1,4-Dithiane

Formula: C₄H₈S₂
Molecular weight: 120.236
IUPAC Standard InChI: InChI=1S/C4H8S2/c1-2-6-4-3-5-1/h1-4H2
IUPAC Standard InChIKey: LOZWAPSEEHRYPG-UHFFFAOYSA-N
CAS Registry Number: 505-29-3
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: p-Dithiane; p-Dithiin, tetrahydro-; 1,4-Dithiin, tetrahydro-; para-Dithiane; 1,4-Dithiacyclohexane
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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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.8 ± 0.1	EI	Conde-Caprace and Collin, 1969	RDSH
8.5	EI	Kiser and Gallegos, 1962	RDSH
8.58	PE	Sweigart and Turner, 1972	Vertical value; LLK
8.46	PE	Bock, Wagner, et al., 1972	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CH₂S⁺	13. ± 0.3	?	EI	Conde-Caprace and Collin, 1969	RDSH
C₂H₄S⁺	10.9 ± 0.2	?	EI	Conde-Caprace and Collin, 1969	RDSH
C₂H₄S₂⁺	11.0 ± 0.1	?	EI	Conde-Caprace and Collin, 1969	RDSH
C₂H₅S⁺	10.6 ± 0.2	?	EI	Conde-Caprace and Collin, 1969	RDSH
C₃H₅S⁺	10.7 ± 0.1	?	EI	Conde-Caprace and Collin, 1969	RDSH
C₃H₅S₂⁺	10. ± 0.	?	EI	Conde-Caprace and Collin, 1969	RDSH
C₃H₆S⁺	11.4 ± 0.2	?	EI	Conde-Caprace and Collin, 1969	RDSH
S₂⁺	12.4 ± 0.2	2C₂H₄	EI	Conde-Caprace and Collin, 1969	RDSH

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
Capillary	Methyl Silicone	100.	1038.	Huber, Kenndler, et al., 1993	H2; Column length: 5. m; Phase thickness: 2.65 μm
Capillary	Methyl Silicone	120.	1050.	Huber, Kenndler, et al., 1993	H2; Column length: 5. m; Phase thickness: 2.65 μm
Packed	Apiezon M	130.	1094.	Garbuzov, Misharina, et al., 1985	He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m

Kovats' RI, polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	PEG-20M	130.	1618.	Huber, Kenndler, et al., 1993	Column length: 10. m; Phase thickness: 1.33 μm
Capillary	PEG-20M	150.	1641.	Huber, Kenndler, et al., 1993	Column length: 10. m; Phase thickness: 1.33 μm
Capillary	PEG-20M	130.	1618.9	Huber, Kenndler, et al., 1993	Column length: 10. m; Phase thickness: 1.33 μm

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	OV-1	1019.	Kostiainen, 2000	15. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 10. K/min, 280. C @ 10. min
Capillary	SE-54	1068.	Kostiainen, 2000	25. m/0.32 mm/0.25 μm, He, 40. C @ 1. min, 10. K/min, 280. C @ 10. min
Capillary	DB-1	1028.	Hancock and Peters, 1991	He, 50. C @ 2. min, 10. K/min; Column length: 15. m; Column diameter: 0.53 mm
Capillary	DB-5	1067.7	Hancock and Peters, 1991	He, 50. C @ 2. min, 10. K/min; Column length: 15. m; Column diameter: 0.53 mm
Capillary	DB-1	1019.	D'agostino and Provost, 1988	15. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 10. K/min, 300. C @ 5. min
Capillary	DB-5	1060.2	D'agostino and Provost, 1988	15. m/0.32 mm/0.25 μm, 50. C @ 2. min, 10. K/min, 300. C @ 5. min
Capillary	DB-1	1018.7	D'Agostino and Provost, 1985	15. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 10. K/min, 300. C @ 5. min
Capillary	DB-5	1060.2	D'Agostino and Provost, 1985	15. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 10. K/min; T_end: 300. C

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1575.7	D'Agostino and Provost, 1985	15. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 10. K/min, 250. C @ 5. min

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1074.	Hanaoka, Nomura, et al., 2006	30. m/0.32 mm/0.25 μm, He, 100. C @ 5. min, 10. K/min; T_end: 280. C
Capillary	HP-5	1022.	Mazurek, Witkiewicz, et al., 2001	He, 40. C @ 3. min, 10. K/min, 280. C @ 30. min; Column length: 30. m; Column diameter: 0.32 mm

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-1	1019.	Tarjan, Nyiredy, et al., 1989	Program: not specified

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.	1576.	Waggott and Davies, 1984	Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes

Conde-Caprace and Collin, 1969
Conde-Caprace, G.; Collin, J.E., Ionization and dissociation of cyclic ethers and thioethers by electronimpact. A comparison between 1,4 dioxane, 1,4 dithiane and 1,4 oxathiane, Org. Mass Spectrom., 1969, 2, 1277. [all data]

Kiser and Gallegos, 1962
Kiser, R.W.; Gallegos, E.J., A technique for the rapid determination of ionization and appearance potentials, J. Phys. Chem., 1962, 66, 947. [all data]

Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W., Lone pair orbitals and their interactions studied by photoelectron spectroscopy. II. Equivalent orbitals in saturated oxygen and sulfur J. Heterocycl. Chem., J. Am. Chem. Soc., 1972, 94, 5599. [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]

Huber, Kenndler, et al., 1993
Huber, J.F.K.; Kenndler, E.; Reich, G.; Hack, W.; Wolf, J., Optimal Selection of Gas Chromatographic Columns for the Analytical Control of Chemical Warfare Agents by Application of Information Theory to Retention Data, Anal. Chem., 1993, 65, 20, 2903-2906, https://doi.org/10.1021/ac00068a031 . [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]

Kostiainen, 2000
Kostiainen, O., Gas Chromatography in Screening of Chemicals Related to the Chemical Weapons Convention in Encyclopedia of Analytical Chemistry, Meyers, R.A., ed(s)., John Wiley Sons Ltd, Chichester, 2000, 963-979. [all data]

Hancock and Peters, 1991
Hancock, J.R.; Peters, G.R., Retention index monitoring of compounds of chemical defence interest using thermal desorption gas chromatography, J. Chromatogr., 1991, 538, 2, 249-257, https://doi.org/10.1016/S0021-9673(01)88845-2 . [all data]

D'agostino and Provost, 1988
D'agostino, P.A.; Provost, L.R., Gas chromatographic retention indices of sulphur vesicants and related compounds, J. Chromatogr., 1988, 436, 399-411, https://doi.org/10.1016/S0021-9673(00)94599-0 . [all data]

D'Agostino and Provost, 1985
D'Agostino, P.A.; Provost, L.R., Gas chromatographic retention indices of chemical warfare agents and simulants, J. Chromatogr., 1985, 331, 47-54, https://doi.org/10.1016/0021-9673(85)80005-4 . [all data]

Hanaoka, Nomura, et al., 2006
Hanaoka, S.; Nomura, K.; Wada, T., Determination of mustard and lewisite related compounds in abandoned chemical weapons (Yellow shells) from sources in China and Japan, J. Chromatogr. A, 2006, 1101, 1-2, 268-277, https://doi.org/10.1016/j.chroma.2005.10.028 . [all data]

Mazurek, Witkiewicz, et al., 2001
Mazurek, M.; Witkiewicz, Z.; Popiel, S.; Sliwakowski, M., Capillary gas chromatography-atomic emission spectroscopy-mass spectrometry analysis of sulphur mustard and transformation products in a block recovered from the Baltic Sea, J. Chromatogr. A, 2001, 919, 1, 133-145, https://doi.org/10.1016/S0021-9673(01)00672-0 . [all data]

Tarjan, Nyiredy, et al., 1989
Tarjan, G.; Nyiredy, Sz.; Gyor, M.; Lombosi, E.R.; Lombosi, T.S.; Budahegyi, M.V.; Meszaros, S.Y.; Takacs, J.M., Review. Thirtieth Anniversary of the Retention Index According to Kovats in Gas-Liquid Chromatography, J. Chromatogr., 1989, 472, 1-92, https://doi.org/10.1016/S0021-9673(00)94099-8 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Notes

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Symbols used in this document:

AE Appearance energy
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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