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Dibenzothiophene

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 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
Deltafgas51.0 ± 0.2kcal/molCmChirico, Knipmeyer, et al., 1991ALS
Deltafgas45.2 ± 1.1kcal/molCcrSabbah and Antipine, 1987see Sabbah, 1979; ALS
Deltafgas49.09kcal/molN/AGood, 1972Value computed using «DELTA»fHsolid° value of 120.3±1.5 kj/mol from Good, 1972 and «DELTA»subH° 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, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 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
Deltafsolid24.9 ± 1.1kcal/molCcrSabbah and Antipine, 1987see Sabbah, 1979; ALS
Deltafsolid28.76 ± 0.35kcal/molCcrGood, 1972ALS
Quantity Value Units Method Reference Comment
Deltacsolid-1570.7 ± 1.1kcal/molCcrSabbah and Antipine, 1987see Sabbah, 1979; ALS
Deltacsolid-1574.49 ± 0.32kcal/molCcrGood, 1972ALS
Quantity Value Units Method Reference Comment
solid,1 bar48.805cal/mol*KN/AChirico, Knipmeyer, et al., 1991DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
47.395298.15Chirico, Knipmeyer, et al., 1991T = 5 to 800 K.; DH
46.51298.15O'Rourke and Mraw, 1983T = 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, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 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
Tboil605.7KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus372. ± 1.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple371.820KN/AChirico, Knipmeyer, et al., 1991, 2Uncertainty assigned by TRC = 0.002 K; TRC
Quantity Value Units Method Reference Comment
Deltavap18.7 ± 0.26kcal/molGCHaftka, Parsons, et al., 2006Based on data from 413. - 473. K.; AC
Quantity Value Units Method Reference Comment
Deltasub21. ± 2.kcal/molAVGN/AAverage of 6 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
426.20.004Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
15.7388.N/ADykyj, Svoboda, et al., 1999Based on data from 373. - 424. K.; AC
15.2439.N/ADykyj, Svoboda, et al., 1999Based on data from 424. - 608. K.; AC
16.6 ± 0.07380.N/ASteele, Chirico, et al., 1995AC
16.0 ± 0.07420.N/ASteele, Chirico, et al., 1995AC
15.4 ± 0.07460.N/ASteele, Chirico, et al., 1995AC
14.8 ± 0.07500.N/ASteele, Chirico, et al., 1995AC
14.2 ± 0.07540.N/ASteele, Chirico, et al., 1995AC
13.6 ± 0.07580.N/ASteele, Chirico, et al., 1995AC
12.9 ± 0.07620.N/ASteele, Chirico, et al., 1995AC
16.3 ± 0.02400.EB,IPChirico, Knipmeyer, et al., 1991Based on data from 375. - 662. K.; AC
15.5 ± 0.02450.EB,IPChirico, Knipmeyer, et al., 1991Based on data from 375. - 662. K.; AC
14.8 ± 0.02500.EB,IPChirico, Knipmeyer, et al., 1991Based on data from 375. - 662. K.; AC
14.0 ± 0.02550.EB,IPChirico, Knipmeyer, et al., 1991Based on data from 375. - 662. K.; AC
13.2 ± 0.07600.EB,IPChirico, Knipmeyer, et al., 1991Based on data from 375. - 662. K.; AC
12.4 ± 0.1650.EB,IPChirico, Knipmeyer, et al., 1991Based on data from 375. - 662. K.; AC
14.4400.AStephenson and Malanowski, 1987Based on data from 385. - 574. K.; AC
13.6590.CMraw and Keweshan, 1984AC
13.2610.CMraw and Keweshan, 1984AC
12.8630.CMraw and Keweshan, 1984AC
16.6385.GSEdwards and Prausnitz, 1981Based on data from 373. - 403. K.; AC

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
21.8325.THansen and Eckert, 1986Based on data from 303. - 348. K.; AC
21.7348.GSEdwards and Prausnitz, 1981Based on data from 333. - 363. K.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
5.1883371.821N/AChirico, Knipmeyer, et al., 1991DH
5.1577371.0N/AO'Rourke and Mraw, 1983DH
5.16371.8DSCLisicki and Jamróz, 2000AC
5.158371.N/ADomalski and Hearing, 1996AC
5.16373.2N/AO'Rourke and Mraw, 1983AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
13.95371.821Chirico, Knipmeyer, et al., 1991DH
13.90371.0O'Rourke and Mraw, 1983DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 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

View reactions leading to C12H8S+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.44EITerlouw, Heerma, et al., 1974LLK
8.34EIAloisi and Pignataro, 1973LLK
8.23CTSAloisi and Pignataro, 1973LLK
7.90 ± 0.03PIPotapov, Kardash, et al., 1972LLK
8.14CTSMukherjee, 1969RDSH
7.93PERuscic, Kovac, et al., 1978Vertical value; LLK
8.01PEJohnstone and Mellon, 1973Vertical value; LLK

IR Spectrum

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

Gas Phase Spectrum

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IR spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

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

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible 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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Mass spectrum
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Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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 by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Werner, 1949
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 592
Instrument Beckman Spectrophotometer
Melting point 99.5
Boiling point 332.5

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Terlouw, Heerma, et al., 1974
Terlouw, J.K.; Heerma, W.; Frintrop, P.C.M.; Dijkstra, G.; Meinema, H.A., Electron-impact induced fragmentation of some heterocyclic-tin compounds, J. Organomet. Chem., 1974, 64, 205. [all data]

Aloisi and Pignataro, 1973
Aloisi, G.G.; Pignataro, S., Molecular complexes of substituted thiophens with «sigma» and «pi» acceptors, J. Chem. Soc. Faraday Trans. 1, 1973, 69, 534. [all data]

Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I., Photoionization of heteroaromatic compounds, Khim. Vys. Energ., 1972, 6, 392. [all data]

Mukherjee, 1969
Mukherjee, T.K., Charge-transfer donor abilities of o,o'bridged biphenyls, J. Phys. Chem., 1969, 73, 3442. [all data]

Ruscic, Kovac, et al., 1978
Ruscic, B.; Kovac, B.; Klasinc, L.; Gusten, H., Photoelectron spectroscopy of J. Heterocycl. Chem.. Fluorene analogues, Z. Naturforsch. A:, 1978, 33, 1006. [all data]

Johnstone and Mellon, 1973
Johnstone, R.A.W.; Mellon, F.A., Photoelectron spectroscopy of sulphur-containing heteroaromatics and molecular orbital calculations, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 1155. [all data]

Werner, 1949
Werner, E.G.G., Synthesis of benzothiophenes, Recl. Trav. Chim. Pays-Bas, 1949, 68, 509-519. [all data]


Notes

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