Diethyl disulfide
- Formula: C4H10S2
- Molecular weight: 122.252
- IUPAC Standard InChIKey: CETBSQOFQKLHHZ-UHFFFAOYSA-N
- CAS Registry Number: 110-81-6
- 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: Disulfide, diethyl; Ethyl disulfide; Ethyldithioethane; 3,4-Dithiahexane; Diethyl disulphide; (C2H5S)2; Diethyldisulfid; Ethyl disulphide; NSC 8839; 1-(Ethyldisulfanyl)ethane
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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 | -120.0 ± 3.0 | kJ/mol | Ccb | Voronkov, Klyuchnikov, et al., 1989 | ALS |
ΔfH°liquid | -120.1 ± 1.0 | kJ/mol | Ccb | Hubbard, Douslin, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -118.3 ± 1.0 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4087.7 ± 0.79 | kJ/mol | Ccb | Hubbard, Douslin, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -4085.3 ± 0.79 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 305.01 | 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 |
---|---|---|---|
204.01 | 298.15 | Scott, Finke, et al., 1952 | T = 13 to 300 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:
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 | 425.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 427.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 427.2 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 427. | K | N/A | Mcallan, Cullum, et al., 1951 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 172. | K | N/A | Mcallan, Cullum, et al., 1951 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 171.64 | K | N/A | Scott, Finke, et al., 1952, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 642. | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 45.3 ± 0.4 | kJ/mol | AVG | N/A | Average of 10 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
37.58 | 427.2 | N/A | Majer and Svoboda, 1985 | |
45.7 | 302. | A | Stephenson and Malanowski, 1987 | Based on data from 287. to 434. K.; AC |
40.9 | 388. | EB | Stephenson and Malanowski, 1987 | Based on data from 373. to 431. K. See also Osborn and Douslin, 1966 and Scott, Finke, et al., 1952.; AC |
40.9 ± 0.1 | 373.73 | V | Scott, Finke, et al., 1952, 3 | ALS |
41.5 | 374. | EB | White, Barnard--Smith, et al., 1952 | Based on data from 359. to 433. K.; 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 |
---|---|---|---|---|---|
298. to 400. | 60.92 | 0.2744 | 642. | 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 |
---|---|---|---|---|---|
373.71 to 434.03 | 4.09997 | 1485.97 | -64.192 | Osborn and Douslin, 1966 | |
273. to 353. | 4.3176 | 1605.244 | -53.643 | Scott, Finke, et al., 1952 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.4044 | 171.64 | Scott, Finke, et al., 1952 | DH |
9.4 | 171.6 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
54.79 | 171.64 | Scott, Finke, et al., 1952 | 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 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
B - John E. Bartmess
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.9 | LPES | Carles, Lecomte, et al., 2001 | EA is Vertical Detachment Energy. Adiabtic EA estimated as bound, but only by ca 0.1 eV; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.30 ± 0.15 | EI | Hobrock and Kiser, 1963 | RDSH |
8.27 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.77 | PE | Guimon, Guimon, et al., 1975 | Vertical value; LLK |
8.70 | PE | Wagner and Bock, 1974 | Vertical value; LLK |
8.85 | PE | Baker, Brisk, et al., 1974 | Vertical value; LLK |
8.70 | PE | Bock, Wagner, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
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
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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-3100 |
NIST MS number | 230585 |
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.
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, Douslin, et al., 1958
Hubbard, W.N.; Douslin, D.R.; McCullough, J.P.; Scott, D.W.; Todd, S.S.; Messerly, J.F.; Hossenlopp, I.A.; George, A.; Waddington, G.,
2,3-dithiabutane, 3,4-dithiahexane and 4,5-dithiaoctane: Chemical thermodynamic properties from 0 to 1000°K,
J. Am. Chem. Soc., 1958, 80, 3547-3554. [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]
Scott, Finke, et al., 1952
Scott, D.W.; Finke, H.L.; McCullough, J.P.; Gross, M.E.; Pennington, R.E.; Waddington, G.,
3,4-Dithiahexane: heat capacity, heats of fusion and vaporization, vapor pressure, entropy, and thermodynamic functions,
J. Am. Chem. Soc., 1952, 74, 2478-2483. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]
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]
Scott, Finke, et al., 1952, 2
Scott, D.W.; Finke, H.L.; McCullough, J.P.; Gross, M.E.; Pennington, R.E.; Waddington, G.,
3,4-Dithiahexane: Heat Capacity, Heat of Fusion and Vaporization, Vapor Pressure, Entropy, and Thermodynamic Functions,
J. Am. Chem. Soc., 1952, 74, 2478-83. [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]
Scott, Finke, et al., 1952, 3
Scott, D.W.; Finke, H.L.; McCullough, J.P.; Gross, M.E.; Pennington, R.E.; Waddington, G.,
3,4-Dithiahexane: Heat capacity, heats of fusion and vaporization, vapor pressure, entropy, and thermodynamic functions,
J. Am. Chem. Soc., 1952, 74, 2478-24. [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]
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]
Carles, Lecomte, et al., 2001
Carles, S.; Lecomte, F.; Schermann, J.P.; Desfrancois, C.; Xu, S.; Nilles, J.M.; Bowen, K.H.; Berges, J.; Houe,
Nondissociative electron capture by disulfide bonds,
J. Phys. Chem. A, 2001, 105, 23, 5622-5626, https://doi.org/10.1021/jp0040603
. [all data]
Hobrock and Kiser, 1963
Hobrock, B.G.; Kiser, R.W.,
Electron impact investigations of sulfur compounds. II. 3-Methyl-2-thiabutane, 4-thia-1-pentene, and 3,4-dithiahexane,
J. Phys. Chem., 1963, 67, 648. [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]
Guimon, Guimon, et al., 1975
Guimon, M.-F.; Guimon, C.; Pfister-Guillouzo, G.,
Application of photoelectron spectroscopy to conformational analysis of 1,2,4-trithiolanes,
Tetrahedron Lett., 1975, 7, 441. [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]
Baker, Brisk, et al., 1974
Baker, A.D.; Brisk, M.; Gellender, M.,
Photoelectron spectra and dihedral angles of disulfides,
J. Electron Spectrosc. Relat. Phenom., 1974, 3, 227. [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]
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]
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]
Kiser and Hobrock, 1962
Kiser, R.W.; Hobrock, B.G.,
The ionization potential of hydrogen disulfide (H2S2),
J. Phys. Chem., 1962, 66, 1214. [all data]
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 Tc Critical temperature 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 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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