Di-tert-butyl sulfide

Formula: C₈H₁₈S
Molecular weight: 146.294
IUPAC Standard InChI: InChI=1S/C8H18S/c1-7(2,3)9-8(4,5)6/h1-6H3
IUPAC Standard InChIKey: LNMBCRKRCIMQLW-UHFFFAOYSA-N
CAS Registry Number: 107-47-1
Chemical structure:
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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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Other data available:
- Gas phase ion energetics data
- Mass spectrum (electron ionization)
Data at other public NIST sites:
- Gas Phase Kinetics Database
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-45.05 ± 0.27	kcal/mol	Ccr	Good, 1972
Δ_fH°_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 compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-55.51 ± 0.26	kcal/mol	Ccr	Good, 1972
Δ_fH°_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
Δ_cH°_liquid	-1455.63 ± 0.22	kcal/mol	Ccr	Good, 1972
Δ_cH°_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 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
T_boil	422.2	K	N/A	Weast and Grasselli, 1989	BS
T_boil	422.2	K	N/A	Majer and Svoboda, 1985
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	10.47	kcal/mol	N/A	Majer and Svoboda, 1985
Δ_vapH°	10.46 ± 0.05	kcal/mol	V	Good, 1972	ALS
Δ_vapH°	10.5	kcal/mol	N/A	Good, 1972	DRB
Δ_vapH°	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
Δ_vapH°	10.9	kcal/mol	N/A	Mackle and Mayrick, 1962	DRB

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Reference
7.949	422.2	Majer and Svoboda, 1985

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Apiezon M	130.	918.	Garbuzov, Misharina, et al., 1985	He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m
Packed	Apiezon L	110.	913.	Martinu and Janák, 1970
Packed	Apiezon L	130.	920.	Martinu and Janák, 1970
Packed	Apiezon L	150.	927.	Martinu and Janák, 1970

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Apiezon M	918.	Liu, Cao, et al., 2005	Program: not specified
Packed	Apiezon M	918.	Yu and Yang, 2005	Program: not specified
Capillary	CP Sil 5 CB	905.	Gijs, Piraprez, et al., 2000	50. m/0.32 mm/1.2 μm, He; Program: 33C (16.5min) => 2C/min => 160C => 20C/min => 200C (9min)

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes

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]

Garbuzov, Misharina, et al., 1985
Garbuzov, V.G.; Misharina, T.A.; Aerov, A.F.; Golovnya, R.V., Gas chromatographic retention indices for sulphur(II)-containing organic substances, J. Anal. Chem. USSR (Engl. Transl.), 1985, 40, 4, 576-586. [all data]

Martinu and Janák, 1970
Martinu, V.; Janák, J., Gas-liquid chromatographic retention data of some aliphatic and alicyclic sulphides, J. Chromatogr., 1970, 52, 69-75, https://doi.org/10.1016/S0021-9673(01)96545-8 . [all data]

Liu, Cao, et al., 2005
Liu, L.; Cao, C.-Z.; Xie, B.; Zou, L.-K., Research of QSSR on chromatography retention index of sulfides and mercaptans, Journal of Hunan University of Science and Technology, 2005, 20, 4, 74-80. [all data]

Yu and Yang, 2005
Yu, X.; Yang, D., Predicting the Kovats retention index for alkoxyl silicon chlorides and sulfides on stationary phases of different polarity, Fenxi Huaxue, 2005, 33, 1, 101-105. [all data]

Gijs, Piraprez, et al., 2000
Gijs, L.; Piraprez, G.; Perpète, P.; Spinnler, E.; Collin, S., Retention of sulfur flavours by food matrix and determination of sensorial data independent of the medium composition, Food Chem., 2000, 69, 3, 319-330, https://doi.org/10.1016/S0956-7135(99)00111-5 . [all data]

Notes

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Symbols used in this document:

T_boil	Boiling point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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