Di-tert-butyl sulfide
- Formula: C8H18S
- Molecular weight: 146.294
- IUPAC Standard InChIKey: LNMBCRKRCIMQLW-UHFFFAOYSA-N
- CAS Registry Number: 107-47-1
- 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: Propane, 2,2'-thiobis[2-methyl-; tert-Butyl sulfide; 2,2,4,4-Tetramethyl-3-thiapentane; 2,2'-Thiobis(2-methyl-propane); Di-tert-butyl sulphide; (tert-C4H9)2S; t-Butyl sulfide; 2-(tert-Butylsulfanyl)-2-methylpropane; NSC 4549
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Gas phase thermochemistry data
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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -45.05 ± 0.27 | kcal/mol | Ccr | Good, 1972 | |
ΔfH°gas | -44.70 ± 0.65 | kcal/mol | Ccb | Mackle and Mayrick, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -49.6 ± 0.5 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 | -55.51 ± 0.26 | kcal/mol | Ccr | Good, 1972 | |
ΔfH°liquid | -55.62 ± 0.23 | kcal/mol | Ccb | Mackle and Mayrick, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -60.4 ± 0.4 kcal/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1455.63 ± 0.22 | kcal/mol | Ccr | Good, 1972 | |
ΔcH°liquid | -1455.58 ± 0.18 | kcal/mol | Ccb | Mackle and Mayrick, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1450.7 ± 0.4 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 422.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 422.2 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.47 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 10.46 ± 0.05 | kcal/mol | V | Good, 1972 | ALS |
ΔvapH° | 10.5 | kcal/mol | N/A | Good, 1972 | DRB |
ΔvapH° | 10.90 ± 0.22 | kcal/mol | V | Mackle and Mayrick, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = 10.8 ± 0.3 kcal/mol; ALS |
ΔvapH° | 10.9 | kcal/mol | N/A | Mackle and Mayrick, 1962 | DRB |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Reference |
---|---|---|
7.949 | 422.2 | Majer and Svoboda, 1985 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 213.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 206.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.2 ± 0.1 | EI | Distefano, Ricci, et al., 1974 | LLK |
8.07 | PE | Wagner and Bock, 1974 | Vertical value; LLK |
8.18 ± 0.05 | PE | Distefano, Ricci, et al., 1974, 2 | Vertical value; LLK |
8.07 | PE | Bock, Wagner, et al., 1972 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
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 Mayrick, 1962
Mackle, H.; Mayrick, R.G.,
Studies in the thermochemistry of organic sulphides. Part 2. The gas-phase heats of formation of ten aliphatic sulphides,
Trans. Faraday Soc., 1962, 58, 230-237. [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]
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]
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]
Distefano, Ricci, et al., 1974
Distefano, G.; Ricci, A.; Danieli, R.; Foffani, A.; Innorta, G.; Torroni, S.,
Mass spectrometric evidence for p π-d π bonding between sulfur and the Group IVB elements,
J. Organomet. Chem., 1974, 65, 205. [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]
Distefano, Ricci, et al., 1974, 2
Distefano, G.; Ricci, A.; Colonna, F.P.; Pietropaolo, D.; Pignataro, S.,
Bonding between sulfur and the elements of Group IV studied by UV photoelectron spectroscopy,
J. Organomet. Chem., 1974, 78, 93. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
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 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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