3-((1,1-Dimethylethyl)-thio)-1-propene

Formula: C₇H₁₄S
Molecular weight: 130.251
IUPAC Standard InChI: InChI=1S/C7H14S/c1-5-6-8-7(2,3)4/h5H,1,6H2,2-4H3
IUPAC Standard InChIKey: XIBMCVKDUXKQRS-UHFFFAOYSA-N
CAS Registry Number: 37850-75-2
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Allyl tert-butyl sulphide; Allyl sec-butyl sulfide; 5,5-Dimethyl-4-thia-1-hexene
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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	-46. ± 2.	kJ/mol	Ccb	Mackle and Mayrick, 1962	Authors' Ucomb=-948.27 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	-90.7 ± 1.6	kJ/mol	Ccb	Mackle and Mayrick, 1962	Authors' Ucomb=-948.27 kcal/mol
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-5266.6 ± 2.5	kJ/mol	Ccb	Mackle and Mayrick, 1962	Authors' Ucomb=-948.27 kcal/mol

Phase change data

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Data compiled as indicated in comments:
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
Δ_vapH°	44.8	kJ/mol	EB	Mackle and Mayrick, 1962, 2	Based on data from 319. to 339. K.; AC
Δ_vapH°	44. ± 1.	kJ/mol	C	Mackle and Mayrick, 1962	Authors' Ucomb=-948.27 kcal/mol; ALS
Δ_vapH°	44.7	kJ/mol	N/A	Mackle and Mayrick, 1962	DRB

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
41.9	332.	N/A	Dykyj, Svoboda, et al., 1999	Based on data from 319. to 339. K.; AC
43.1	329.	A,EB	Stephenson and Malanowski, 1987	Based on data from 319. to 339. K. See also Mackle and Mayrick, 1962, 2.; AC

Reaction thermochemistry data

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

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Individual Reactions

3-((1,1-Dimethylethyl)-thio)-1-propene =

By formula: C₇H₁₄S = C₇H₁₄S

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-13.7 ± 1.3	kJ/mol	Eqk	Kimmelma, 1988	liquid phase; solvent: DMSO; NMR

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Apiezon M	130.	877.	Garbuzov, Misharina, et al., 1985	He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m
Packed	Apiezon M	130.	877.	Golovnya, Misharina, et al., 1978	Chromosorb W, AW-DMCS; Column length: 2.1 m
Packed	Squalane	100.	855.7	Evans and Smith, 1967	H2/N2=3/1, Celite; Column length: 2. m

References

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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]

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]

Kimmelma, 1988
Kimmelma, R., Structure-stability relationships in vinyl sulfides. III. Stabilization caused by different alkylthio and phenylthio groups attached to an olefinic double bond, Acta Chem. Scand., 1988, 42, 550-555. [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]

Golovnya, Misharina, et al., 1978
Golovnya, R.V.; Misharina, T.A.; Garbuzov, V.G., Gas chromatographic characterization of sulfur-containing compounds. 4. The effect of unsaturated radicals on the retention indices of the vinyl, allyl, and propargyl alkyl sulfides, Izv. Akad. Nauk SSSR Ser. Khim., 1978, 11, 2266-2270. [all data]

Evans and Smith, 1967
Evans, M.B.; Smith, J.F., Gas chromatography in qualitative analysis. IV. An investigation of the changes in relative rentention data accompanying the oxidation of apolar stationary phases, J. Chromatogr., 1967, 28, 277-284, https://doi.org/10.1016/S0021-9673(01)85968-9 . [all data]

Notes

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Symbols used in this document:

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_rH°	Enthalpy of reaction 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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