Diethyl sulfide
- Formula: C4H10S
- Molecular weight: 90.187
- IUPAC Standard InChIKey: LJSQFQKUNVCTIA-UHFFFAOYSA-N
- CAS Registry Number: 352-93-2
- 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. - Other names: Ethane, 1,1'-thiobis-; Ethyl sulfide; Diethyl thioether; Ethyl monosulfide; Ethyl thioether; Ethylthioethane; Thioethyl ether; 3-Thiapentane; 1,1'-Thiobisethane; Diethyl sulphide; (C2H5)2S; Diethylsulfid; Sulfodor; UN 2375; NSC 75157
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Gas phase thermochemistry data
Go To: Top, Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -20.0 ± 0.55 | kcal/mol | Ccb | Voronkov, Klyuchnikov, et al., 1989 | |
ΔfH°gas | -19.77 ± 0.19 | kcal/mol | Ccr | Hubbard, Good, et al., 1958 | see Hubbard, Katz, et al., 1954 |
Condensed phase thermochemistry 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:
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 | -28.51 ± 0.48 | kcal/mol | Ccb | Voronkov, Klyuchnikov, et al., 1989 | ALS |
ΔfH°liquid | -28.54 ± 0.20 | kcal/mol | Ccr | Hubbard, Good, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -28.34 ± 0.19 kcal/mol; see Hubbard, Katz, et al., 1954; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -833.20 ± 0.16 | kcal/mol | Ccr | Hubbard, Good, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -833.04 ± 0.16 kcal/mol; see Hubbard, Katz, et al., 1954; ALS |
ΔcH°liquid | -829.6 | kcal/mol | Ccb | Berthelot, 1901 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 64.359 | cal/mol*K | N/A | Scott, Finke, et al., 1952 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
40.970 | 298.15 | Scott, Finke, et al., 1952 | T = 16 to 316 K.; DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.42 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 204.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 197.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.41 | CTS | Aloisi, Santini, et al., 1974 | LLK |
8.42 ± 0.01 | PI | Akopyan, Sergeev, et al., 1970 | RDSH |
8.430 ± 0.005 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.4 | PE | Aue and Bowers, 1979 | Vertical value; LLK |
8.46 | PE | Weiner and Lattman, 1978 | Vertical value; LLK |
8.44 | PE | Wagner and Bock, 1974 | Vertical value; LLK |
8.44 | PE | Bock, Wagner, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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]
Hubbard, Good, et al., 1958
Hubbard, W.N.; Good, W.D.; Waddington, G.,
The heats of combustion, formation and isomerization of the seven isomeric C4H10S alkane thiols and sulfides,
J. Phys. Chem., 1958, 62, 614-617. [all data]
Hubbard, Katz, et al., 1954
Hubbard, W.N.; Katz, C.; Waddington, G.,
A rotating combustion bomb for precision calorimetry. Heats of combustion of some sulfur-containing compounds,
J. Phys. Chem., 1954, 58, 142. [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]
Berthelot, 1901
Berthelot, M.,
Chimie Organique. - Nouvelles recherches sur l'isomerie des ethers sulfocyaniques,
Compt. Rend., 1901, 132, 57-58. [all data]
Scott, Finke, et al., 1952
Scott, D.W.; Finke, H.L.; Hubbard, W.N.; McCullough, J.P.; Oliver, G.D.; Gross, M.E.; Katz, C.; Williamson, K.D.; Waddington, G.; Huffman, H.M.,
3-Thiapentane: heat capacity, heats of fusion and vaporization, vapor pressure, entropy, heat of formation and thermodynamic functions,
J. Am. Chem. Soc., 1952, 74, 4656-4662. [all data]
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]
Aloisi, Santini, et al., 1974
Aloisi, G.G.; Santini, S.; Sorriso, S.,
Molecular complexes of substituted diphenyl sulphides with π acceptors. Charge transfer spectra and ionization potentials of the donors,
J. Chem. Soc. Faraday Trans. 1, 1974, 70, 1908. [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,
High Energy Chem., 1970, 4, 265, In original 305. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
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]
Weiner and Lattman, 1978
Weiner, M.A.; Lattman, M.,
Ultraviolet photoelectron spectra of some Cr(CO)5L complexes containing organosulfide and organophosphine ligands,
Inorg. Chem., 1978, 17, 1084. [all data]
Wagner and Bock, 1974
Wagner, G.; Bock, H.,
Photoelektronenspektren und molekuleigenschaften, XXVI. Die delokalisation von schwefel-elektronenpaaren in alkylsulfiden und -disulfiden,
Chem. Ber., 1974, 107, 68. [all data]
Bock, Wagner, et al., 1972
Bock, H.; Wagner, G.; Kroner, J.,
Photoelektronenspektren und molekuleigenschaften, XIV. Die delokalisation des schwefel-elektronenpaar in CH3S-substituierten aromaten,
Chem. Ber., 1972, 105, 3850. [all data]
Hobrock and Kiser, 1963
Hobrock, B.G.; Kiser, R.W.,
Electron impact investigations of sulfur compounds. III. 2-Thiapropane, 3-thiapentane, and 2,3,4-trithiapentane,
J. Phys. Chem., 1963, 67, 1283. [all data]
Keyes and Harrson, 1968
Keyes, B.G.; Harrson, A.G.,
The fragmentation of aliphatic sulfur compounds by electron impact,
J. Am. Chem. Soc., 1968, 90, 5671. [all data]
Gal'perin, Bogolyubov, et al., 1969
Gal'perin, Ya.V.; Bogolyubov, G.M.; Grishin, N.N.; Petrov, A.A.,
Organic derivatives of elements of groups V and VI. VI. Mass spectra of compounds with S-S bonds,
Zh. Obshch. Khim., 1969, 39, 1599, In original 1567. [all data]
Gowenlock, Kay, et al., 1963
Gowenlock, B.G.; Kay, J.; Majer, J.R.,
Electron impact studies of some sulphides and disulphides,
J. Chem. Soc. Faraday Trans., 1963, 59, 2463. [all data]
Broer and Weringa, 1980
Broer, W.J.; Weringa, W.D.,
Potential energy profiles for the unimolecular reactions of [C3H7S]+ ions,
Org. Mass Spectrom., 1980, 15, 229. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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