Dibenzothiophene
- Formula: C12H8S
- Molecular weight: 184.257
- IUPAC Standard InChIKey: IYYZUPMFVPLQIF-UHFFFAOYSA-N
- CAS Registry Number: 132-65-0
- 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: [1,1'-Biphenyl]-2,2'-diyl sulfide; Dibenzo[b,d]thiophene; Diphenylene sulfide; 2,2'-Biphenylylene sulfide; 9-Thiafluorene; α-Thiafluorene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, 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
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 213.2 ± 0.7 | kJ/mol | Cm | Chirico, Knipmeyer, et al., 1991 | ALS |
ΔfH°gas | 189.3 ± 4.5 | kJ/mol | Ccr | Sabbah and Antipine, 1987 | see Sabbah, 1979; ALS |
ΔfH°gas | 205.4 | kJ/mol | N/A | Good, 1972 | Value computed using ΔfHsolid° value of 120.3±1.5 kj/mol from Good, 1972 and ΔsubH° value of 85.1 kj/mol from Sabbah and Antipine, 1987.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, IR Spectrum, 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 104.2 ± 4.5 | kJ/mol | Ccr | Sabbah and Antipine, 1987 | see Sabbah, 1979; ALS |
ΔfH°solid | 120.3 ± 1.5 | kJ/mol | Ccr | Good, 1972 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -6571.6 ± 4.4 | kJ/mol | Ccr | Sabbah and Antipine, 1987 | see Sabbah, 1979; ALS |
ΔcH°solid | -6587.7 ± 1.3 | kJ/mol | Ccr | Good, 1972 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 204.20 | J/mol*K | N/A | Chirico, Knipmeyer, et al., 1991 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
198.30 | 298.15 | Chirico, Knipmeyer, et al., 1991 | T = 5 to 800 K.; DH |
194.6 | 298.15 | O'Rourke and Mraw, 1983 | T = 220 to 560 K. Cp = 0.6709 (T/K) - 5.4 (220 to 371.0 K) J/mol*K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, IR Spectrum, 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:
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 | 605.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 372. ± 1. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 371.820 | K | N/A | Chirico, Knipmeyer, et al., 1991, 2 | Uncertainty assigned by TRC = 0.002 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 78.3 ± 1.1 | kJ/mol | GC | Haftka, Parsons, et al., 2006 | Based on data from 413. to 473. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 90. ± 10. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
426.2 | 0.004 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
65.6 | 388. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 373. to 424. K.; AC |
63.4 | 439. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 424. to 608. K.; AC |
69.5 ± 0.3 | 380. | N/A | Steele, Chirico, et al., 1995 | AC |
66.8 ± 0.3 | 420. | N/A | Steele, Chirico, et al., 1995 | AC |
64.3 ± 0.3 | 460. | N/A | Steele, Chirico, et al., 1995 | AC |
61.8 ± 0.3 | 500. | N/A | Steele, Chirico, et al., 1995 | AC |
59.3 ± 0.3 | 540. | N/A | Steele, Chirico, et al., 1995 | AC |
56.8 ± 0.3 | 580. | N/A | Steele, Chirico, et al., 1995 | AC |
54.0 ± 0.3 | 620. | N/A | Steele, Chirico, et al., 1995 | AC |
68.0 ± 0.1 | 400. | EB,IP | Chirico, Knipmeyer, et al., 1991 | Based on data from 375. to 662. K.; AC |
64.9 ± 0.1 | 450. | EB,IP | Chirico, Knipmeyer, et al., 1991 | Based on data from 375. to 662. K.; AC |
61.8 ± 0.1 | 500. | EB,IP | Chirico, Knipmeyer, et al., 1991 | Based on data from 375. to 662. K.; AC |
58.7 ± 0.1 | 550. | EB,IP | Chirico, Knipmeyer, et al., 1991 | Based on data from 375. to 662. K.; AC |
55.4 ± 0.3 | 600. | EB,IP | Chirico, Knipmeyer, et al., 1991 | Based on data from 375. to 662. K.; AC |
51.8 ± 0.4 | 650. | EB,IP | Chirico, Knipmeyer, et al., 1991 | Based on data from 375. to 662. K.; AC |
60.1 | 400. | A | Stephenson and Malanowski, 1987 | Based on data from 385. to 574. K.; AC |
56.9 | 590. | C | Mraw and Keweshan, 1984 | AC |
55.3 | 610. | C | Mraw and Keweshan, 1984 | AC |
53.6 | 630. | C | Mraw and Keweshan, 1984 | AC |
69.4 | 385. | GS | Edwards and Prausnitz, 1981 | Based on data from 373. to 403. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
91.2 | 325. | T | Hansen and Eckert, 1986 | Based on data from 303. to 348. K.; AC |
90.7 | 348. | GS | Edwards and Prausnitz, 1981 | Based on data from 333. to 363. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.708 | 371.821 | N/A | Chirico, Knipmeyer, et al., 1991 | DH |
21.580 | 371.0 | N/A | O'Rourke and Mraw, 1983 | DH |
21.6 | 371.8 | DSC | Lisicki and Jamróz, 2000 | AC |
21.58 | 371. | N/A | Domalski and Hearing, 1996 | AC |
21.6 | 373.2 | N/A | O'Rourke and Mraw, 1983 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58.38 | 371.821 | Chirico, Knipmeyer, et al., 1991 | DH |
58.17 | 371.0 | O'Rourke and Mraw, 1983 | DH |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, 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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Tox21 Consortium/NIST Mass Spectrometry Data Center, 2012 |
NIST MS number | 408598 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, 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.
Chirico, Knipmeyer, et al., 1991
Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Steele, W.V.,
The thermodynamic properties of dibenzothiophene,
J. Chem. Thermodyn., 1991, 23, 431-450. [all data]
Sabbah and Antipine, 1987
Sabbah, R.; Antipine, I.,
Thermodynamic study on four polycycles. Relationship between their energy values and their structure,
Bull. Soc. Chim. Fr., 1987, 392-400. [all data]
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]
O'Rourke and Mraw, 1983
O'Rourke, D.F.; Mraw, S.C.,
Heat capacities and enthalpies of fusion of dibenzothiophene (220 to 560 K) and of biphenyl, cyclohexylbenzene, and cyclohexylcyclohexane (220 to 475 K). Enthalpies and temperatures of three transitions in solid cyclohexylcyclohexane,
J. Chem. Thermodynam., 1983, 15, 489-502. [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]
Chirico, Knipmeyer, et al., 1991, 2
Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Steele, W.V.,
The thermodynamic properties of dibenzothiophene,
J. Chem. Thermodyn., 1991, 23, 431-50. [all data]
Haftka, Parsons, et al., 2006
Haftka, Joris J.H.; Parsons, John R.; Govers, Harrie A.J.,
Supercooled liquid vapour pressures and related thermodynamic properties of polycyclic aromatic hydrocarbons determined by gas chromatography,
Journal of Chromatography A, 2006, 1135, 1, 91-100, https://doi.org/10.1016/j.chroma.2006.09.050
. [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]
Steele, Chirico, et al., 1995
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Nguyen, A.; Knipmeyer, S.E.,
Possible precursors and products of deep hydrodesulfurization of distillate fuels,
The Journal of Chemical Thermodynamics, 1995, 27, 12, 1407-1428, https://doi.org/10.1006/jcht.1995.0149
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Mraw and Keweshan, 1984
Mraw, Stephen C.; Keweshan, Charles F.,
Calvet-type calorimeter for the study of high-temperature processes II. New ballistic method for the enthalpy of vaporization of organic materials at high temperatures,
The Journal of Chemical Thermodynamics, 1984, 16, 9, 873-883, https://doi.org/10.1016/0021-9614(84)90035-1
. [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]
Hansen and Eckert, 1986
Hansen, Philip C.; Eckert, Charles A.,
An improved transpiration method for the measurement of very low vapor pressures,
J. Chem. Eng. Data, 1986, 31, 1, 1-3, https://doi.org/10.1021/je00043a001
. [all data]
Lisicki and Jamróz, 2000
Lisicki, Zygmunt; Jamróz, Malgorzata E.,
(Solid + liquid) equilibria in (polynuclear aromatic+ tertiary amide) systems,
The Journal of Chemical Thermodynamics, 2000, 32, 10, 1335-1353, https://doi.org/10.1006/jcht.2000.0685
. [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, IR Spectrum, Mass spectrum (electron ionization), 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 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 ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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