Thiophene, tetrahydro-

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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)

Quantity Value Units Method Reference Comment
IE (evaluated)8.38eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)202.9kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity195.8kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.38PIPECOButler and Baer, 1983LBLHLM
8.62 ± 0.05EIDistefano, Foffani, et al., 1971LLK
8.62EIDistefano, Foffani, et al., 1971, 2LLK
8.57 ± 0.15EIGallegos and Kiser, 1962RDSH
8.40PESchmidt and Schweig, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHS+11.0 ± 0.1C3H7PIButler and Baer, 1982T = 298K; LBLHLM
CHS+11.1 ± 0.1C3H7PIButler and Baer, 1982T = 0K; LBLHLM
CHS+13.8 ± 0.2?EIGallegos and Kiser, 1962RDSH
CH2S+10.5C3H6PIPECOButler and Baer, 1983LBLHLM
CH2S+13.0 ± 0.2?EIGallegos and Kiser, 1962RDSH
CH3S+11.1C3H5PIPECOButler and Baer, 1983LBLHLM
CH3S+14.0 ± 0.2?EIGallegos and Kiser, 1962RDSH
C2H2S+17.0 ± 0.3?EIGallegos and Kiser, 1962RDSH
C2H3+18.0 ± 0.4?EIGallegos and Kiser, 1962RDSH
C2H3S+10.36C2H5PIPECOButler and Baer, 1983LBLHLM
C2H3S+15.7 ± 0.4?EIGallegos and Kiser, 1962RDSH
C2H4S+11.7 ± 0.3?EIGallegos and Kiser, 1962RDSH
C3H3+17.2 ± 0.2?EIGallegos and Kiser, 1962RDSH
C3H5+15.5 ± 0.2?EIGallegos and Kiser, 1962RDSH
C4H6+11.9 ± 0.2?EIGallegos and Kiser, 1962RDSH
C4H7+12.4 ± 0.2SHEIGallegos and Kiser, 1962RDSH
C4H7S+10.1HPIPECOButler and Baer, 1983LBLHLM
C4H7S+12.4 ± 0.3HEIGallegos and Kiser, 1962RDSH
C4H8S+10.21C2H4PIPECOButler and Baer, 1983LBLHLM

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+ + Thiophene, tetrahydro- = (C4H8S+ • Thiophene, tetrahydro-)

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

Quantity Value Units Method Reference Comment
Δr16.9kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; ΔrH<

(C4H8S+ • Thiophene, tetrahydro-) + Thiophene, tetrahydro- = (C4H8S+ • 2Thiophene, tetrahydro-)

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

Quantity Value Units Method Reference Comment
Δr7.8kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Δr18.cal/mol*KN/AHiraoka, Takimoto, et al., 1987gas phase; Entropy change calculated or estimated

C4H9S+ + Thiophene, tetrahydro- = (C4H9S+ • Thiophene, tetrahydro-)

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

Quantity Value Units Method Reference Comment
Δr16.9kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase
Quantity Value Units Method Reference Comment
Δr21.0cal/mol*KPHPMSHiraoka, Takimoto, et al., 1987gas phase

(C4H9S+ • Thiophene, tetrahydro-) + Thiophene, tetrahydro- = (C4H9S+ • 2Thiophene, tetrahydro-)

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

Quantity Value Units Method Reference Comment
Δr7.9kcal/molPHPMSHiraoka, Takimoto, et al., 1987gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Δr18.cal/mol*KN/AHiraoka, Takimoto, et al., 1987gas phase; Entropy change calculated or estimated

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

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
NIST MS number 694

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UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Fehnel and Carmack, 1949
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 10651
Instrument Beckman DU
Melting point - 96.1
Boiling point 121

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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Column type Active phase Temperature (C) I Reference Comment
CapillaryDB-5100.821.0Miller and Bruno, 200330. m/0.25 mm/0.1 μm
CapillaryDB-5120.832.5Miller and Bruno, 200330. m/0.25 mm/0.1 μm
CapillaryDB-560.806.3Miller and Bruno, 200330. m/0.25 mm/0.1 μm
CapillaryDB-580.812.6Miller and Bruno, 200330. m/0.25 mm/0.1 μm
PackedApiezon M130.834.Garbuzov, Misharina, et al., 1985He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m
CapillaryOV-101100.805.Gal'pern, Gollandskikh, et al., 1976H2; Column length: 100. m; Column diameter: 0.25 mm
CapillaryApiezon L120.839.Agr, Tesaric, et al., 1973 
CapillarySqualane120.775.Agr, Tesaric, et al., 1973 
CapillarySqualane86.772.Agr, Tesaric, et al., 1973 
CapillaryApiezon L120.839.Agrawal, Tesarík, et al., 1972N2; Column length: 100. m; Column diameter: 0.3 mm
CapillarySqualane120.775.Agrawal, Tesarík, et al., 1972N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm
CapillarySqualane86.772.Agrawal, Tesarík, et al., 1972N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm

Normal alkane RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryPolydimethyl siloxane with 5 % Ph groups100.821.Safa and Hadjmohannadi, 200530. m/0.25 mm/0.10 μm, Nitrogen
CapillaryPolydimethyl siloxane with 5 % Ph groups60.806.Safa and Hadjmohannadi, 200530. m/0.25 mm/0.10 μm, Nitrogen
CapillaryPolydimethyl siloxane with 5 % Ph groups80.813.Safa and Hadjmohannadi, 200530. m/0.25 mm/0.10 μm, Nitrogen

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-101838.Blazevic and Mastelic, 200825. m/0.20 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min; Tend: 200. C
CapillaryPONA779.Yang, Wang, et al., 200350. m/0.20 mm/0.50 μm, 2. K/min; Tstart: 30. C; Tend: 150. C
CapillaryPONA782.Yang, Yang, et al., 200350. m/0.20 mm/0.50 μm, Helium, 2. K/min; Tstart: 30. C; Tend: 170. C
CapillaryRSL-200802.Jirovetz, Smith, et al., 200230. m/0.25 mm/0.25 μm, H2, 40. C @ 2. min, 6. K/min, 280. C @ 10. min
CapillaryOV-101801.Egolf and Jurs, 19932. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C
CapillaryCP-Sil 5775.Damste, van Dalen, et al., 198825. m/0.32 mm/0.45 μm, Helium, 0. C @ 5. min, 3. K/min; Tend: 300. C
CapillaryCP-Sil 5775.Damste, van Dalen, et al., 198825. m/0.32 mm/0.45 μm, Helium, 0. C @ 5. min, 3. K/min; Tend: 300. C
CapillaryCP-Sil 5778.Damste, van Dalen, et al., 198825. m/0.32 mm/0.45 μm, Helium, 0. C @ 5. min, 3. K/min; Tend: 300. C
CapillaryCP Sil 5 CB775.Damste, Kock-van Dalen, et al., 198825. m/0.32 mm/0.45 μm, He, 3. K/min; Tstart: 50. C; Tend: 300. C
CapillaryCP Sil 5 CB775.Damste, Kock-van Dalen, et al., 198825. m/0.32 mm/0.45 μm, He, 3. K/min; Tstart: 50. C; Tend: 300. C
CapillaryCP Sil 5 CB778.Damste, Kock-van Dalen, et al., 198825. 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

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone787.Farkas, Héberger, et al., 2004Program: not specified
CapillarySE-30801.Vinogradov, 2004Program: not specified
CapillaryPONA782.Yang, Wang, et al., 200350. m/0.20 mm/0.50 μm; Program: not specified
CapillarySE-30800.P'yanova, Zvereva, et al., 1987Column length: 25. m; Column diameter: 0.25 mm; Program: not specified
CapillarySE-52815.van Langenhove and Schamp, 1986Column length: 100. m; Column diameter: 0.50 mm; Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-20M1107.Blazevic and Mastelic, 200850. m/0.25 mm/0.25 μm, Helium, 70. C @ 4. min, 4. K/min; Tend: 180. C
CapillaryDB-Wax1109.Umano, Hagi, et al., 1995He, 40. C @ 2. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C
CapillaryCarbowax 20M1130.Egolf and Jurs, 19932. 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

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M1130.Vinogradov, 2004Program: not specified

References

Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

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]

Fehnel and Carmack, 1949
Fehnel, E.A.; Carmack, M., J. Am. Chem. Soc., 1949, 71, 84. [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, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References