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Benzenethiol

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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas26.86 ± 0.21kcal/molCcrScott, McCullough, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = 26.66 ± 0.28 kcal/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
Deltafliquid15.22 ± 0.20kcal/molCcrScott, McCullough, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = 15.02 ± 0.27 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-928.43 ± 0.15kcal/molCcrScott, McCullough, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = -928.27 ± 0.15 kcal/mol; ALS
Quantity Value Units Method Reference Comment
liquid53.250cal/mol*KN/AScott, McCullough, et al., 1956DH
liquid52.61cal/mol*KN/AParks, Todd, et al., 1936Extrapolation below 90 K, 54.68 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
41.401298.15Scott, McCullough, et al., 1956T = 10 to 380 K.; DH
42.199298.1Parks, Todd, et al., 1936T = 90 to 300 K.; DH

Reaction 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:
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
Deltar340.4 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Deltar>340.1 ± 1.8kcal/molD-EARichardson, Stephenson, et al., 1975gas phase; B
Quantity Value Units Method Reference Comment
Deltar333.4 ± 2.1kcal/molIMREGuillemin, Riague, et al., 2005gas phase; B
Deltar333.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Deltar>333.5 ± 1.9kcal/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-2.97 ± 0.08kcal/molCmWadso, 1960liquid phase; Heat of hydrolysis; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, 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]

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

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