Thiophene, tetrahydro-

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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

Quantity Value Units Method Reference Comment
Δfgas-8.02 ± 0.28kcal/molCcrDavies and Sunner, 1962see Sunner, 1963
Δfgas-8.25 ± 0.36kcal/molCcrHubbard, Katz, et al., 1954Heat of combustion calculated author's U=-773.80

Phase change 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil393. ± 3.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus174.35KN/ADavies and Sunner, 1962, 2Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Ttriple176.98KN/AHubbard, Finke, et al., 1952Uncertainty assigned by TRC = 0.06 K; TRC
Quantity Value Units Method Reference Comment
Tc632.KN/AMajer and Svoboda, 1985 
Tc632.KN/ACheng, McCoubrey, et al., 1962Uncertainty assigned by TRC = 1. K; extrapolated to zero time to correct for decompostion calibr. vs NPL thermometer J.C.McCoubrey, A.R.Ubbelohde Trans. Faraday Soc. 1960,56,114; TRC
Quantity Value Units Method Reference Comment
Δvap9.3 ± 0.1kcal/molAVGN/AAverage of 6 values; Individual data points

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
8.284394.3N/AMajer and Svoboda, 1985 
8.87358.A,EBStephenson and Malanowski, 1987Based on data from 343. to 434. K. See also Hubbard, Finke, et al., 1952, 2 and Osborn and Douslin, 1966.; AC
9.01346.EBWhite, Barnard--Smith, et al., 1952Based on data from 331. to 401. K.; AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kcal/mol) β Tc (K) Reference Comment
350. to 394.12.610.2624632.Majer and Svoboda, 1985 

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
333.4 to 373.55.002901979.9812.346Eon, Pommier, et al., 1971Coefficents calculated by NIST from author's data.
344.33 to 433.604.11461401.939-53.543Osborn and Douslin, 1966 

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
1.7572176.98Hubbard, Finke, et al., 1952, 2DH
1.76177.Lange, 1985AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
9.928176.98Hubbard, Finke, et al., 1952, 2DH

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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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Mass spectrum
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Additional Data

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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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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 thermochemistry data, Phase change 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.

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]

Davies and Sunner, 1962, 2
Davies, J.V.; Sunner, S., Heats of Combustion and Formation of Thiolane and the Thiolenes, Acta Chem. Scand., 1962, 16, 1870. [all data]

Hubbard, Finke, et al., 1952
Hubbard, W.N.; Finke, H.L.; Scott, D.W.; McCullough, J.P.; Katz, C.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G., Thiacyclopentyane: Heat Capacity, Heats of Fusion and Vaporization, Vapor Pressure, Entropy, Heat of Formation and Thermo. Functions, J. Am. Chem. Soc., 1952, 74, 6025-30. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Cheng, McCoubrey, et al., 1962
Cheng, D.C.H.; McCoubrey, J.C.; Phillips, D.G., Critical Temperatures of Some Organic Cyclic Compounds, Trans. Faraday Soc., 1962, 58, 224. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Hubbard, Finke, et al., 1952, 2
Hubbard, W.N.; Finke, H.L.; Scott, D.W.; McCullough, J.P.; Katz, C.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G., Thiacyclopentane: heat capacity, heats of fusion and vaporization, vapor pressure, entropy, heat of formation and thermodynamic functions, J. Am. Chem. Soc., 1952, 74, 6025-6030. [all data]

Osborn and Douslin, 1966
Osborn, A.G.; Douslin, D.R., Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum., J. Chem. Eng. Data, 1966, 11, 4, 502-509, https://doi.org/10.1021/je60031a014 . [all data]

White, Barnard--Smith, et al., 1952
White, P.T.; Barnard--Smith, D.G.; Fidler, F.A., Vapor Pressure--Temperature Relationships of Sulfur Compounds Related to Petroleum, Ind. Eng. Chem., 1952, 44, 6, 1430-1438, https://doi.org/10.1021/ie50510a064 . [all data]

Eon, Pommier, et al., 1971
Eon, C.; Pommier, C.; Guiochon, G., Vapor pressures and second virial coefficients of some five-membered heterocyclic derivatives, J. Chem. Eng. Data, 1971, 16, 4, 408-410, https://doi.org/10.1021/je60051a008 . [all data]

Lange, 1985
Lange, N.A., Lange's Handbook of Chemistry, 13th Edition, J.A. Dean, ed(s)., McGraw-Hill, New York, NY, 1985, 1792. [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, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, References