Benzenethiol
- Formula: C6H6S
- Molecular weight: 110.177
- IUPAC Standard InChI: InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
- 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 thermochemistry 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 compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 26.86 ± 0.21 | kcal/mol | Ccr | Scott, McCullough, et al., 1956 | Reanalyzed by Cox and Pilcher, 1970, Original value = 26.66 ± 0.28 kcal/mol |
Reaction thermochemistry 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 compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
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 |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, 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 thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Scott, McCullough, et al., 1956
Scott, D.W.; McCullough, J.P.; Hubbard, W.N.; Messerly, J.F.; Hossenlopp, I.A.; Frow, F.R.; Waddington, G.,
Benzenethiol: Thermodynamic properties in the solid, liquid and vapor states; internal rotation of the thiol group,
J. Am. Chem. Soc., 1956, 78, 5463-5468. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
Wadso, 1960
Wadso, I.,
Heats of hydrolysis of phenyl acetate and phenyl thiolacetate,
Acta Chem. Scand., 1960, 14, 561-565. [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 thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions 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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