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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry 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 compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Reaction thermochemistry 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 compiled by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

(C₄H₈S⁺ • ) +  = (C₄H₈S⁺ • 2)

By formula: (C₄H₈S⁺ • C₄H₈S) + C₄H₈S = (C₄H₈S⁺ • 2C₄H₈S)

(C₄H₉S⁺ • ) +  = (C₄H₉S⁺ • 2)

By formula: (C₄H₉S⁺ • C₄H₈S) + C₄H₈S = (C₄H₉S⁺ • 2C₄H₈S)

C₄H₉S⁺ +  = (C₄H₉S⁺ • )

By formula: C₄H₉S⁺ + C₄H₈S = (C₄H₉S⁺ • C₄H₈S)

C₄H₈S⁺ +  = (C₄H₈S⁺ • )

By formula: C₄H₈S⁺ + C₄H₈S = (C₄H₈S⁺ • C₄H₈S)

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

Ion clustering 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 compiled by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₄H₈S⁺ +  = (C₄H₈S⁺ • )

By formula: C₄H₈S⁺ + C₄H₈S = (C₄H₈S⁺ • C₄H₈S)

(C₄H₈S⁺ • ) +  = (C₄H₈S⁺ • 2)

By formula: (C₄H₈S⁺ • C₄H₈S) + C₄H₈S = (C₄H₈S⁺ • 2C₄H₈S)

C₄H₉S⁺ +  = (C₄H₉S⁺ • )

By formula: C₄H₉S⁺ + C₄H₈S = (C₄H₉S⁺ • C₄H₈S)

(C₄H₉S⁺ • ) +  = (C₄H₉S⁺ • 2)

By formula: (C₄H₉S⁺ • C₄H₈S) + C₄H₈S = (C₄H₉S⁺ • 2C₄H₈S)

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

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

Davies and Sunner, 1962
Davies, J.V.; Sunner, S., Heats of combustion and formation of thiolane and of the thiolenes, Acta Chem. Scand., 1962, 16, 1870-1876. [all data]

Sunner, 1963
Sunner, S., Corrected heat of combustion and formation values for a number of organic sulphur compounds, Acta Chem. Scand., 1963, 17, 728-730. [all data]

Hubbard, Katz, et al., 1954
Hubbard, W.N.; Katz, C.; Waddington, G., A rotating combustion bomb for precision calorimetry. Heats of combustion of some sulfur-containing compounds, J. Phys. Chem., 1954, 58, 142. [all data]

Hiraoka, Takimoto, et al., 1987
Hiraoka, K.; Takimoto, H.; Yamabe, S., Stabilities and Structures in Cluster Ions of Five-Membered Heterocyclic Compounds Containing O, N and S Atoms, J. Am. Chem. Soc., 1987, 109, 24, 7346, https://doi.org/10.1021/ja00258a018 . [all data]

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 thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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