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 thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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: 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 |
Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 15.22 ± 0.20 | kcal/mol | Ccr | Scott, McCullough, et al., 1956 | Reanalyzed by Cox and Pilcher, 1970, Original value = 15.02 ± 0.27 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -928.43 ± 0.15 | kcal/mol | Ccr | Scott, McCullough, et al., 1956 | Reanalyzed by Cox and Pilcher, 1970, Original value = -928.27 ± 0.15 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 53.250 | cal/mol*K | N/A | Scott, McCullough, et al., 1956 | DH |
S°liquid | 52.61 | cal/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 54.68 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.401 | 298.15 | Scott, McCullough, et al., 1956 | T = 10 to 380 K.; DH |
42.199 | 298.1 | Parks, Todd, et al., 1936 | T = 90 to 300 K.; DH |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 441.9 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 442.3 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 442.6 | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tboil | 442.25 | K | N/A | Morris, Lanum, et al., 1960 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tboil | 442.7 | K | N/A | Lecat, 1947 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 258.21 | K | N/A | Morris, Lanum, et al., 1960 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 258.3 | K | N/A | Parks, Todd, et al., 1936, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 258.25 | K | N/A | Parks, Todd, et al., 1936, 3 | Uncertainty assigned by TRC = 0.15 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 258.27 | K | N/A | Scott, McCullough, et al., 1956, 2 | Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 258.2 | K | N/A | Parks, Todd, et al., 1936, 3 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 689.5 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.37 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 11.6 | kcal/mol | N/A | Scott, McCullough, et al., 1956 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
350. | 0.039 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.543 | 442.3 | N/A | Majer and Svoboda, 1985 | |
11.0 | 348. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 333. to 471. K.; AC |
10.3 | 400. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 385. to 486. K. See also Osborn and Douslin, 1966 and Scott, McCullough, et al., 1956.; AC |
11.64 ± 0.05 | 375. | C | Scott, McCullough, et al., 1956 | ALS |
10.5 ± 0.02 | 375. | C | Scott, McCullough, et al., 1956 | AC |
10.2 ± 0.02 | 395. | C | Scott, McCullough, et al., 1956 | AC |
9.99 ± 0.02 | 407. | C | Scott, McCullough, et al., 1956 | AC |
9.87 ± 0.02 | 417. | C | Scott, McCullough, et al., 1956 | AC |
10.6 | 339. | N/A | von Terres, Gebert, et al., 1955 | Based on data from 324. to 440. K. See also Boublik, Fried, et al., 1984.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 417. | 14.77 | 0.262 | 689.5 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
387.69 to 485.31 | 4.10938 | 1529.454 | -70.102 | Osborn and Douslin, 1966 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.7359 | 258.27 | Scott, McCullough, et al., 1956 | DH |
2.744 | 258.2 | Domalski and Hearing, 1996 | AC |
2.7433 | 258.2 | Parks, Todd, et al., 1936 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.59 | 258.27 | Scott, McCullough, et al., 1956 | DH |
10.62 | 258.2 | Parks, Todd, et al., 1936 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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 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 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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
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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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]
Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A.,
Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds,
J. Am. Chem. Soc., 1936, 58, 398-401. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Morris, Lanum, et al., 1960
Morris, J.C.; Lanum, W.J.; Helm, R.V.; Haines, W.E.; Cook, G.L.; Ball, J.S.,
Purification and Properties of Ten Organic Sulfur Compounds,
J. Chem. Eng. Data, 1960, 5, 112-6. [all data]
Lecat, 1947
Lecat, M.,
Orthobaric Azeotropes of Sulfides,
Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]
Parks, Todd, et al., 1936, 2
Parks, G.S.; Todd, S.S.; Shomate, C.H.,
Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins,
J. Am. Chem. Soc., 1936, 58, 2505. [all data]
Parks, Todd, et al., 1936, 3
Parks, G.S.; Todd, S.S.; Moore, W.A.,
Thermal Data on Organic Compounds. XVI. Some Heat Capacity, Entropy and Free Energy Data for Typical Benzene Derivatives and Heterocyclic Compounds,
J. Am. Chem. Soc., 1936, 58, 398. [all data]
Scott, McCullough, et al., 1956, 2
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, 5463-8. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Osborn and Douslin, 1966
Osborn, A.G.; Douslin, D.R.,
Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum.,
J. Chem. Eng. Data, 1966, 11, 4, 502-509, https://doi.org/10.1021/je60031a014
. [all data]
von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Brennst.-Chem., 1955, 36, 272. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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