Benzo[b]thiophene
- Formula: C8H6S
- Molecular weight: 134.198
- 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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 39.74 ± 0.11 | kcal/mol | Cm | Sabbah, 1979 | ALS |
ΔfH°gas | 39.82 | kcal/mol | N/A | Good, 1972 | Value computed using ΔfHsolid° value of 100.9±0.9 kj/mol from Good, 1972 and ΔsubH° value of 65.7 kj/mol from Sabbah, 1979.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change 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 | 24.04 ± 0.11 | kcal/mol | Cm | Sabbah, 1979 | ALS |
ΔfH°solid | 24.11 ± 0.22 | kcal/mol | Ccr | Good, 1972 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1125.29 ± 0.19 | kcal/mol | Ccr | Good, 1972 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 42.330 | cal/mol*K | N/A | Finke, Gross, et al., 1954 | DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.142 | 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 |
38.960 | 298.15 | Finke, Gross, et al., 1954 | T = 12 to 335 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, 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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 494.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 494. to 495. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tboil | 494.15 | K | N/A | Cooper, Crowne, et al., 1967 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 493.1 | K | N/A | Haines, Helm, et al., 1956 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 305. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 304.49 | K | N/A | Haines, Helm, et al., 1956 | Uncertainty assigned by TRC = 0.05 K; determined at U. S. Bureau of Mines, Barltlesville, OK; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 304.48 | K | N/A | Chirico, Knipmeyer, et al., 1991, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 304.50 | K | N/A | Finke, Gross, et al., 1954, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 15.7 ± 0.05 | kcal/mol | C | Sabbah, 1979, 2 | AC |
ΔsubH° | 15.70 ± 0.041 | kcal/mol | C | Sabbah, 1979 | ALS |
ΔsubH° | 15.7 | kcal/mol | N/A | Sabbah, 1979 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
377.2 | 0.026 | Weast and Grasselli, 1989 | BS |
376. to 378. | 0.026 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.5 | 364. | Dykyj, Svoboda, et al., 1999 | Based on data from 349. to 424. K.; AC |
11.4 | 439. | Dykyj, Svoboda, et al., 1999 | Based on data from 424. to 498. K.; AC |
10.8 | 513. | Dykyj, Svoboda, et al., 1999 | Based on data from 498. to 631. K.; AC |
13.0 | 320. | Chirico, Knipmeyer, et al., 1991 | Based on data from 310. to 542. K.; AC |
12.4 | 360. | Chirico, Knipmeyer, et al., 1991 | Based on data from 310. to 542. K.; AC |
11.9 | 400. | Chirico, Knipmeyer, et al., 1991 | Based on data from 310. to 542. K.; AC |
11.0 | 460. | Chirico, Knipmeyer, et al., 1991 | Based on data from 310. to 542. K.; AC |
10.5 | 500. | Chirico, Knipmeyer, et al., 1991 | Based on data from 310. to 542. K.; AC |
9.85 | 540. | Chirico, Knipmeyer, et al., 1991 | Based on data from 310. to 542. K.; AC |
12.9 | 326. | Edwards and Prausnitz, 1981 | Based on data from 306. to 346. K. See also Dykyj, Svoboda, et al., 1999.; AC |
11.3 | 425. | Wieczorek and Kobayashi, 1981 | AC |
10.2 | 505. | Wieczorek and Kobayashi, 1981 | AC |
8.63 | 605. | Wieczorek and Kobayashi, 1981 | AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.8267 | 304.50 | Finke, Gross, et al., 1954 | DH |
2.830 | 304.5 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.283 | 304.50 | Finke, Gross, et al., 1954 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.82483 | 304.48 | crystaline, I | liquid | Chirico, Knipmeyer, et al., 1991 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
9.278 | 304.48 | crystaline, I | liquid | Chirico, Knipmeyer, et al., 1991 | DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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]
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]
Cooper, Crowne, et al., 1967
Cooper, A.R.; Crowne, C.W.P.; Farrell, P.G.,
Gas-Liquid Chromatographic Studies of Electron-Donor-Acceptor Systems,
Trans. Faraday Soc., 1967, 63, 447. [all data]
Haines, Helm, et al., 1956
Haines, W.E.; Helm, R.V.; Cook, G.L.; Ball, J.S.,
Purification and Properties of Organic Sulfur Compounds,
J. Phys. Chem., 1956, 60, 549-55. [all data]
Chirico, Knipmeyer, et al., 1991, 2
Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Steele, W.V.,
The thermodynamic properties of benzo[b]thiophene,
J. Chem. Thermodyn., 1991, 23, 759-79. [all data]
Finke, Gross, et al., 1954, 2
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. [all data]
Sabbah, 1979, 2
Sabbah, R.,
Thermodynamics of sulfur compounds. I. Thermochemical study of 2,3-benzothiophene and dibenzothiophene,
Bull. Soc. Chim. Fr., 1979, 9-10, 434. [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]
Edwards and Prausnitz, 1981
Edwards, D.R.; Prausnitz, J.M.,
Vapor pressures of some sulfur-containing, coal-related compounds,
J. Chem. Eng. Data, 1981, 26, 2, 121-124, https://doi.org/10.1021/je00024a005
. [all data]
Wieczorek and Kobayashi, 1981
Wieczorek, Stefan A.; Kobayashi, Riki,
Vapor-pressure measurements of 1-methylnaphthalene, 2-methylnaphthalene, and 9,10-dihydrophenanthrene at elevated temperatures,
J. Chem. Eng. Data, 1981, 26, 1, 8-11, https://doi.org/10.1021/je00023a005
. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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