Benzenethiol
- Formula: C6H6S
- Molecular weight: 110.177
- IUPAC Standard InChIKey: RMVRSNDYEFQCLF-UHFFFAOYSA-N
- CAS Registry Number: 108-98-5
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Isotopologues:
- Other names: Mercaptobenzene; Phenol, thio-; Phenyl mercaptan; Phenylthiol; Thiophenol; Rcra waste number P014; Thiofenol; UN 2337; USAF XR-19; NSC 6953; 930-69-8
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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 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.3 ± 0.05 | TRPI | Faulk, Dunbar, et al., 1990 | LL |
8.3 | PE | Ashby, Enemark, et al., 1988 | LL |
8.3 | PE | Carnovale, Kibel, et al., 1982 | LBLHLM |
8.36 | CTS | Aloisi, Santini, et al., 1974 | LLK |
9.0 ± 0.1 | EI | Henion and Kingston, 1973 | LLK |
8.28 | PE | Frost, Herring, et al., 1972 | LLK |
8.32 ± 0.01 | PI | Matsunaga, 1961 | RDSH |
8.5 | PE | Ashby, Enemark, et al., 1988 | Vertical value; LL |
8.49 | PE | Carnovale, Kibel, et al., 1982 | Vertical value; LBLHLM |
8.47 | PE | Dewar, Ernstbrunner, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
De-protonation reactions
By formula: C6H5S- + H+ = C6H6S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 340.4 ± 2.1 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
ΔrH° | >340.1 ± 1.8 | kcal/mol | D-EA | Richardson, Stephenson, et al., 1975 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 333.4 ± 2.1 | kcal/mol | IMRE | Guillemin, Riague, et al., 2005 | gas phase; B |
ΔrG° | 333.8 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
ΔrG° | >333.5 ± 1.9 | kcal/mol | H-TS | Richardson, Stephenson, et al., 1975 | gas 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 |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon M | 130. | 999. | Garbuzov, Misharina, et al., 1985 | He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m |
Packed | Apiezon M | 130. | 999. | Golovnya, Garbuzov, et al., 1978 | Chromosorb W, AW/DMS; Column length: 2.1 m |
Capillary | Squalane | 120. | 942. | Agrawal, Tesarík, et al., 1972 | N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm |
Capillary | Squalane | 86. | 933. | Agrawal, Tesarík, et al., 1972 | N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm |
Capillary | Apiezon L | 120. | 966. | Agrawal, Tesarík, et al., 1972 | N2; Column length: 100. m; Column diameter: 0.3 mm |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1491. | Peng, Yang, et al., 1991 | Program: 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
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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