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Benzenethiol

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas112.4 ± 0.88kJ/molCcrScott, McCullough, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = 111.5 ± 1.2 kJ/mol

Condensed phase thermochemistry data

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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
Deltafliquid63.68 ± 0.84kJ/molCcrScott, McCullough, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = 62.8 ± 1.1 kJ/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3884.6 ± 0.63kJ/molCcrScott, McCullough, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = -3883.9 ± 0.63 kJ/mol; ALS
Quantity Value Units Method Reference Comment
liquid222.80J/mol*KN/AScott, McCullough, et al., 1956DH
liquid220.1J/mol*KN/AParks, Todd, et al., 1936Extrapolation below 90 K, 54.68 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
173.22298.15Scott, McCullough, et al., 1956T = 10 to 380 K.; DH
176.56298.1Parks, Todd, et al., 1936T = 90 to 300 K.; DH

Phase change data

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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, Kenneth Kroenlein director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
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
Tboil441.9KN/AWeast and Grasselli, 1989BS
Tboil442.3KN/AMajer and Svoboda, 1985 
Tboil442.6KN/ABuckingham and Donaghy, 1982BS
Tboil442.25KN/AMorris, Lanum, et al., 1960Uncertainty assigned by TRC = 0.2 K; TRC
Tboil442.7KN/ALecat, 1947Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus258.21KN/AMorris, Lanum, et al., 1960Uncertainty assigned by TRC = 0.02 K; TRC
Tfus258.3KN/AParks, Todd, et al., 1936, 2Uncertainty assigned by TRC = 0.2 K; TRC
Tfus258.25KN/AParks, Todd, et al., 1936, 3Uncertainty assigned by TRC = 0.15 K; TRC
Quantity Value Units Method Reference Comment
Ttriple258.27KN/AScott, McCullough, et al., 1956, 2Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple258.2KN/AParks, Todd, et al., 1936, 3Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc689.5KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Deltavap47.56kJ/molN/AMajer and Svoboda, 1985 
Deltavap48.7kJ/molN/AScott, McCullough, et al., 1956DRB

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
350.0.040Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
39.93442.3N/AMajer and Svoboda, 1985 
45.9348.N/ADykyj, Svoboda, et al., 1999Based on data from 333. - 471. K.; AC
43.1400.A,EBStephenson and Malanowski, 1987Based on data from 385. - 486. K. See also Osborn and Douslin, 1966 and Scott, McCullough, et al., 1956.; AC
48.7 ± 0.2375.CScott, McCullough, et al., 1956ALS
43.8 ± 0.1375.CScott, McCullough, et al., 1956AC
42.6 ± 0.1395.CScott, McCullough, et al., 1956AC
41.8 ± 0.1407.CScott, McCullough, et al., 1956AC
41.3 ± 0.1417.CScott, McCullough, et al., 1956AC
44.3339.N/Avon Terres, Gebert, et al., 1955Based on data from 324. - 440. K. See also Boublik, Fried, et al., 1984.; AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kJ/mol) beta Tc (K) Reference Comment
298. - 417.61.790.262689.5Majer and Svoboda, 1985 

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference
387.69 - 485.314.115091529.454-70.102Osborn and Douslin, 1966

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
11.447258.27Scott, McCullough, et al., 1956DH
11.48258.2Domalski and Hearing, 1996AC
11.478258.2Parks, Todd, et al., 1936DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
44.32258.27Scott, McCullough, et al., 1956DH
44.45258.2Parks, Todd, et al., 1936DH

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:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Deltar1424. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Deltar>1423. ± 7.5kJ/molD-EARichardson, Stephenson, et al., 1975gas phase; B
Quantity Value Units Method Reference Comment
Deltar1395. ± 8.8kJ/molIMREGuillemin, Riague, et al., 2005gas phase; B
Deltar1397. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B
Deltar>1395. ± 7.9kJ/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

Water + Ethanethioic acid, S-phenyl ester = Benzenethiol + Acetic acid

By formula: H2O + C8H8OS = C6H6S + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-12.4 ± 0.3kJ/molCmWadso, 1960liquid phase; Heat of hydrolysis; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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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Mass spectrum
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Additional Data

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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 Japan AIST/NIMC Database- Spectrum MS-NW-3087
NIST MS number 227774

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.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.

Scott, McCullough, et al., 1956
Scott, D.W.; McCullough, J.P.; Hubbard, W.N.; Messerly, J.F.; Hossenlopp, I.A.; Frow, F.R.; Waddington, G., Benzenethiol: Thermodynamic properties in the solid, liquid and vapor states; internal rotation of the thiol group, J. Am. Chem. Soc., 1956, 78, 5463-5468. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A., Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds, J. Am. Chem. Soc., 1936, 58, 398-401. [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]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]

Morris, Lanum, et al., 1960
Morris, J.C.; Lanum, W.J.; Helm, R.V.; Haines, W.E.; Cook, G.L.; Ball, J.S., Purification and Properties of Ten Organic Sulfur Compounds, J. Chem. Eng. Data, 1960, 5, 112-6. [all data]

Lecat, 1947
Lecat, M., Orthobaric Azeotropes of Sulfides, Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]

Parks, Todd, et al., 1936, 2
Parks, G.S.; Todd, S.S.; Shomate, C.H., Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins, J. Am. Chem. Soc., 1936, 58, 2505. [all data]

Parks, Todd, et al., 1936, 3
Parks, G.S.; Todd, S.S.; Moore, W.A., Thermal Data on Organic Compounds. XVI. Some Heat Capacity, Entropy and Free Energy Data for Typical Benzene Derivatives and Heterocyclic Compounds, J. Am. Chem. Soc., 1936, 58, 398. [all data]

Scott, McCullough, et al., 1956, 2
Scott, D.W.; McCullough, J.P.; Hubbard, W.N.; Messerly, J.F.; Hossenlopp, I.A.; Frow, F.R.; Waddington, G., Benzenethiol: Thermodynamic Properties in the Solid, Liquid and Vapor States; Internal Rotation of the Thiol Group, J. Am. Chem. Soc., 1956, 78, 5463-8. [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]

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]

Osborn and Douslin, 1966
Osborn, A.G.; Douslin, D.R., Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum., J. Chem. Eng. Data, 1966, 11, 4, 502-509, https://doi.org/10.1021/je60031a014 . [all data]

von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W., Brennst.-Chem., 1955, 36, 272. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [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]

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005 . [all data]

Richardson, Stephenson, et al., 1975
Richardson, J.H.; Stephenson, L.M.; Brauman, J.I., Photodetachment of electrons from phenoxides and thiophenoxide, J. Am. Chem. Soc., 1975, 97, 2967. [all data]

Guillemin, Riague, et al., 2005
Guillemin, J.C.; Riague, E.H.; Gal, J.F.; Maria, P.C.; Mo, O.; Yanez, M., Acidity trends in alpha,beta-unsaturated sulfur, selenium, and tellurium derivatives: Comparison with C-, Si-, Ge-, Sn-, N-, P-, As-, and Sb-containing analogues, Chem. Eur. J., 2005, 11, 7, 2145-2153, https://doi.org/10.1002/chem.200400989 . [all data]

Wadso, 1960
Wadso, I., Heats of hydrolysis of phenyl acetate and phenyl thiolacetate, Acta Chem. Scand., 1960, 14, 561-565. [all data]


Notes

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