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Benzenethiol

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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
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

References

Go To: Top, 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.

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 «pi» 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]

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]


Notes

Go To: Top, Gas phase ion energetics data, References