Benzenethiol

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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
Δfliquid15.22 ± 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
Δcliquid-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
Δr340.4 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr>340.1 ± 1.8kcal/molD-EARichardson, Stephenson, et al., 1975gas phase; B
Quantity Value Units Method Reference Comment
Δr333.4 ± 2.1kcal/molIMREGuillemin, Riague, et al., 2005gas phase; B
Δr333.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr>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
Δr-2.97 ± 0.08kcal/molCmWadso, 1960liquid phase; Heat of hydrolysis; ALS

Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C6H6S+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.30 ± 0.01eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
8.3 ± 0.05TRPIFaulk, Dunbar, et al., 1990LL
8.3PEAshby, Enemark, et al., 1988LL
8.3PECarnovale, Kibel, et al., 1982LBLHLM
8.36CTSAloisi, Santini, et al., 1974LLK
9.0 ± 0.1EIHenion and Kingston, 1973LLK
8.28PEFrost, Herring, et al., 1972LLK
8.32 ± 0.01PIMatsunaga, 1961RDSH
8.5PEAshby, Enemark, et al., 1988Vertical value; LL
8.49PECarnovale, Kibel, et al., 1982Vertical value; LBLHLM
8.47PEDewar, Ernstbrunner, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3HS+19.8 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C3H2S+17.0 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C3H3+20.0 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C3H3S+15.5 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C4H2+21.0 ± 0.3?IGal'perin, Bogolyubov, et al., 1969RDSH
C4H2S+17.6 ± 0.3?EIBogolyubov, Plotnikov, et al., 1969RDSH
C4H3+18.0 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C4H4+17.5 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C4H4S+13.2 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C4H4S+[c-C4H4S+]11.5 ± 0.1C2H2TRPIFaulk, Dunbar, et al., 1990LL
C5H3+22.8 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C5H3S+15.1 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C5H5+17.3 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C5H6+12.2 ± 0.1CSEIHenion and Kingston, 1973LLK
C5H6+13.4 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C5H6+[c-C5H6+]11.7 ± 0.1CSTRPIFaulk, Dunbar, et al., 1990LL
C6H3+20.6 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C6H4+17.2 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C6H4S+17.2 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C6H5+14.7 ± 0.3SHEIGal'perin, Bogolyubov, et al., 1969RDSH
C6H5S+11.8 ± 0.1HTRPIFaulk, Dunbar, et al., 1990LL
C6H5S+14.7 ± 0.3HEIGal'perin, Bogolyubov, et al., 1969RDSH
C6H6+14.6 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH

De-protonation reactions

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Δr340.4 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr>340.1 ± 1.8kcal/molD-EARichardson, Stephenson, et al., 1975gas phase; B
Quantity Value Units Method Reference Comment
Δr333.4 ± 2.1kcal/molIMREGuillemin, Riague, et al., 2005gas phase; B
Δr333.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr>333.5 ± 1.9kcal/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

References

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

Faulk, Dunbar, et al., 1990
Faulk, J.D.; Dunbar, R.C.; Lifshitz, C., Slow Dissociations of thiophenol molecular ion. Study by TRPD and TPIMS, J. Am. Chem. Soc., 1990, 112, 7893. [all data]

Ashby, Enemark, et al., 1988
Ashby, M.T.; Enemark, J.H.; Lichtenberger, D.L., Destabilizing d -p orbital interactions and the alkylation reactions of iron(II)-thiolate complexes, Inorg. Chem., 1988, 27, 191. [all data]

Carnovale, Kibel, et al., 1982
Carnovale, F.; Kibel, M.H.; Nyberg, G.L.; Peel, J.B., Photoelectron spectroscopic assignment of the p-states of benzenethiol, J. Electron Spectrosc. Relat. Phenom., 1982, 25, 171. [all data]

Aloisi, Santini, et al., 1974
Aloisi, G.G.; Santini, S.; Sorriso, S., Molecular complexes of substituted diphenyl sulphides with π acceptors. Charge transfer spectra and ionization potentials of the donors, J. Chem. Soc. Faraday Trans. 1, 1974, 70, 1908. [all data]

Henion and Kingston, 1973
Henion, J.D.; Kingston, D.G.I., Mass spectrometry of organic compounds. VII. Energetics of substituent isomerization in diphenyl sulfide and diphenyl ether, J. Am. Chem. Soc., 1973, 95, 8358. [all data]

Frost, Herring, et al., 1972
Frost, D.C.; Herring, F.G.; Katrib, A.; McDowell, C.A.; McLean, R.A.N., Photoelectron spectra of CH3SH, (CH3)2S, C6H5SH, and C6H5CH2SH; the bonding between sulfur and carbon, J. Phys. Chem., 1972, 76, 1030. [all data]

Matsunaga, 1961
Matsunaga, F.M., Photoionization yield of several molecules in the Schumann region, Contribution No. 27, Hawaii Institute of, 1961, Geophysics, Honolulu. [all data]

Dewar, Ernstbrunner, et al., 1974
Dewar, P.S.; Ernstbrunner, E.; Gilmore, J.R.; Godfrey, M.; Mellor, J.M., Conformational analysis of alkyl aryl ethers and alkyl aryl sulphides by photoelectron spectroscopy, Tetrahedron, 1974, 30, 2455. [all data]

Gal'perin, Bogolyubov, et al., 1969
Gal'perin, Ya.V.; Bogolyubov, G.M.; Grishin, N.N.; Petrov, A.A., Organic derivatives of elements of groups V and VI. VI. Mass spectra of compounds with S-S bonds, Zh. Obshch. Khim., 1969, 39, 1599, In original 1567. [all data]

Bogolyubov, Plotnikov, et al., 1969
Bogolyubov, G.M.; Plotnikov, V.F.; Boiko, Yu.A.; Petrov, A.A., Organic derivatives of elements of groups V and VI. IX. Mass spectra of vinylacetylene sulfides, Zh. Obshch. Khim., 1969, 39, 2467, In original 2407. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References