2,2'-Bithiophene
- Formula: C8H6S2
- Molecular weight: 166.263
- IUPAC Standard InChIKey: OHZAHWOAMVVGEL-UHFFFAOYSA-N
- 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:
- Other names: 2,2'-Bithienyl; 2,2'-Dithienyl; 2,2'-Dithiophene; Dithienyl
- Information on this page:
- Other data available:
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Phase change data
Go To: Top, Gas phase ion energetics data, 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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 533.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 533. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 306. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 305. | K | N/A | Wynberg and Logothetis, 1956 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 20.4 ± 0.1 | kcal/mol | ME | Ribeiro da Silva, Santos, et al., 2009 | Based on data from 275. to 291. K.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
399.7 | 0.016 | Weast and Grasselli, 1989 | BS |
398. to 401. | 0.016 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.6 ± 0.1 | 283. | ME | Ribeiro da Silva, Santos, et al., 2009 | Based on data from 275. to 291. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.94 | 304.2 | Temprado, Roux, et al., 2006 | AC |
Gas phase ion energetics data
Go To: Top, Phase change data, 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 as indicated in comments:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.075 ± 0.020 | LPES | Siegert, Vogeler, et al., 2011 | Neutral triplet state up 2.32 eV; B |
0.0490 ± 0.0080 | LPES | Schiedt, Knott, et al., 2000 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.83 | CTS | Kraak and Wynberg, 1968 | RDSH |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics 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
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 1438. | Rapior, Konska, et al., 2000 | 25. m/0.25 mm/0.13 μm, He, 60. C @ 2. min, 4. K/min; Tend: 200. C |
References
Go To: Top, Phase change data, Gas phase ion energetics data, 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]
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, 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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