Benzene, (methylthio)-
- Formula: C7H8S
- Molecular weight: 124.203
- IUPAC Standard InChIKey: HNKJADCVZUBCPG-UHFFFAOYSA-N
- CAS Registry Number: 100-68-5
- 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. - Other names: Sulfide, methyl phenyl; (Methylthio)benzene; Anisole, thio-; Methyl phenyl sulfide; Phenyl methyl sulfide; Thioanisol; Thioanisole; 1-Phenyl-1-thiaethane; Methyl phenyl sulphide; (1-Thiaethyl)benzene; Phenylthiomethane; NSC 57916
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Condensed phase thermochemistry data
Go To: Top, 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 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 | 10.35 ± 0.17 | kcal/mol | Ccr | Good, 1972 | ALS |
ΔfH°liquid | 11.47 ± 0.47 | kcal/mol | Ccr | Mackle and Mayrick, 1962 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1085.84 ± 0.86 | kcal/mol | Ccr | Good, 1972 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -1085.73 ± 0.14 kcal/mol; ALS |
ΔcH°liquid | -1086.94 ± 0.47 | kcal/mol | Ccr | Mackle and Mayrick, 1962 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 60.349 | cal/mol*K | N/A | Messerly, Finke, et al., 1974 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
49.240 | 298.15 | Messerly, Finke, et al., 1974 | T = 10 to 330 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 461.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 459. | K | N/A | Pochinok and Limarenko, 1955 | Uncertainty assigned by TRC = 4. K; TRC |
Tboil | 467. | K | N/A | Sabatier and Mailhe, 1910 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 256.44 | K | N/A | Messerly, Finke, et al., 1974, 2 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12.5 ± 0.9 | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.4 | 404. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 389. to 475. K. See also Osborn and Douslin, 1966 and Dykyj, Svoboda, et al., 1999.; AC |
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 |
---|---|---|---|---|
390.30 to 474.77 | 4.13068 | 1603.887 | -79.166 | Osborn and Douslin, 1966 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.54584 | 256.44 | Messerly, Finke, et al., 1974 | DH |
3.549 | 256.4 | Messerly, Finke, et al., 1974 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.83 | 256.44 | Messerly, Finke, et al., 1974 | DH |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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: John E. Bartmess
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
C7H7S- + =
By formula: C7H7S- + H+ = C7H8S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 386.3 ± 5.1 | kcal/mol | G+TS | Ingemann and Nibbering, 1985 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 379.0 ± 5.0 | kcal/mol | IMRB | Ingemann and Nibbering, 1985 | gas phase; value altered from reference due to change in acidity scale |
C7H7S- + =
By formula: C7H7S- + H+ = C7H8S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 381.5 ± 2.1 | kcal/mol | G+TS | Ingemann and Nibbering, 1985 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 374.2 ± 2.0 | kcal/mol | IMRE | Ingemann and Nibbering, 1985 | gas phase; value altered from reference due to change in acidity scale |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Good, 1972
Good, W.D.,
Enthalpies of combustion of 18 organic sulfur compounds related to petroleum,
J. Chem. Eng. Data, 1972, 17, 158-162. [all data]
Mackle and Mayrick, 1962
Mackle, H.; Mayrick, R.G.,
Studies in the thermochemistry of organic sulphides. Part 1.-The gas-phase heats of formation of phenyl methyl, phenyl ethyl, benzyl methyl, and benzyl ethyl sulphides,
Trans. Faraday Soc., 1962, 58, 33-39. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Messerly, Finke, et al., 1974
Messerly, J.F.; Finke, H.L.; Todd, S.S.,
Low-temperature thermal studies on six organo-sulfur compounds,
J. Chem. Thermodynam., 1974, 6, 635-657. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Pochinok and Limarenko, 1955
Pochinok, Ya.; Limarenko, A.P.,
Alkylation of Mercaptans with Alkylaryltriazines,
Ukrain. Khim. Zh., 1955, 21, 628-30. [all data]
Sabatier and Mailhe, 1910
Sabatier, P.; Mailhe, A.,
General Methods for Direct Preparation of Thiols by Catalysic Splitting of Alcohols,
C. R. Hebd. Seances Acad. Sci., 1910, 150, 1217. [all data]
Messerly, Finke, et al., 1974, 2
Messerly, J.F.; Finke, H.L.; Todd, S.S.,
Low-temperature thermal sudies on six organo-sulfur compounds,
J. Chem. Thermodyn., 1974, 6, 635-57. [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]
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]
Ingemann and Nibbering, 1985
Ingemann, S.; Nibbering, N.M.M.,
Gas phase chemistry of alpha-thio carbanions,
Can. J. Chem., 1985, 62, 2273. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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 Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid 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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