Thiophene, tetrahydro-

• Formula: C₄H₈S
• Molecular weight: 88.171
• IUPAC Standard InChI: InChI=1S/C4H8S/c1-2-4-5-3-1/h1-4H2 Copy

  
• IUPAC Standard InChIKey: RAOIDOHSFRTOEL-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-01-0
• 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: Tetramethylene sulfide; Tetrahydrothiophene; Tetrahydrothiophen; Thiacyclopentane; Thilane; Thiolane; Thiophane; Tetramethylene sulphide; Thiolan; THT; Tetrahydrothiofen; Thiofan; UN 2412; Pennodorant 1013; NSC 5272
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• Information on this page:
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • UV/Visible spectrum
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  • Gas Phase Kinetics Database
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Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₄H₈S⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Butler and Baer, 1983
Butler, J.J.; Baer, T., A photoionization study of organosulfur ring compounds: Thiirane, thietane and tetrahydrothiophene, Org. Mass Spectrom., 1983, 18, 248. [all data]

Distefano, Foffani, et al., 1971
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S., Mass spectrometric study of transition metal complexes with ligands having nitrogen or sulphur as donor atom, Adv. Mass Spectrom., 1971, 5, 696. [all data]

Distefano, Foffani, et al., 1971, 2
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S., Electron impact ionization potentials of some manganese, chromium and tungsten organometallic derivatives, Int. J. Mass Spectrom. Ion Phys., 1971, 7, 383. [all data]

Gallegos and Kiser, 1962
Gallegos, E.J.; Kiser, R.W., Electron impact spectroscopy of the four- and five-membered, saturated heterocyclic compounds containing nitrogen, oxygen and sulfur, J. Phys. Chem., 1962, 66, 136. [all data]

Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A., Ausschluss transanularer Wechselwirkung in 2.5-Dihydrothiophen, Tetrahedron Lett., 1973, 1437. [all data]

Butler and Baer, 1982
Butler, J.J.; Baer, T., Photoionization study of the heat of formation of HCS⁺, J. Am. Chem. Soc., 1982, 104, 5016. [all data]

Miller and Bruno, 2003
Miller, K.E.; Bruno, T.J., Isothermal Kováts retention indices of sulfur compounds on a poly(5% diphenyl-95% dimethylsiloxane) stationary phase, J. Chromatogr. A, 2003, 1007, 1-2, 117-125, https://doi.org/10.1016/S0021-9673(03)00958-0 . [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]

Gal'pern, Gollandskikh, et al., 1976
Gal'pern, G.D.; Gollandskikh, N.I.; Gordadze, G.N., Application of methylene-insertion reactions to cyclic sulphides (C₄H₈S, C₅H₁₀S and C₆H₁₂S) to produce standard compounds for gas chromatography, J. Chromatogr., 1976, 124, 1, 43-51, https://doi.org/10.1016/S0021-9673(00)87835-8 . [all data]

Agr, Tesaric, et al., 1973
Agr, X.X.; Tesaric, K.; Janak, J., Will be entered later, J. Chromatogr., 1973, 95, 207-215. [all data]

Agrawal, Tesarík, et al., 1972
Agrawal, B.B.; Tesarík, K.; Janák, J., Gas chromatographic characterization of sulphur compounds in the 93-162° gasoline cut from Romashkino crude oil using Kováts retention indices, J. Chromatogr., 1972, 65, 1, 207-215, https://doi.org/10.1016/S0021-9673(00)86933-2 . [all data]

Safa and Hadjmohannadi, 2005
Safa, F.; Hadjmohannadi, M.R., Use of topological indices of organic sulfur compounds in quantitative structure-retention relationship study, QSAR Comb. Sci., 2005, 24, 9, 1026-1032, https://doi.org/10.1002/qsar.200530008 . [all data]

Blazevic and Mastelic, 2008
Blazevic, I.; Mastelic, J., Free and bounded volatiles of rocket (Eruca sativa Mill.), Fravour Fragr. J., 2008, 23, 4, 278-285, https://doi.org/10.1002/ffj.1883 . [all data]

Yang, Wang, et al., 2003
Yang, Y.-T.; Wang, Z.; Han. J.-H.; Tian, H.-P.; Yang, H.-Y., Determination of sulfur compounds in gasoline fraction of microreactor products by gas chromatography - Atomic emission detector, Petrochemical Technology (Shiyou Huagong), 2003, 32, 11, 995-998. [all data]

Yang, Yang, et al., 2003
Yang, Y.T.; Yang, H.Y.; Zong, B.N.; Lu, W.Z., determination and distribution of sulfur compounds in gasoline by gas chromatography-atomic emission detector, Chinise J. Anal. Chem. (Fenxi Huaxue), 2003, 31, 10, 1153-1158. [all data]

Jirovetz, Smith, et al., 2002
Jirovetz, L.; Smith, D.; Buchbauer, G., Aroma compound analysis of Eruca sativa (Brassicaceae) SPME headspace leaf samples using GC, GC-MS, and olfactometry, J. Agric. Food Chem., 2002, 50, 16, 4643-4646, https://doi.org/10.1021/jf020129n . [all data]

Egolf and Jurs, 1993
Egolf, L.M.; Jurs, P.C., Quantitative structure-retention and structure-odor intensity relationships for a diverse group of odor-active compounds, Anal. Chem., 1993, 65, 21, 3119-3126, https://doi.org/10.1021/ac00069a027 . [all data]

Damste, van Dalen, et al., 1988
Damste, J.S.S.; van Dalen, A.C.K.; de Leeuw, J.W.; Schenck, P.A., Identification of homologous series of alkylated thiophenes, thiolanes, thianes and benzothiophenes present in pyrolisates of sulfur-rich kerogenes, J. Chromatogr., 1988, 435, 435-452, https://doi.org/10.1016/S0021-9673(01)82208-1 . [all data]

Damste, Kock-van Dalen, et al., 1988
Damste, J.S.S.; Kock-van Dalen, A.C.; de Leeuw, J.W.; Schenk, P.A., Identification of homologous series of alkylated thiophenes, thiolanes, thianes and benzothiophenes present in pyrolysates of sulphur-rich kerogens, J. Chromatogr., 1988, 435, 435-452, https://doi.org/10.1016/S0021-9673(01)82208-1 . [all data]

Farkas, Héberger, et al., 2004
Farkas, O.; Héberger, K.; Zenkevich, I.G., Quantitative structure-retention relationships. XIV. Prediction of gas chromatographic retention indices for saturated O-, N-, and S-heterocyclic compounds, Chemom. Intell. Lab. Syst., 2004, 72, 2, 173-184, https://doi.org/10.1016/j.chemolab.2004.01.012 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

P'yanova, Zvereva, et al., 1987
P'yanova, V.P.; Zvereva, M.N.; Tsypysheva, LG.; Portnova, T.V.; Kruglov, E.A., Investigating the products of thiophane synthesis, Abstr. IX All-Union Conference on Gas Chromatography, Kuibyshev State University, Kuibyshev, 1987, 308. [all data]

van Langenhove and Schamp, 1986
van Langenhove, H.; Schamp, N., Identification of Volatiles in the Head Space of Acid-Treated Phosphate Rock by Gas Chromatography-Mass Spectromety, J. Chromatogr., 1986, 351, 65-75, https://doi.org/10.1016/S0021-9673(01)83473-7 . [all data]

Umano, Hagi, et al., 1995
Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T., Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system, J. Agric. Food Chem., 1995, 43, 8, 2212-2218, https://doi.org/10.1021/jf00056a046 . [all data]

Notes

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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