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
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• 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:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • 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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Condensed phase thermochemistry data

Go To: Top, Reaction thermochemistry data, Ion clustering data, 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:
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

Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Ion clustering data, 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:
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)

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)

Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering 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

Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, 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.

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]

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]

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]

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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

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]

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]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  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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