Benzenethiol

• Formula: C₆H₆S
• Molecular weight: 110.177
• IUPAC Standard InChI: InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H Copy

  
• IUPAC Standard InChIKey: RMVRSNDYEFQCLF-UHFFFAOYSA-N Copy
• 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:
  • Mercapto-d1-benzene
• Other names: Mercaptobenzene; Phenol, thio-; Phenyl mercaptan; Phenylthiol; Thiophenol; Rcra waste number P014; Thiofenol; UN 2337; USAF XR-19; NSC 6953; 930-69-8
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase ion energetics data

Go To: Top, 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 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)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

 +  =

By formula: C₆H₅S^- + H⁺ = C₆H₆S

Mass spectrum (electron ionization)

Go To: Top, Gas phase ion energetics data, 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

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

Notes

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.