1,2-Dithiolane

Formula: C₃H₆S₂
Molecular weight: 106.210
IUPAC Standard InChI: InChI=1S/C3H6S2/c1-2-4-5-3-1/h1-3H2
IUPAC Standard InChIKey: MUZIZEZCKKMZRT-UHFFFAOYSA-N
CAS Registry Number: 557-22-2
Chemical structure:
This structure is also available as a 2d Mol file
Other names: 1,2-Dithiacyclopentane
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Other data available:
- Mass spectrum (electron ionization)
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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

+ = 2 + 1,2-Dithiolane

By formula: C₃H₈S₂ + I₂ = 2HI + C₃H₆S₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-107.7	kJ/mol	Cm	Sunner, 1955	liquid phase; solvent: Ethanol/water(90/10)

Gas phase ion energetics data

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Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV)	Method	Reference	Comment
7.6	PE	Bock, Stein, et al., 1980	LLK
8.25	PE	Bock, Stein, et al., 1980	Vertical value; LLK

Gas Chromatography

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

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5	978.	Kubec, Velísek, et al., 1997	30. m/0.25 mm/0.25 μm, N2, 40. C @ 3. min, 4. K/min, 240. C @ 10. min
Capillary	DB-1	960.	Yu, Wu, et al., 1994	60. m/0.25 mm/1. μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 60. min
Capillary	DB-1	963.	Yu, Wu, et al., 1994, 2	60. m/0.25 mm/1. μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 60. min
Capillary	DB-1	963.	Yu, Wu, et al., 1994, 2	60. m/0.25 mm/1. μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 60. min

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

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Column type	Active phase	I	Reference	Comment
Capillary	VF-5	985.	Shivashankar, Roy, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (2 min) 3 0C/min -> 200 0C (3 min) 10 0C/min -> 220 0C (8 min)
Capillary	VF-5	978.	Shivashankar, Roy, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	HP-5	986.	Rotsatschakul, Visesanguan, et al., 2009	60. m/0.25 mm/0.25 μm, Helium; Program: 30 0C (2 min) 2 0Cmin -> 60 0C 10 0C/min -> 100 0C 20 0C/min -> 140 0C 10 0C/min -> 200 0C (10 min)

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax	1523.	Kubec, Velísek, et al., 1997	30. m/0.25 mm/0.5 μm, N2, 40. C @ 3. min, 4. K/min; T_end: 190. C

References

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Sunner, 1955
Sunner, S., Strain in 6,8-thioctic acid, Nature (London), 1955, 176, 217. [all data]

Bock, Stein, et al., 1980
Bock, H.; Stein, U.; Semkov, A., 1,2-Dithiolan - bindungsmodell fur α-liponsaure, Chem. Ber., 1980, 113, 3208. [all data]

Kubec, Velísek, et al., 1997
Kubec, R.; Velísek, J.; Dolezal, M.; Kubelka, V., Sulfur-containing volatiles arising by thermal degradation of alliin and deoxyalliin, J. Agric. Food Chem., 1997, 45, 9, 3580-3585, https://doi.org/10.1021/jf970071q . [all data]

Yu, Wu, et al., 1994
Yu, T.-H.; Wu, C.-M.; Rosen, R.T.; Hartman, T.G.; Ho, C.-T., Volatile compounds in generated from thermal degradation of alliin and deoxyalliin in an aqueous solution, J. Agric. Food Chem., 1994, 42, 1, 146-153, https://doi.org/10.1021/jf00037a026 . [all data]

Yu, Wu, et al., 1994, 2
Yu, T.-H.; Wu, C.-M.; Ho, C.-T., Volatile compounds generated from the thermal interaction of glucose and alliin or deoxyalliin in propylene glycol, Food Chem., 1994, 51, 3, 281-286, https://doi.org/10.1016/0308-8146(94)90028-0 . [all data]

Shivashankar, Roy, et al., 2012
Shivashankar, S.; Roy, T.K.; Moorthy, P.N.R., Headspace solid phase micro extraction and GC/MS analysis of the volatile components in seed and cake of Azadirachta indica A. juss, Chem. Bull. of Politechnika Univ. Timisoara, Romania, 2012, 57(71), 1, 1-6. [all data]

Rotsatschakul, Visesanguan, et al., 2009
Rotsatschakul, P.; Visesanguan, W.; Smitinont, T.; Chaiseri, S., Changes in volatile compounds during fermentation of nham (Thai fermented sausage), Int. Food Res. J., 2009, 16, 391-414. [all data]

Notes

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Symbols used in this document:

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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