2,2'-Bithiophene

• Formula: C₈H₆S₂
• Molecular weight: 166.263
• IUPAC Standard InChI: InChI=1S/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H Copy

  
• IUPAC Standard InChIKey: OHZAHWOAMVVGEL-UHFFFAOYSA-N Copy
• CAS Registry Number: 492-97-7
• 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.
• Species with the same structure:
  • a-Thienothiophene
• Other names: 2,2'-Bithienyl; 2,2'-Dithienyl; 2,2'-Dithiophene; Dithienyl
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Options:
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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

Reduced pressure boiling point

Enthalpy of sublimation

Enthalpy of fusion

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 compiled as indicated in comments:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

Electron affinity determinations

Ionization energy determinations

Mass spectrum (electron ionization)

Go To: Top, Phase change data, Gas phase ion energetics data, UV/Visible spectrum, Gas Chromatography, 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

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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Additional Data

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

Normal alkane RI, non-polar column, temperature ramp

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References

Go To: Top, Phase change data, Gas phase ion energetics 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.

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Wynberg and Logothetis, 1956
Wynberg, H.; Logothetis, A., Studies in the Synthesis of Long-chain Compounds, J. Am. Chem. Soc., 1956, 78, 1958. [all data]

Ribeiro da Silva, Santos, et al., 2009
Ribeiro da Silva, Manuel A.V.; Santos, Ana Filipa L.O.M.; Gomes, Jose R.B.; Roux, Maria Victoria; Temprado, Manuel; Jimenez, Pilar; Notario, Rafael, Thermochemistry of Bithiophenes and Thienyl Radicals. A Calorimetric and Computational Study, J. Phys. Chem. A, 2009, 113, 41, 11042-11050, https://doi.org/10.1021/jp905531c . [all data]

Temprado, Roux, et al., 2006
Temprado, Manuel; Roux, Maria Victoria; Jiménez, Pilar; Guzmán-Mejía, Ramón; Juaristi, Eusebio, Thermophysical properties of sulfur heterocycles: Thiane and thiophene derivatives, Thermochimica Acta, 2006, 441, 1, 20-26, https://doi.org/10.1016/j.tca.2005.11.024 . [all data]

Siegert, Vogeler, et al., 2011
Siegert, S.; Vogeler, F.; Marian, C.M.; Weinkauf, R., Throwing light on dark states of alpha-oligothiophenes of chain lengths 2 to 6: radical anion photoelectron spectroscopy and excited-state theory, Phys. Chem. Chem. Phys., 2011, 13, 21, 10350-10363, https://doi.org/10.1039/c0cp02712j . [all data]

Schiedt, Knott, et al., 2000
Schiedt, J.; Knott, W.J.; Le Barbu, K.; Schlag, E.W.; Weinkauf, R., Microsolvation of similar-sized aromatic molecules: Photoelectron spectroscopy of bithiophene-, azulene-, and naphthalene-water anion clusters, J. Chem. Phys., 2000, 113, 21, 9470-9478, https://doi.org/10.1063/1.1319874 . [all data]

Kraak and Wynberg, 1968
Kraak, A.; Wynberg, H., Charge-transfer interaction of dithienyls and cyclopentadithiophenes with 1,3,5-trinitrobenzene (TNB), Tetrahedron, 1968, 24, 3881. [all data]

Sease and Zechmeister, 1947
Sease, J.W.; Zechmeister, L., J. Am. Chem. Soc., 1947, 69, 270. [all data]

Rapior, Konska, et al., 2000
Rapior, S.; Konska, G.; Guillot, J.; Andary, C.; Bessiere, J.-M., Volatile composition of Laetiporus sulphureus, Cryptogamie, Mycol., 2000, 21, 1, 67-72, https://doi.org/10.1016/S0181-1584(00)00109-3 . [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  EA	Electron affinity
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

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