Disulfide, diphenyl
- Formula: C12H10S2
- Molecular weight: 218.338
- IUPAC Standard InChIKey: GUUVPOWQJOLRAS-UHFFFAOYSA-N
- CAS Registry Number: 882-33-7
- 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: Phenyl disulfide; Diphenyl disulfide; USAF e-1; diphenyl disulphide
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Gas 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 246.0 | kJ/mol | N/A | Metzger, Kuo, et al., 1983 | Value computed using ΔfHsolid° value of 151.1 kj/mol from Metzger, Kuo, et al., 1983 and ΔsubH° value of 94.9 kj/mol from Mackle and Mayrick, 1962.; DRB |
ΔfH°gas | 244. ± 4.2 | kJ/mol | Ccb | Mackle and Mayrick, 1962 | Hfusion=3.9±0.5 kcal/mol; ALS |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 151.06 | kJ/mol | Ccr | Metzger, Kuo, et al., 1983 | |
ΔfH°solid | 149.1 ± 2.7 | kJ/mol | Ccb | Mackle and Mayrick, 1962 | Hfusion=3.9±0.5 kcal/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -7503.18 | kJ/mol | Ccr | Metzger, Kuo, et al., 1983 | |
ΔcH°solid | -7504.4 ± 2.7 | kJ/mol | Ccb | Mackle and Mayrick, 1962 | Hfusion=3.9±0.5 kcal/mol |
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:
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 |
---|---|---|---|---|---|
Tfus | 333.5 | K | N/A | Snyder and Geller, 1952 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 78.7 ± 2.9 | kJ/mol | N/A | Mackle and Mayrick, 1962, 2 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 95. ± 2. | kJ/mol | C | Mackle and Mayrick, 1962 | Hfusion=3.9±0.5 kcal/mol; ALS |
ΔsubH° | 94.9 | kJ/mol | N/A | Mackle and Mayrick, 1962 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
72.4 | 420. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 405. to 583. K.; AC |
74.4 | 419. | A | Stephenson and Malanowski, 1987 | Based on data from 404. to 583. K. See also Stull, 1947.; AC |
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 |
---|---|---|---|---|---|
404.8 to 583. | 6.77301 | 4039.907 | 14.034 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.4 ± 0.3 | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
8.3 | PE | Giordon and Bock, 1982 | Vertical value; LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHS+ | 21.0 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C2H3S+ | 20.5 ± 0.3 | ? | EI | Bogolyubov, Plotnikov, et al., 1969 | RDSH |
C3H3S+ | 18.6 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C4H2+ | 23.6 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C4H3+ | 20.5 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C4H3S+ | 19.0 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C4H4S+ | 14.1 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C5H3+ | 22.2 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C5H4S+ | 15.5 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C5H5S+ | 17.2 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C6H5S+ | 14.4 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C6H6S+ | 11.6 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C11H7S+ | 13.8 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C12H8S+ | 14.8 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C12H9S+ | 12.6 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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
Spectrum
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Additional Data
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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 | Chemical Concepts |
NIST MS number | 185623 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, NIST Subscription Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Metzger, Kuo, et al., 1983
Metzger, R.M.; Kuo, C.S.; Arafat, E.S.,
A semi-micro rotating-bomb combustion calorimeter,
J. Chem. Thermodyn., 1983, 15, 841-851. [all data]
Mackle and Mayrick, 1962
Mackle, H.; Mayrick, R.G.,
Studies in thermochemistry of organic sulphides. Part 3.-The gas-phase heats of formation of diphenyl sulphide, dibenzyl sulphide, diphenyl disulphide,4-thia-1-hexene and 4-thia-5,5-dimethyl-1-hexene,
Trans. Faraday Soc., 1962, 58, 238-243. [all data]
Snyder and Geller, 1952
Snyder, H.R.; Geller, H.C.,
Cleavage of Sulfonamides with Aqueous Hydrobromic Acid and Phenol II.,
J. Am. Chem. Soc., 1952, 74, 4864. [all data]
Mackle and Mayrick, 1962, 2
Mackle, H.; Mayrick, R.G.,
Studies in the thermochemistry of organic sulphides. Part 3.?The gas-phase heats of formation of diphenyl sulphide, dibenzyl sulphide, diphenyl disulphide, 4-thia-1-hexene and 4-thia-5,5-dimethyl-1-hexene,
Trans. Faraday Soc., 1962, 58, 238, https://doi.org/10.1039/tf9625800238
. [all data]
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
. [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]
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]
Giordon and Bock, 1982
Giordon, J.; Bock, H.,
Radical ions, 51. Oxidative rearrangement of diphenyl disulfides to thianthrenes,
Chem. Ber., 1982, 115, 2548. [all data]
Bogolyubov, Plotnikov, et al., 1969
Bogolyubov, G.M.; Plotnikov, V.F.; Boiko, Yu.A.; Petrov, A.A.,
Organic derivatives of elements of groups V and VI. IX. Mass spectra of vinylacetylene sulfides,
Zh. Obshch. Khim., 1969, 39, 2467, In original 2407. [all data]
Notes
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- Symbols used in this document:
AE Appearance energy Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔsubH° Enthalpy of sublimation 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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