Benzenemethanethiol
- Formula: C7H8S
- Molecular weight: 124.203
- IUPAC Standard InChIKey: UENWRTRMUIOCKN-UHFFFAOYSA-N
- CAS Registry Number: 100-53-8
- 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: α-Toluenethiol; α-Mercaptotoluene; α-Toluolthiol; (Mercaptomethyl)benzene; Benzyl mercaptan; Benzylthiol; Phenylmethanethiol; Phenylmethyl mercaptan; Thiobenzyl alcohol; α-Tolyl mercaptan; Methanethiol, phenyl-; USAF ex-1509; Benzylhydrosulfide; NSC 41897; toluene-α-thiol
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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 | 93.1 ± 1.1 | kJ/mol | Ccr | Good, 1972 | |
ΔfH°gas | 87.7 ± 2.0 | kJ/mol | Ccr | Mackle and McClean, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = 92. ± 3. kJ/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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 36.5 ± 1.1 | kJ/mol | Ccr | Good, 1972 | |
ΔfH°liquid | 43.9 ± 2.1 | kJ/mol | Ccr | Mackle and McClean, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = 40.0 ± 2.0 kJ/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4536.4 ± 1.0 | kJ/mol | Ccr | Good, 1972 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -4536.0 ± 1.0 kJ/mol |
ΔcH°liquid | -4544.1 ± 2.0 | kJ/mol | Ccr | Mackle and McClean, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -4535.2 ± 2.0 kJ/mol |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 467.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 468. | K | N/A | American Tokyo Kasei, 1988 | BS |
Tboil | 467.15 | K | N/A | Hoffmann, Ess, et al., 1956 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 467. | K | N/A | Zinner, 1953 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 468. | K | N/A | Backer and Dijkstra, 1932 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 56.6 ± 0.2 | kJ/mol | V | Good, 1972 | ALS |
ΔvapH° | 56.6 | kJ/mol | N/A | Good, 1972 | DRB |
ΔvapH° | 56.6 ± 0.1 | kJ/mol | N/A | Good, 1972 | AC |
ΔvapH° | 51. ± 2. | kJ/mol | E | Mackle and McClean, 1962 | ALS |
ΔvapH° | 43.8 | kJ/mol | N/A | Mackle and McClean, 1962 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.5 | 409. | Dykyj, Svoboda, et al., 1999 | Based on data from 394. to 436. K.; AC |
Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.5 | PE | Frost, Herring, et al., 1972 | LLK |
8.85 | PE | Frost, Herring, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H7+ | 12.0 | SH | EI | Gowenlock, Kay, et al., 1963 | RDSH |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-3729 |
NIST MS number | 233945 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Source | Bol'shakov, et al., 1969 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 20102 |
Instrument | unknown |
Boiling point | 194.5 |
Gas Chromatography
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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: 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. | 1104. | Garbuzov, Misharina, et al., 1985 | He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m |
Packed | Apiezon M | 130. | 1104. | Golovnya, Garbuzov, et al., 1978 | Chromosorb W, AW/DMS; Column length: 2.1 m |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1615. | Majcher and Jelen, 2007 | 30. m/0.25 mm/0.25 μm; Program: 40C(2min) => 40C/min => 60C(2min) => 5C/min => 240C |
Capillary | Supelcowax-10 | 1615. | Majcher and Jelén, 2005 | 30. m/0.25 mm/0.25 μm, He; Program: 40C(2min) => 40C/min => 60(2min)C => 5C/min => 240C |
Capillary | DB-FFAP | 1626. | Huynh-Ba, Matthey-Doret, et al., 2003 | 30. m/0.32 mm/0.25 μm; Program: 35C(2min) => 6C/min => 180C => 10C/min => 240C (10min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1080. | Tellez, Khan, et al., 2002 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 240. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 1067. | Vinogradov, 2004 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1631. | Vinogradov, 2004 | Program: not specified |
Capillary | DB-Wax | 1618. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, NIST Subscription Links, 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 McClean, 1962
Mackle, H.; McClean, R.T.B.,
Studies in the thermochemistry of organic sulphides. Part 4.-Heat of formation of the mercaptyl radical,
Trans. Faraday Soc., 1962, 58, 895-899. [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]
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]
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]
American Tokyo Kasei, 1988
American Tokyo Kasei,
TCI American Organic Chemical 88/89 Catalog, American Tokyo Kasei, Portland, OR, 1988, 1610. [all data]
Hoffmann, Ess, et al., 1956
Hoffmann, F.W.; Ess, R.J.; Simmons, T.C.; Hanzel, R.S.,
The Desulfurization of Mercaptans with Trialkyl Phosphites,
J. Am. Chem. Soc., 1956, 78, 6414. [all data]
Zinner, 1953
Zinner, H.,
Perparation of Mercaptans,
Chem. Ber., 1953, 86, 825. [all data]
Backer and Dijkstra, 1932
Backer, H.J.; Dijkstra, N.D.,
The Thioethers of Pentaerythritol,
Recl. Trav. Chim. Pays-Bas, 1932, 51, 289. [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]
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]
Gowenlock, Kay, et al., 1963
Gowenlock, B.G.; Kay, J.; Majer, J.R.,
Electron impact studies of some sulphides and disulphides,
J. Chem. Soc. Faraday Trans., 1963, 59, 2463. [all data]
Bol'shakov, et al., 1969
Bol'shakov, G.F., et al.,
Ultraviolet spectra of heteroorganic compounds, 1969, 95. [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]
Majcher and Jelen, 2007
Majcher, M.A.; Jelen, H.H.,
Effect of Cysteine and Cystine Addition on Sensory Profile and Potent Odorants of Extruded Potato Snacks,
J. Agric. Food Chem., 2007, 55, 14, 5754-5760, https://doi.org/10.1021/jf0703147
. [all data]
Majcher and Jelén, 2005
Majcher, M.A.; Jelén, H.H.,
Identification of potent odorants formed during the preparation of extruded potato snacks,
J. Agric. Food Chem., 2005, 53, 16, 6432-6437, https://doi.org/10.1021/jf050412x
. [all data]
Huynh-Ba, Matthey-Doret, et al., 2003
Huynh-Ba, T.; Matthey-Doret, W.; Fay, L.B.; Rhlid, R.B.,
Generation of thiols by biotransformation of cysteine-aldehyde conjugates with Baker's yeast,
J. Agric. Food Chem., 2003, 51, 12, 3629-3635, https://doi.org/10.1021/jf026198j
. [all data]
Tellez, Khan, et al., 2002
Tellez, M.R.; Khan, I.A.; Kobaisy, M.; Schrader, K.K.; Dayan, F.E.; Osbrink, W.,
Composition of the essential oil of Lepidium meyenii (Walp.),
Phytochemistry, 2002, 61, 2, 149-155, https://doi.org/10.1016/S0031-9422(02)00208-X
. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [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
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- Symbols used in this document:
AE Appearance energy Tboil Boiling point 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 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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