Thiophene, tetrahydro-
- Formula: C4H8S
- Molecular weight: 88.171
- IUPAC Standard InChIKey: RAOIDOHSFRTOEL-UHFFFAOYSA-N
- 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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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes
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
By formula: (C4H8S+ • C4H8S) + C4H8S = (C4H8S+ • 2C4H8S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 33. | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 75. | J/mol*K | N/A | Hiraoka, Takimoto, et al., 1987 | gas phase; Entropy change calculated or estimated |
By formula: (C4H9S+ • C4H8S) + C4H8S = (C4H9S+ • 2C4H8S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 33. | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 75. | J/mol*K | N/A | Hiraoka, Takimoto, et al., 1987 | gas phase; Entropy change calculated or estimated |
By formula: C4H9S+ + C4H8S = (C4H9S+ • C4H8S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 70.7 | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 87.9 | J/mol*K | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase |
By formula: C4H8S+ + C4H8S = (C4H8S+ • C4H8S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 70.7 | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; ΔrH< |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, Gas Chromatography, References, Notes
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.38 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 849.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 819.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.38 | PIPECO | Butler and Baer, 1983 | LBLHLM |
8.62 ± 0.05 | EI | Distefano, Foffani, et al., 1971 | LLK |
8.62 | EI | Distefano, Foffani, et al., 1971, 2 | LLK |
8.57 ± 0.15 | EI | Gallegos and Kiser, 1962 | RDSH |
8.40 | PE | Schmidt and Schweig, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHS+ | 11.0 ± 0.1 | C3H7 | PI | Butler and Baer, 1982 | T = 298K; LBLHLM |
CHS+ | 11.1 ± 0.1 | C3H7 | PI | Butler and Baer, 1982 | T = 0K; LBLHLM |
CHS+ | 13.8 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
CH2S+ | 10.5 | C3H6 | PIPECO | Butler and Baer, 1983 | LBLHLM |
CH2S+ | 13.0 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
CH3S+ | 11.1 | C3H5 | PIPECO | Butler and Baer, 1983 | LBLHLM |
CH3S+ | 14.0 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H2S+ | 17.0 ± 0.3 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H3+ | 18.0 ± 0.4 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H3S+ | 10.36 | C2H5 | PIPECO | Butler and Baer, 1983 | LBLHLM |
C2H3S+ | 15.7 ± 0.4 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H4S+ | 11.7 ± 0.3 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C3H3+ | 17.2 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C3H5+ | 15.5 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C4H6+ | 11.9 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C4H7+ | 12.4 ± 0.2 | SH | EI | Gallegos and Kiser, 1962 | RDSH |
C4H7S+ | 10.1 | H | PIPECO | Butler and Baer, 1983 | LBLHLM |
C4H7S+ | 12.4 ± 0.3 | H | EI | Gallegos and Kiser, 1962 | RDSH |
C4H8S+ | 10.21 | C2H4 | PIPECO | Butler and Baer, 1983 | LBLHLM |
Gas Chromatography
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | DB-5 | 100. | 821.0 | Miller and Bruno, 2003 | 30. m/0.25 mm/0.1 μm |
Capillary | DB-5 | 120. | 832.5 | Miller and Bruno, 2003 | 30. m/0.25 mm/0.1 μm |
Capillary | DB-5 | 60. | 806.3 | Miller and Bruno, 2003 | 30. m/0.25 mm/0.1 μm |
Capillary | DB-5 | 80. | 812.6 | Miller and Bruno, 2003 | 30. m/0.25 mm/0.1 μm |
Packed | Apiezon M | 130. | 834. | Garbuzov, Misharina, et al., 1985 | He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m |
Capillary | OV-101 | 100. | 805. | Gal'pern, Gollandskikh, et al., 1976 | H2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Apiezon L | 120. | 839. | Agr, Tesaric, et al., 1973 | |
Capillary | Squalane | 120. | 775. | Agr, Tesaric, et al., 1973 | |
Capillary | Squalane | 86. | 772. | Agr, Tesaric, et al., 1973 | |
Capillary | Apiezon L | 120. | 839. | Agrawal, Tesarík, et al., 1972 | N2; Column length: 100. m; Column diameter: 0.3 mm |
Capillary | Squalane | 120. | 775. | Agrawal, Tesarík, et al., 1972 | N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm |
Capillary | Squalane | 86. | 772. | Agrawal, Tesarík, et al., 1972 | N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Polydimethyl siloxane with 5 % Ph groups | 100. | 821. | Safa and Hadjmohannadi, 2005 | 30. m/0.25 mm/0.10 μm, Nitrogen |
Capillary | Polydimethyl siloxane with 5 % Ph groups | 60. | 806. | Safa and Hadjmohannadi, 2005 | 30. m/0.25 mm/0.10 μm, Nitrogen |
Capillary | Polydimethyl siloxane with 5 % Ph groups | 80. | 813. | Safa and Hadjmohannadi, 2005 | 30. m/0.25 mm/0.10 μm, Nitrogen |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-101 | 838. | Blazevic and Mastelic, 2008 | 25. m/0.20 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min; Tend: 200. C |
Capillary | PONA | 779. | Yang, Wang, et al., 2003 | 50. m/0.20 mm/0.50 μm, 2. K/min; Tstart: 30. C; Tend: 150. C |
Capillary | PONA | 782. | Yang, Yang, et al., 2003 | 50. m/0.20 mm/0.50 μm, Helium, 2. K/min; Tstart: 30. C; Tend: 170. C |
Capillary | RSL-200 | 802. | Jirovetz, Smith, et al., 2002 | 30. m/0.25 mm/0.25 μm, H2, 40. C @ 2. min, 6. K/min, 280. C @ 10. min |
Capillary | OV-101 | 801. | Egolf and Jurs, 1993 | 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Capillary | CP-Sil 5 | 775. | Damste, van Dalen, et al., 1988 | 25. m/0.32 mm/0.45 μm, Helium, 0. C @ 5. min, 3. K/min; Tend: 300. C |
Capillary | CP-Sil 5 | 775. | Damste, van Dalen, et al., 1988 | 25. m/0.32 mm/0.45 μm, Helium, 0. C @ 5. min, 3. K/min; Tend: 300. C |
Capillary | CP-Sil 5 | 778. | Damste, van Dalen, et al., 1988 | 25. m/0.32 mm/0.45 μm, Helium, 0. C @ 5. min, 3. K/min; Tend: 300. C |
Capillary | CP Sil 5 CB | 775. | Damste, Kock-van Dalen, et al., 1988 | 25. m/0.32 mm/0.45 μm, He, 3. K/min; Tstart: 50. C; Tend: 300. C |
Capillary | CP Sil 5 CB | 775. | Damste, Kock-van Dalen, et al., 1988 | 25. m/0.32 mm/0.45 μm, He, 3. K/min; Tstart: 50. C; Tend: 300. C |
Capillary | CP Sil 5 CB | 778. | Damste, Kock-van Dalen, et al., 1988 | 25. m/0.32 mm/0.45 μm, He, 3. K/min; Tstart: 50. C; Tend: 300. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 787. | Farkas, Héberger, et al., 2004 | Program: not specified |
Capillary | SE-30 | 801. | Vinogradov, 2004 | Program: not specified |
Capillary | PONA | 782. | Yang, Wang, et al., 2003 | 50. m/0.20 mm/0.50 μm; Program: not specified |
Capillary | SE-30 | 800. | P'yanova, Zvereva, et al., 1987 | Column length: 25. m; Column diameter: 0.25 mm; Program: not specified |
Capillary | SE-52 | 815. | van Langenhove and Schamp, 1986 | Column length: 100. m; Column diameter: 0.50 mm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-20M | 1107. | Blazevic and Mastelic, 2008 | 50. m/0.25 mm/0.25 μm, Helium, 70. C @ 4. min, 4. K/min; Tend: 180. C |
Capillary | DB-Wax | 1109. | Umano, Hagi, et al., 1995 | He, 40. C @ 2. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C |
Capillary | Carbowax 20M | 1130. | Egolf and Jurs, 1993 | 2. K/min; Column length: 80. m; Column diameter: 0.2 mm; Tstart: 70. C; Tend: 170. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1130. | Vinogradov, 2004 | Program: not specified |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy 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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