Thiophene

• Formula: C₄H₄S
• Molecular weight: 84.140
• IUPAC Standard InChI: InChI=1S/C4H4S/c1-2-4-5-3-1/h1-4H Copy

  
• IUPAC Standard InChIKey: YTPLMLYBLZKORZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-02-1
• 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: Thiacyclopentadiene; CP 34; Furan, thio-; Huile HSO; Huile H50; Thiaphene; Thiofuram; Thiofuran; Thiofurfuran; Thiole; Thiophen; Thiotetrole; Divinylene sulfide; USAF EK-1860; Thiofen; UN 2414; Hopkin's lactic acid reagent; NSC 405073
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• Information on this page:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Phase change data

Go To: Top, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

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

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Enthalpy of sublimation

Enthalpy of fusion

Temperature of phase transition

Enthalpy of phase transition

Entropy of phase transition

IR Spectrum

Go To: Top, Phase change data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

• GAS (50 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: Tanya L. Myers, Russell G. Tonkyn, Ashley M. Oeck, Tyler O. Danby, John S. Loring, Matthew S. Taubman, Stephen W. Sharpe, Jerome C. Birnbaum, and Timothy J. Johnson

• liquid; Bruker Tensor 27 FTIR; 0.4821395 cm^-1 resolution

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

References

Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Notes

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

Goates, Ott, et al., 1973
Goates, J.R.; Ott, J.B.; Reeder, J., Solid + liquid phae equilibria and solid compound formation in hexafluorobenzene + benzene, + pyridine, + furan, and + thiophen, J. Chem. Thermodyn., 1973, 5, 135. [all data]

Timmermans and Hennaut-Roland, 1959
Timmermans, J.; Hennaut-Roland, M., Work of the International Bureau of Physico-Chemical Properties physical constants of twenty organic compounds, J. Chim. Phys. Phys.-Chim. Biol., 1959, 56, 984-1023. [all data]

Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F., Freezing points of orgainic substances VI. New experimental determinations., Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]

Figuiere, Szwarc, et al., 1985
Figuiere, P.; Szwarc, H.; Oguni, M.; Suga, H., Calorimetric study of thiophene from 13 to 300 K. Emergence of two glassy crystalline states, J. Chem. Thermodyn., 1985, 17, 10, 949, https://doi.org/10.1016/0021-9614(85)90008-4 . [all data]

Waddington, Knowlton, et al., 1949
Waddington, G.; Knowlton, J.W.; Scott, D.W.; Oliver, G.D.; Todd, S.S.; Hubbard, W.N.; Smith, J.C.; Huffman, H.M., Thermodynamic Properties of Thiophene, J. Am. Chem. Soc., 1949, 71, 797. [all data]

Jacobs and Parks, 1934
Jacobs, C.J.; Parks, G.S., Thermal data on organic compounds. XIV. Some heat capacity, entropy and free energy data for cyclic substances, J. Am. Chem. Soc., 1934, 56, 1513-17. [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]

Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P., Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds, J. Chem. Eng. Data, 1956, 1, 50. [all data]

Reid, 1972
Reid, Robert C., Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00, AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637 . [all data]

Hubbard, Scott, et al., 1955
Hubbard, W.N.; Scott, D.W.; Frow, F.R.; Waddington, G., Thiophene: Heat of combustion and chemical thermodynamic properties, J. Am. Chem. Soc., 1955, 77, 5855-58. [all data]

Waddington, Knowlton, et al., 1949, 2
Waddington, G.; Knowlton, J.W.; Scott, D.W.; Oliver, G.D.; Todd, S.S.; Hubbard, W.N.; Smith, J.C.; Huffman, H.M., Thermodynamic propertie of thiophene, J. Am. Chem. Soc., 1949, 71, 797-808. [all data]

Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R., Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [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]

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]

Fawcett and Rasmussen, 1945
Fawcett, Frank S.; Rasmussen, Herbert E., Physical Properties of Thiophene ¹, J. Am. Chem. Soc., 1945, 67, 10, 1705-1709, https://doi.org/10.1021/ja01226a026 . [all data]

Milazzo, 1944
Milazzo, G., Gazz. Chim. Ital., 1944, 74, 58. [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]

Milazzo, 1956
Milazzo, G., Ann. Chim. (Rome), 1956, 46, 1105. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Figuiere, Szwarc, et al., 1985, 2
Figuiere, P.; Szwarc, H.; Oguni, M.; Suga, H., Calorimetric study of thiophene from 13 to 300 K. Emergence of two glassy crystalline states, J. Chem. Thermodynam., 1985, 17, 949-966. [all data]

Figuiere, Szwarc, et al., 1984
Figuiere, P.; Szwarc, H.; Oguni, M.; Suga, H., Crystalline thiophene - calorimetric evidence for a glassy crystalline state in both phase sequences, J. Phys., Lett., 1984, 45(24), L1167-L1173. [all data]

Andre, Dworkin, et al., 1982
Andre, D.; Dworkin, A.; Figuiere, P.; Fuchs, A.H.; Szwarc, H., Heat capacity of stable and metastable phases of crystalline thiophene, C. R. Seances Acad. Sci., Ser. 2, 1982, 295, 145-147. [all data]

Jacobs and Parks, 1934, 2
Jacobs, C.J.; Parks, G.S., Thermal data on organic compounds. XIV. Some heat capacity, entropy and free energy data for cyclic substances, J. Am. Chem. Soc., 1934, 56, 1513-1517. [all data]

Notes

Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Ttrs	Temperature of phase transition
  Vc	Critical volume
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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