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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Mass spectrum (electron ionization)
  • 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
• Options:
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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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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

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

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 as indicated in comments:
B - John E. Bartmess
M - 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

C₄H₃S^- +  =

By formula: C₄H₃S^- + H⁺ = C₄H₄S

C₄H₄S⁺ +  = (C₄H₄S⁺ • )

By formula: C₄H₄S⁺ + C₄H₄S = (C₄H₄S⁺ • C₄H₄S)

(C₄H₄S⁺ • ) +  = (C₄H₄S⁺ • 2)

By formula: (C₄H₄S⁺ • C₄H₄S) + C₄H₄S = (C₄H₄S⁺ • 2C₄H₄S)

C₄H₅S⁺ +  = (C₄H₅S⁺ • )

By formula: C₄H₅S⁺ + C₄H₄S = (C₄H₅S⁺ • C₄H₄S)

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:
B - John E. Bartmess
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
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C₄H₄S⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₃S^- +  =

By formula: C₄H₃S^- + H⁺ = C₄H₄S

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

C₄H₄S⁺ +  = (C₄H₄S⁺ • )

By formula: C₄H₄S⁺ + C₄H₄S = (C₄H₄S⁺ • C₄H₄S)

(C₄H₄S⁺ • ) +  = (C₄H₄S⁺ • 2)

By formula: (C₄H₄S⁺ • C₄H₄S) + C₄H₄S = (C₄H₄S⁺ • 2C₄H₄S)

C₄H₅S⁺ +  = (C₄H₅S⁺ • )

By formula: C₄H₅S⁺ + C₄H₄S = (C₄H₅S⁺ • C₄H₄S)

IR Spectrum

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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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Notes

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

Zaheeruddin and Lodhi, 1991
Zaheeruddin, M.; Lodhi, Z.H., Enthalpies of formation of some cyclic compounds, Phys. Chem. (Peshawar Pak.), 1991, 10, 111-118. [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]

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]

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 propertie of thiophene, J. Am. Chem. Soc., 1949, 71, 797-808. [all data]

Moore, Renquist, et al., 1940
Moore, G.E.; Renquist, M.L.; Parks, G.S., Thermal data on organic compounds. XX. Modern combustion data for two methylnonanes, methyl ethyl ketone, thiophene and six cycloparaffins, J. Am. Chem. Soc., 1940, 62, 1505-1507. [all data]

Sunner, 1955
Sunner, S., Thermochemical investigations on organic sulfur compounds. V. On the resonance energy of thiolacetic acid, thiourea, thiosemicarbzaide, thiophene and thianthrene, Acta Chem. Scand., 1955, 9, 847-854. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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. Thermodynam., 1985, 17, 949-966. [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, 1513-1517. [all data]

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, 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. Thermodyn., 1985, 17, 10, 949, https://doi.org/10.1016/0021-9614(85)90008-4 . [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 Properties of Thiophene, J. Am. Chem. Soc., 1949, 71, 797. [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, 1513-17. [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]

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., 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]

DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P., Formation and Reactions of Heteroaromatic Anions in the Gas Phase, J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001 . [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]

Klasinc, Sabljic, et al., 1982
Klasinc, L.; Sabljic, A.; Kluge, G.; Rieger, J.; Scholz, M., Chemistry of excited states. Part 13. Assignment of lowest .PI.-ionizations in photoelectron spectra of thiophen, furan, and pyrrole, J. Chem. Soc. Perkin Trans. 2, 1982, 539. [all data]

Galasso, Klasinc, et al., 1981
Galasso, V.; Klasinc, L.; Sabluic, A.; Trinajstic, N.; Pappalardo, G.C.; Steglich, W., Conformation and photoelectron spectra of 2-(2-Furyl)pyrrole and 2-(2-tThienyl)pyrrole, J. Chem. Soc. Perkin Trans. 2, 1981, 127. [all data]

Tedder and Vidaud, 1980
Tedder, J.M.; Vidaud, P.H., Charge exchange mass spectra of thiophene, pyrrole and furan, J. Chem. Soc. Faraday Trans. 2, 1980, 76, 1516. [all data]

Butler and Baer, 1980
Butler, J.J.; Baer, T., Thermochemistry and dissociation dynamics of state-selected C₄H₄X ions. 1. Thiophene, J. Am. Chem. Soc., 1980, 102, 6764. [all data]

Van Veen, 1976
Van Veen, E.H., Triplet π-π^* transitions in thiophene, furan and pyrrole by low-energy electron-impact spectroscopy, Chem. Phys. Lett., 1976, 41, 535. [all data]

Thorstad and Undheim, 1974
Thorstad, O.; Undheim, K., Mass spectrometry of onium compounds. XXIV. Ionisation potential in structure analysis of pyridodiazo-oxides, Chem. Scr., 1974, 6, 222. [all data]

Clark, Gleiter, et al., 1973
Clark, P.A.; Gleiter, R.; Heilbronner, E., Photoelectron spectra of planar sulfur J. Heterocycl. Chem., Tetrahedron, 1973, 29, 3085. [all data]

Aloisi and Pignataro, 1973
Aloisi, G.G.; Pignataro, S., Molecular complexes of substituted thiophens with σ and π acceptors, J. Chem. Soc. Faraday Trans. 1, 1973, 69, 534. [all data]

DiLonardo, Galloni, et al., 1972
DiLonardo, G.; Galloni, G.; Trombetti, A.; Zauli, C., Electronic spectrum of thiophen and some deuterated thiophens, J. Chem. Soc. Faraday Trans., 1972, 68, 2009. [all data]

Linda, Marino, et al., 1971
Linda, P.; Marino, G.; Pignataro, S., A comparison of sensitivities to substituent effects of five- membered heteroaromatic rings in gas phase ionization, J. Chem. Soc. B, 1971, 1585. [all data]

Derrick, Asbrink, et al., 1971
Derrick, P.J.; Asbrink, L.; Edqvist, O.; Lindholm, E., Photoelectron-spectroscopical study of the vibrations of furan, thiophene, pyrrole and cyclopentadiene, Spectrochim. Acta, 1971, 27A, 2525. [all data]

Potapov and Bazhenov, 1970
Potapov, V.K.; Bazhenov, B.A., The photionization of pyrrole, furan, and thiophene, High Energy Chem., 1970, 505, In original 553. [all data]

Baker, Betteridge, et al., 1970
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E., Application of photoelectron spectrometry to pesticide analysis. Photoelectron spectra of fivemembered heterocycles and related molecules, Anal. Chem., 1970, 42, 1064. [all data]

Eland, 1969
Eland, J.H.D., Photoelectron spectra of conjugated hydrocarbons and heteromolecules, Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Price and Walsh, 1941
Price, W.C.; Walsh, A.D., The absorption spectra of the cyclic dienes in the vacuum ultra-violet, Proc. Roy. Soc. (London), 1941, A179, 201. [all data]

Bajic, Humski, et al., 1985
Bajic, M.; Humski, K.; Klasinc, L.; Ruscic, B., Substitution effects on electronic structure of thiophene, Z. Naturforsch. B:, 1985, 40, 1214. [all data]

Bock and Roth, 1983
Bock, H.; Roth, B., Radical ions. 49. Redox reactions of some thiophene derivatives, Phosphorus Sulfur, 1983, 14, 211. [all data]

Mellink and Janssen, 1978
Mellink, W.A.; Janssen, M.J., Photoelectron spectra of aromatic sulphides and sulphones, J. Chem. Res. Synop., 1978, 422. [all data]

Bozic, Humski, et al., 1977
Bozic, Z.; Humski, K.; Cvitas, T.; Klasinc, L., Photoelectron spectra of bromo- and iodo- thiophens, J. Chem. Soc. Perkin Trans. 2, 1977, 1413. [all data]

Schafer, Schweig, et al., 1973
Schafer, W.; Schweig, A.; Gronowitz, S.; Taticchi, A.; Fringuelli, F., Reversal in the sequence of two highest occupied molecular orbitals in the series thiophen, selenophen, and tellurophen, J. Chem. Soc. Chem. Commun., 1973, 541. [all data]

Khvostenko, 1962
Khvostenko, V.I., Ionisation of thiophen and some of its derivatives by electron impact, Zh. Fiz. Khim., 1962, 36, 384, In original 197. [all data]

Stepanov, Perov, et al., 1988
Stepanov, A.N.; Perov, A.A.; Kabanov, S.P.; Simonov, A.P., Formation of long-lived, highly excited atoms during dissociative excitation of CH₃CN, CH₃CH₂OH, CH₃COOH, HCOOH, and C₄H₄S molecules on electron impact, Russ. J. Phys. Chem., 1988, 22, 81. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  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
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  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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