Benzo[b]thiophene
- Formula: C8H6S
- Molecular weight: 134.198
- IUPAC Standard InChI: InChI=1S/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
- IUPAC Standard InChIKey: FCEHBMOGCRZNNI-UHFFFAOYSA-N
- CAS Registry Number: 95-15-8
- 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: Thianaphthene; Benzothiofuran; Benzothiophen; Thianaphtene; Thianaphthen; Thionaphthene; 1-Benzothiophene; 1-Thiaindene; 2,3-Benzothiophene; Benzothiophene; NSC 47196
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Condensed phase thermochemistry data
Go To: Top, 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 100.60 ± 0.45 | kJ/mol | Cm | Sabbah, 1979 | ALS |
| ΔfH°solid | 100.9 ± 0.92 | kJ/mol | Ccr | Good, 1972 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -4708.21 ± 0.79 | kJ/mol | Ccr | Good, 1972 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 177.11 | J/mol*K | N/A | Finke, Gross, et al., 1954 | DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 172.14 | 295.859 | Chirico, Knipmeyer, et al., 1991 | crystaline, I phase; T = 277 to 495 K. Unsmoothed experimental datum. Cp(liq, 298.15 K, smoothed, graphical extrapolation) = 188.17 J/mol*K.; DH |
| 163.01 | 298.15 | Finke, Gross, et al., 1954 | T = 12 to 335 K.; DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, References, Notes
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:
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 8.17 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.13 ± 0.015 | PE | Gusten, Klasinc, et al., 1976 | LLK |
| 8.73 ± 0.05 | EI | Thorstad and Undheim, 1974 | LLK |
| 8.20 | PE | Clark, Gleiter, et al., 1973 | LLK |
| 8.17 ± 0.05 | PE | Eland, 1969 | RDSH |
References
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sabbah, 1979
Sabbah, R.,
Thermodynamique de substances soufrees. I. Etude thermochimique du benzo-2,3 thiophene et du dibenzothiophene,
Bull. Soc. Chim. France, 1979, 9, 434-437. [all data]
Good, 1972
Good, W.D.,
Enthalpies of combustion of 18 organic sulfur compounds related to petroleum,
J. Chem. Eng. Data, 1972, 17, 158-162. [all data]
Finke, Gross, et al., 1954
Finke, H.L.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Benzothiophene: heat capacity, heat of transition, heat of fusion and entropy. An order-disorder transition,
J. Am. Chem. Soc., 1954, 76, 854-857. [all data]
Chirico, Knipmeyer, et al., 1991
Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Steele, W.V.,
The thermodynamic properties of benzo[b]thiophene,
J. Chem. Thermodyn., 1991, 23, 759-779. [all data]
Gusten, Klasinc, et al., 1976
Gusten, H.; Klasinc, L.; Ruscic, B.,
Photoelectron spectroscopy of J. Heterocycl. Chem.. Indene analogs,
Z. Naturforsch. A:, 1976, 31, 1051. [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]
Eland, 1969
Eland, J.H.D.,
Photoelectron spectra of conjugated hydrocarbons and heteromolecules,
Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid IE (evaluated) Recommended ionization energy S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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