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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Reaction thermochemistry data
Go To: Top, References, Notes
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
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Individual 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 |
By formula: H2O + C8H8OS = C6H6S + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -2.97 ± 0.08 | kcal/mol | Cm | Wadso, 1960 | liquid phase; Heat of hydrolysis; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
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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