8 kj/mol from McCullough, Hubbard, et al., 1957.; DRB |
Phase change data
Go To: Top, Gas phase thermochemistry 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 311. ± 3. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 174.88 | K | N/A | Haines, Helm, et al., 1956 | Uncertainty assigned by TRC = 0.06 K; TRC |
Tfus | 174.90 | K | N/A | Mcallan, Cullum, et al., 1951 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 174.85 | K | N/A | Osborne, Doescher, et al., 1942 | Uncertainty assigned by TRC = 0.03 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 503. | K | N/A | Majer and Svoboda, 1985 | |
Tc | 503.0 | K | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.4 K; by disappearance of meniscus; TRC |
Tc | 503.0 | K | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.4 K; by apperanance of turbidity; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 54.58 | atm | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.4000 atm; vapor pressure at Tc; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 4.972 | mol/l | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
ρc | 4.84 | mol/l | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 6.65 ± 0.07 | kcal/mol | AVG | N/A | Average of 8 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.5 | 310.5 | N/A | Majer and Svoboda, 1985 | |
6.91 | 283. | A | Stephenson and Malanowski, 1987 | Based on data from 268. to 319. K.; AC |
6.62 | 322. | A | Stephenson and Malanowski, 1987 | Based on data from 307. to 379. K.; AC |
6.36 | 387. | A | Stephenson and Malanowski, 1987 | Based on data from 372. to 453. K.; AC |
6.38 | 462. | A | Stephenson and Malanowski, 1987 | Based on data from 447. to 503. K.; AC |
6.88 ± 0.02 | 276. | C | McCullough, Hubbard, et al., 1957 | AC |
6.67 ± 0.02 | 292. | C | McCullough, Hubbard, et al., 1957 | AC |
6.45 ± 0.02 | 310. | C | McCullough, Hubbard, et al., 1957 | AC |
6.74 | 302. | EB | White, Barnard--Smith, et al., 1952 | Based on data from 287. to 318. K.; AC |
6.91 | 278. | N/A | Osborne, Doescher, et al., 1942, 2 | Based on data from 251. to 293. K.; AC |
6.91 | 310. | N/A | Thompson and Linnett, 1935 | AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
276. to 311. | 9.928 | 0.2731 | 503. | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
250.60 to 293.24 | 4.28142 | 1201.134 | -29.906 | Osborne, Doescher, et al., 1942, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.91 | 174.9 | Domalski and Hearing, 1996 | AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, 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
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C2H6S+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.69 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 198.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 191.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
Appearance energy determinations
De-protonation reactions
C2H5S- + =
By formula: C2H5S- + H+ = C2H6S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 390.2 ± 1.5 | kcal/mol | D-EA | Moran and Ellison, 1988 | gas phase; B |
ΔrH° | 393.2 ± 2.1 | kcal/mol | G+TS | Ingemann and Nibbering, 1985 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 383.0 ± 1.7 | kcal/mol | H-TS | Moran and Ellison, 1988 | gas phase; B |
ΔrG° | 386.0 ± 2.0 | kcal/mol | IMRE | Ingemann and Nibbering, 1985 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Voronkov, Klyuchnikov, et al., 1989
Voronkov, M.G.; Klyuchnikov, V.A.; Kolabin, S.N.; Shvets, G.N.; Varusin, P.I.; Deryagina, E.N.; Korchevin, N.A.; Tsvetnitskaya, S.I.,
Thermochemical properties of diorganyl chalcogenides and dichalcogenides RMnR(M = S, Se, Te; n = 1, 2).,
Dokl. Phys. Chem. (Engl. Transl.), 1989, 307, 650-653, In original 1139. [all data]
McCullough, Hubbard, et al., 1957
McCullough, J.P.; Hubbard, W.N.; Frow, F.R.; Hossenlopp, I.A.; Waddington, G.,
Ethanethiol and 2-thiapropane: Heats of formation and isomerization; the chemical thermodynamic properties from 0 to 1000°K,
J. Am. Chem. Soc., 1957, 79, 561-566. [all data]
Douglas, 1946
Douglas, T.B.,
Heats of formation of liquid methyl sulfoxide and crystalline methyl sulfone at 18°,
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Haines, Helm, et al., 1956
Haines, W.E.; Helm, R.V.; Cook, G.L.; Ball, J.S.,
Purification and Properties of Organic Sulfur Compounds,
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Mcallan, Cullum, et al., 1951
Mcallan, D.T.; Cullum, T.V.; Dean, R.A.; Fidler, F.A.,
The Preparation and Properties of Sulfur Compounds Related to Petroleum I. The Dialkyl Sulfides and Disulfides,
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Osborne, Doescher, et al., 1942
Osborne, D.W.; Doescher, R.N.; Yost, D.M.,
The heat capacity, heats of fusion and vaporization, vapor pressure and entropy of dimethyl sulfide.,
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Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Berthoud and Brum, 1924
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Physical Properties of Some Organic Compounds.,
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Herz and Neukirch, 1923
Herz, W.; Neukirch, E.,
On Knowldge of the Critical State,
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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
. [all data]
White, Barnard--Smith, et al., 1952
White, P.T.; Barnard--Smith, D.G.; Fidler, F.A.,
Vapor Pressure--Temperature Relationships of Sulfur Compounds Related to Petroleum,
Ind. Eng. Chem., 1952, 44, 6, 1430-1438, https://doi.org/10.1021/ie50510a064
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Osborne, Doescher, et al., 1942, 2
Osborne, D.W.; Doescher, R.N.; Yost, D.M.,
The heat capacity, heats of fusion and vaporization, vapor pressure and entropy of dimethyl sulfide,
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Thompson and Linnett, 1935
Thompson, H.W.; Linnett, J.W.,
The vapour pressures of some alkyl sulphides,
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Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
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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]
Carnovale, Livett, et al., 1983
Carnovale, F.; Livett, M.K.; Peel, J.B.,
Identification of the gas phase trimer (CH3)2S.(HF)2 by photoelectron spectroscopy,
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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
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Aue, Webb, et al., 1980
Aue, D.H.; Webb, H.M.; Davidson, W.R.; Vidal, M.; Bowers, M.T.; Goldwhite, H.; Vertal, L.E.; Douglas, J.E.; Kollman, P.A.; Kenyon, G.L.,
Proton affinities photoelectron spectra of three-membered-ring J. Heterocycl. Chem.,
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Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T.,
Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements
in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]
McDiarmid, 1974
McDiarmid, R.,
Assignments of Rydberg and valence transitions in the electronic absorption spectrum of dimethyl sulfide,
J. Chem. Phys., 1974, 61, 274. [all data]
Scott, Causley, et al., 1973
Scott, J.D.; Causley, G.C.; Russell, B.R.,
Vacuum ultraviolet absorption spectra of dimethylsulfide, dimethylselenide, and dimethyltelluride,
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Mollere, Bock, et al., 1973
Mollere, P.; Bock, H.; Becker, G.; Fritz, G.,
Photoelectron spectra and molecular properties. XXI. Dimethyl sulfide, methyl silyl sulfide, and disilyl sulfide,
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Bunzli, Frost, et al., 1973
Bunzli, J.C.; Frost, D.C.; Weiler, L.,
Photoelectron spectrum of 7-thiabicyclo[2.2.1]heptane,
J. Am. Chem. Soc., 1973, 95, 7880. [all data]
Schafer and Schweig, 1972
Schafer, W.; Schweig, A.,
Evidence against the significance of C-S hyperconjugation in determining the conformation of allyl methyl sulphide,
J. Chem. Soc., Chem. Commun., 1972, 824. [all data]
Akopyan, Sergeev, et al., 1970
Akopyan, M.E.; Sergeev, Yu.L.; Vilesov, F.I.,
Photionization in vapors of aliphatic sulfides. I. Methymercaptan, dimethyl and diethyl sulfides,
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Cullen, Frost, et al., 1969
Cullen, W.R.; Frost, D.C.; Vroom, D.A.,
Ionization potentials of some sulfur compounds,
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Keyes and Harrson, 1968
Keyes, B.G.; Harrson, A.G.,
The fragmentation of aliphatic sulfur compounds by electron impact,
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Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
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Chang, Young, et al., 1986
Chang, F.C.; Young, V.Y.; Prather, J.W.; Cheng, K.L.,
Study of methyl chalcogen compounds with ultraviolet photoelectron spectroscopy,
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Kobayashi, 1978
Kobayashi, T.,
A new rule for photoelectron angular distributions of molecules,
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Kobayashi, 1978, 2
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A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes,
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Wagner and Bock, 1974
Wagner, G.; Bock, H.,
Photoelektronenspektren und molekuleigenschaften, XXVI. Die delokalisation von schwefel-elektronenpaaren in alkylsulfiden und -disulfiden,
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Schweig and Thiel, 1974
Schweig, A.; Thiel, W.,
Photoionization cross sections: He I- and He II-photoelectron spectra of homologous oxygen and sulphur compounds,
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Frost, Herring, et al., 1972
Frost, D.C.; Herring, F.G.; Katrib, A.; McDowell, C.A.; McLean, R.A.N.,
Photoelectron spectra of CH3SH, (CH3)2S, C6H5SH, and C6H5CH2SH; the bonding between sulfur and carbon,
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Cradock and Whiteford, 1972
Cradock, S.; Whiteford, R.A.,
Photoelectron spectra of the methyl, silyl and germyl derivatives of the group VI elements,
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Ermolenko, Akopyan, et al., 1983
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Decomposition of dimethyl sulfide molecular ions. Randomization of states during photoionization dissociation of molecules,
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Mass spectra, appearance potentials, heats of formation, and bond energies of some alkyl and perfluoroalkyl sulfides,
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Electron impact studies of some sulphides and disulphides,
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Stabilization energies of substituted methyl cations. The effect of strong demand on the resonance order,
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Moran and Ellison, 1988
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Photoelectron Spectroscopy of Sulfur Ions,
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Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy 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 ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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