Benzenethiol

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Gas phase ion energetics data

Go To: Top, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

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

Mass spectrum (electron ionization)

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

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Gas Chromatography

Go To: Top, Gas phase ion energetics data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedApiezon M130.999.Garbuzov, Misharina, et al., 1985He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m
PackedApiezon M130.999.Golovnya, Garbuzov, et al., 1978Chromosorb W, AW/DMS; Column length: 2.1 m
CapillarySqualane120.942.Agrawal, Tesarík, et al., 1972N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm
CapillarySqualane86.933.Agrawal, Tesarík, et al., 1972N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm
CapillaryApiezon L120.966.Agrawal, Tesarík, et al., 1972N2; Column length: 100. m; Column diameter: 0.3 mm

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1491.Peng, Yang, et al., 1991Program: not specified

References

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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 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]

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]

Garbuzov, Misharina, et al., 1985
Garbuzov, V.G.; Misharina, T.A.; Aerov, A.F.; Golovnya, R.V., Gas chromatographic retention indices for sulphur(II)-containing organic substances, J. Anal. Chem. USSR (Engl. Transl.), 1985, 40, 4, 576-586. [all data]

Golovnya, Garbuzov, et al., 1978
Golovnya, R.V.; Garbuzov, V.G.; Aerov, A.F., Gas chromatographic characterization of sulfur-containing compounds. 5. Thiophene, furan, and benzene derivatives, Izv. Akad. Nauk SSSR Ser. Khim., 1978, 11, 2271-2274. [all data]

Agrawal, Tesarík, et al., 1972
Agrawal, B.B.; Tesarík, K.; Janák, J., Gas chromatographic characterization of sulphur compounds in the 93-162° gasoline cut from Romashkino crude oil using Kováts retention indices, J. Chromatogr., 1972, 65, 1, 207-215, https://doi.org/10.1016/S0021-9673(00)86933-2 . [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]


Notes

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References