Di-tert-butyl disulfide
- Formula: C8H18S2
- Molecular weight: 178.359
- IUPAC Standard InChI: InChI=1S/C8H18S2/c1-7(2,3)9-10-8(4,5)6/h1-6H3
- IUPAC Standard InChIKey: BKCNDTDWDGQHSD-UHFFFAOYSA-N
- CAS Registry Number: 110-06-5
- 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, bis(1,1-dimethylethyl); tert-Butyl disulfide; Bis(1,1-dimethylethyl) disulfide; 2,2,5,5-Tetramethyl-3,4-dithiahexane; Di-tert-butyl disulphide; Bis(1,1-dimethylethyl) disulphide; (tert-C4H9S)2; t-Butyl disulfide; 2-(tert-Butyldisulfanyl)-2-methylpropane
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction 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 | -47.8 | kcal/mol | Ion | Hawari, Griller, et al., 1986 | |
| ΔfH°gas | -47.75 ± 0.54 | kcal/mol | Ccr | Good, 1972 | |
| ΔfH°gas | -48.29 ± 0.54 | kcal/mol | Ccb | Mackle and McClean, 1964 | Reanalyzed by Cox and Pilcher, 1970, Original value = -47.05 ± 0.60 kcal/mol |
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°liquid | -60.46 ± 0.36 | kcal/mol | Ccr | Good, 1972 | |
| ΔfH°liquid | -60.00 ± 0.42 | kcal/mol | Ccb | Mackle and McClean, 1964 | Reanalyzed by Cox and Pilcher, 1970, Original value = -59.76 ± 0.39 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1594.16 ± 0.32 | kcal/mol | Ccr | Good, 1972 | |
| ΔcH°liquid | -1595.16 ± 0.38 | kcal/mol | Ccb | Mackle and McClean, 1964 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1593.42 ± 0.38 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:
BS - Robert L. Brown and Stephen E. Stein
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 | 473.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 12.6 ± 0.7 | kcal/mol | AVG | N/A | Average of 8 values; Individual data points |
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference | Comment |
|---|---|---|---|
| 361.2 | 0.028 | Weast and Grasselli, 1989 | BS |
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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
+
= 2
By formula: C8H18S2 + C4H10S2 = 2C6H14S2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 0.0 ± 0.05 | kcal/mol | Eqk | Haraldson, Olander, et al., 1960 | liquid phase; solvent: Nonpolar solvent |
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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.15 | PE | Guimon, Guimon, et al., 1975 | Vertical value; LLK |
| 8.17 | PE | Wagner and Bock, 1974 | Vertical value; LLK |
| 8.20 | PE | Baker, Brisk, et al., 1974 | Vertical value; LLK |
| 8.17 | PE | Bock, Wagner, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C4H9S2+ | 9.1 ± 0.8 | (CH3)3C | EI | Hawari, Griller, et al., 1986, 2 | LBLHLM |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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.
Hawari, Griller, et al., 1986
Hawari, J.A.; Griller, D.; Lossing, F.P.,
Thermochemistry of perthiyl radicals,
J. Am. Chem. Soc., 1986, 108, 3273-3275. [all data]
Good, 1972
Good, W.D.,
Enthalpies of combustion of 18 organic sulfur compounds related to petroleum,
J. Chem. Eng. Data, 1972, 17, 158-162. [all data]
Mackle and McClean, 1964
Mackle, H.; McClean, R.T.B.,
Studies in the thermochemistry of organic sulphides. Part 5.-Dithia-alkanes,
Trans. Faraday Soc., 1964, 60, 669-672. [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]
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]
Haraldson, Olander, et al., 1960
Haraldson, L.; Olander, C.J.; Sunner, S.; Varde, K.,
Equilibrium studies on the disproportionation reaction between some dialkyl disulfides,
Acta Chem. Scand., 1960, 14, 1509-1514. [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]
Hawari, Griller, et al., 1986, 2
Hawari, J.A.; Griller, D.; Lossing, F.P.,
Thermochemistry of perthiyl radicals,
J. Am. Chem. Soc., 1986, 108, 3273. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point 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 ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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