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, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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 | -83.5 ± 2.3 | kJ/mol | Ccb | Voronkov, Klyuchnikov, et al., 1989 | |
ΔfH°gas | -82.72 ± 0.79 | kJ/mol | Ccr | Hubbard, Good, et al., 1958 | see Hubbard, Katz, et al., 1954 |
Condensed phase thermochemistry data
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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 | -119.3 ± 2.0 | kJ/mol | Ccb | Voronkov, Klyuchnikov, et al., 1989 | ALS |
ΔfH°liquid | -119.4 ± 0.84 | kJ/mol | Ccr | Hubbard, Good, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -118.6 ± 0.79 kJ/mol; see Hubbard, Katz, et al., 1954; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3486.1 ± 0.67 | kJ/mol | Ccr | Hubbard, Good, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -3485.4 ± 0.67 kJ/mol; see Hubbard, Katz, et al., 1954; ALS |
ΔcH°liquid | -3471. | kJ/mol | Ccb | Berthelot, 1901 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 269.28 | J/mol*K | N/A | Scott, Finke, et al., 1952 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
171.42 | 298.15 | Scott, Finke, et al., 1952 | T = 16 to 316 K.; DH |
Phase change data
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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.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 365. ± 1. | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 169.85 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 169.24 | K | N/A | Mcallan, Cullum, et al., 1951 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 169.85 | K | N/A | Timmermans and Hennaut-Roland, 1935 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 169.21 | K | N/A | Scott, Finke, et al., 1952, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 557. | K | N/A | Majer and Svoboda, 1985 | |
Tc | 557.0 | K | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.5 K; by disappearance of meniscus; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 39.60 | bar | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.4053 bar; vapor pressure at Tc; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.151 | mol/l | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.02 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 35.9 ± 0.6 | kJ/mol | AVG | N/A | Average of 8 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
31.77 | 365.3 | N/A | Majer and Svoboda, 1985 | |
34.9 | 327. | N/A | Baev, 2008 | Based on data from 293. to 361. K.; AC |
34.4 | 333. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 318. to 396. K. See also Scott, Finke, et al., 1952 and Osborn and Douslin, 1966.; AC |
34.8 | 324. | EB | White, Barnard--Smith, et al., 1952 | Based on data from 309. to 371. K.; AC |
37.5 | 248. | N/A | Stull, 1947 | Based on data from 233. to 361. K.; AC |
33.5 | 364. | N/A | Thompson and Linnett, 1935 | AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
325. to 365. | 51.83 | 0.2843 | 557. | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
319.07 to 395.58 | 4.05326 | 1257.833 | -54.488 | Osborn and Douslin, 1966 | |
233.6 to 361. | 4.66583 | 1560.523 | -26.557 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
361. to 536. | 4.41669 | 1541.596 | -11.154 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.903 | 169.21 | Scott, Finke, et al., 1952 | DH |
11.92 | 169.2 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
70.35 | 169.21 | Scott, Finke, et al., 1952 | DH |
Reaction thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
By formula: C4H10S+ + C4H10S = (C4H10S+ • C4H10S)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 104. | kJ/mol | DT | James, McKee, et al., 1996 | gas phase; ΔrH(0K) = 107. kJ/mol |
ΔrH° | 112. | kJ/mol | DT | Deng, Illies, et al., 1995 | gas phase; ΔrH(0K) = 120. kJ/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 118. | J/mol*K | DT | James, McKee, et al., 1996 | gas phase; ΔrH(0K) = 107. kJ/mol |
ΔrS° | 143. | J/mol*K | DT | Deng, Illies, et al., 1995 | gas phase; ΔrH(0K) = 120. kJ/mol |
Henry's Law data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
0.56 | 4600. | M | N/A |
0.46 | V | N/A |
IR Spectrum
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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
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 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 |
State | gas |
Instrument | HP-GC/MS/IRD |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, UV/Visible spectrum, 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
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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 | Japan AIST/NIMC Database- Spectrum MS-NW-2557 |
NIST MS number | 229882 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | Fehnel and Carmack, 1949 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 3281 |
Instrument | Beckman DU |
Melting point | -103.9 |
Boiling point | 92.1 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
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,
J. Am. Chem. Soc., 1951, 73, 3627-32. [all data]
Timmermans and Hennaut-Roland, 1935
Timmermans, J.; Hennaut-Roland, M.,
Physical constants of 20 organic compounds. VII.,
J. Chim. Phys. Phys.-Chim. Biol., 1935, 32, 501. [all data]
Scott, Finke, et al., 1952, 2
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, 4656-62. [all data]
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
Berthoud, A.; Brum, R.,
Physical Properties of Some Organic Compounds.,
J. Chim. Phys. Phys.-Chim. Biol., 1924, 21, 143-60. [all data]
Baev, 2008
Baev, A.K.,
The thermodynamic characteristics of diethylzinc-diethylsulfur solutions,
Russ. J. Phys. Chem. A, 2008, 82, 8, 1266-1272, https://doi.org/10.1134/S0036024408080050
. [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
. [all data]
Osborn and Douslin, 1966
Osborn, A.G.; Douslin, D.R.,
Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum.,
J. Chem. Eng. Data, 1966, 11, 4, 502-509, https://doi.org/10.1021/je60031a014
. [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
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Thompson and Linnett, 1935
Thompson, H.W.; Linnett, J.W.,
The vapour pressures of some alkyl sulphides,
Trans. Faraday Soc., 1935, 31, 1743, https://doi.org/10.1039/tf9353101743
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
James, McKee, et al., 1996
James, M.A.; McKee, M.L.; Illies, A.J.,
Gas-phase bond strength and atomic connectivity studies of the unsymmetrical two-center three-electron ion, [Et2S...SMe2]+,
J. Am. Chem. Soc., 1996, 118, 33, 7836, https://doi.org/10.1021/ja960455h
. [all data]
Deng, Illies, et al., 1995
Deng, Y.; Illies, A.J.; James, M.A.; McKee, M.L.; Peschke, M.,
A Definitive Investigation of the Gas-Phase Two-Center Three-electron Bond in [H2S:SH2+], [Me2S:SMe2]+, and [Et2S:SEt2]+: Therory and Experiment,
J. Am. Chem. Soc., 1995, 117, 1, 420, https://doi.org/10.1021/ja00106a048
. [all data]
Fehnel and Carmack, 1949
Fehnel, E.A.; Carmack, M.,
The ultraviolet absorption spectra of organic sulfur compounds. I. Compounds containing the sulfide function,
J. Am. Chem. Soc., 1949, 71, 84-93. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy 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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