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Benzene, (methylthio)-

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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
Deltafgas97.28 ± 0.84kJ/molCcrGood, 1972Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 97.61 ± 0.75 kJ/mol
Deltafgas98. ± 3.kJ/molCcrMackle and Mayrick, 1962 

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
Deltafliquid43.30 ± 0.71kJ/molCcrGood, 1972ALS
Deltafliquid48.0 ± 2.0kJ/molCcrMackle and Mayrick, 1962ALS
Quantity Value Units Method Reference Comment
Deltacliquid-4543.2 ± 3.6kJ/molCcrGood, 1972Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -4542.69 ± 0.59 kJ/mol; ALS
Deltacliquid-4547.8 ± 2.0kJ/molCcrMackle and Mayrick, 1962ALS
Quantity Value Units Method Reference Comment
liquid252.50J/mol*KN/AMesserly, Finke, et al., 1974DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
206.02298.15Messerly, Finke, et al., 1974T = 10 to 330 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, Kenneth Kroenlein 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
Tboil461.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil459.KN/APochinok and Limarenko, 1955Uncertainty assigned by TRC = 4. K; TRC
Tboil467.KN/ASabatier and Mailhe, 1910Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Ttriple256.44KN/AMesserly, Finke, et al., 1974, 2Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Deltavap52. ± 4.kJ/molAVGN/AAverage of 6 values; Individual data points

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
47.5404.A,EBStephenson and Malanowski, 1987Based on data from 389. - 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 (bar)
    T = temperature (K)

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Temperature (K) A B C Reference
390.30 - 474.774.136391603.887-79.166Osborn and Douslin, 1966

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
14.8358256.44Messerly, Finke, et al., 1974DH
14.85256.4Messerly, Finke, et al., 1974AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
57.85256.44Messerly, Finke, et al., 1974DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 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- + Hydrogen cation = Benzene, (methylthio)-

By formula: C7H7S- + H+ = C7H8S

Quantity Value Units Method Reference Comment
Deltar1616. ± 21.kJ/molG+TSIngemann and Nibbering, 1985gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1586. ± 21.kJ/molIMRBIngemann and Nibbering, 1985gas phase; value altered from reference due to change in acidity scale

C7H7S- + Hydrogen cation = Benzene, (methylthio)-

By formula: C7H7S- + H+ = C7H8S

Quantity Value Units Method Reference Comment
Deltar1596. ± 8.8kJ/molG+TSIngemann and Nibbering, 1985gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1566. ± 8.4kJ/molIMREIngemann and Nibbering, 1985gas phase; value altered from reference due to change in acidity scale

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference
4.1 VN/A
4.1 VN/A

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
IE (evaluated)7.94 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)872.6kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity843.7kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.93PEBehan, Johnstone, et al., 1976LLK
7.96 ± 0.01PITrofimov, Mel'der, et al., 1975LLK
8.08CTSAloisi, Santini, et al., 1974LLK
7.92 ± 0.02PIPotapov, Kardash, et al., 1972LLK
7.9 ± 0.15CTSVoigt and Reid, 1964RDSH
8.9EIGowenlock, Kay, et al., 1963RDSH
8.07PETraven', Redchenko, et al., 1981Vertical value; LLK
8.04PEKobayashi, 1978Vertical value; LLK
8.02PESchweig and Thon, 1976Vertical value; LLK
8.60PEDewar, Ernstbrunner, et al., 1974Vertical value; LLK
8.07PEDewar, Ernstbrunner, et al., 1974Vertical value; LLK
8.07PEBock and Wagner, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHS+14.5?EIGowenlock, Kay, et al., 1963RDSH
C6H+14.4?EIGowenlock, Kay, et al., 1963RDSH
C6H5S+12.1 ± 0.1?EIPalmer and Lossing, 1962RDSH
C6H6+12.0?EIGowenlock, Kay, et al., 1963RDSH

De-protonation reactions

C7H7S- + Hydrogen cation = Benzene, (methylthio)-

By formula: C7H7S- + H+ = C7H8S

Quantity Value Units Method Reference Comment
Deltar1616. ± 21.kJ/molG+TSIngemann and Nibbering, 1985gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1586. ± 21.kJ/molIMRBIngemann and Nibbering, 1985gas phase; value altered from reference due to change in acidity scale; B

C7H7S- + Hydrogen cation = Benzene, (methylthio)-

By formula: C7H7S- + H+ = C7H8S

Quantity Value Units Method Reference Comment
Deltar1596. ± 8.8kJ/molG+TSIngemann and Nibbering, 1985gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1566. ± 8.4kJ/molIMREIngemann and Nibbering, 1985gas phase; value altered from reference due to change in acidity scale; B

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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Mass spectrum
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Additional Data

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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-3098
NIST MS number 227860

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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.

Data compiled by: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Braunton, et al., 1972
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. 16364
Instrument Unicam SP 800
Boiling point 76/ 13 mm

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

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Column type Active phase Temperature (C) I Reference Comment
PackedApiezon M130.1106.Garbuzov, Misharina, et al., 1985He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m
PackedApiezon M130.1106.Golovnya, Garbuzov, et al., 1978Chromosorb W, AW/DMS; Column length: 2.1 m
PackedOV-101100.1061.West and Hall, 1975Gas Chrom Q; Column length: 2. m

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryZB-Wax1574.Ledauphin, Saint-Clair, et al., 200430. m/0.25 mm/0.15 «mu»m, He, 35. C @ 5. min, 5. K/min, 220. C @ 10. min

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.1068.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free 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]

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]

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]

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W., An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes, Org. Mass Spectrom., 1976, 11, 207. [all data]

Trofimov, Mel'der, et al., 1975
Trofimov, B.A.; Mel'der, U.K.; Pikver, R.I.; Vyalykh, E.P., Ionization potentials of unsaturated and sulfides the participation of neighboring multiple bonds of heteroatoms in the stabilization of the radical cation, Teor. Eksp. Khim., 1975, 11, 129. [all data]

Aloisi, Santini, et al., 1974
Aloisi, G.G.; Santini, S.; Sorriso, S., Molecular complexes of substituted diphenyl sulphides with «pi» acceptors. Charge transfer spectra and ionization potentials of the donors, J. Chem. Soc. Faraday Trans. 1, 1974, 70, 1908. [all data]

Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I., Photoionization of heteroaromatic compounds, Khim. Vys. Energ., 1972, 6, 392. [all data]

Voigt and Reid, 1964
Voigt, E.M.; Reid, C., Ionization potentials of substituted benzenes and their charge-transfer spectra with tetracyanoethylene, J. Am. Chem. Soc., 1964, 86, 3930. [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]

Traven', Redchenko, et al., 1981
Traven', V.F.; Redchenko, V.V.; Eismont, M.Y.; Stepanov, B.I., Photoelectron spectra and electronic and steric structures of silicon and sulfur-containing analogs of 9,10-dihydroanthracene, J. Gen. Chem. USSR, 1981, 51, 1099, In original 1297. [all data]

Kobayashi, 1978
Kobayashi, T., A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes, Phys. Lett., 1978, 69, 105. [all data]

Schweig and Thon, 1976
Schweig, A.; Thon, N., Measurement of relative conformational stabilities by variable temperature photoelectron spectroscopy. A study of rotational isomerism in thioanisole, Chem. Phys. Lett., 1976, 38, 482. [all data]

Dewar, Ernstbrunner, et al., 1974
Dewar, P.S.; Ernstbrunner, E.; Gilmore, J.R.; Godfrey, M.; Mellor, J.M., Conformational analysis of alkyl aryl ethers and alkyl aryl sulphides by photoelectron spectroscopy, Tetrahedron, 1974, 30, 2455. [all data]

Bock and Wagner, 1972
Bock, H.; Wagner, G., Electron lone pairs in organic sulfides and disulfides, Angew. Chem. Int. Ed. Engl., 1972, 11, 119. [all data]

Palmer and Lossing, 1962
Palmer, T.F.; Lossing, F.P., Free radicals by mass spectrometry. XXVIII. The HS, CH3S, and phenyl-S radicals: ionization potentials and heats of formation, J. Am. Chem. Soc., 1962, 84, 4661. [all data]

Braunton, et al., 1972
Braunton, P.N., et al., J. Chem. Soc., Perkin Trans., 1972, II, 138. [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]

West and Hall, 1975
West, S.D.; Hall, R.C., Substituent contributions to the Kováts retention indices of benzene derivatives, J. Chromatogr. Sci., 1975, 13, 5-11. [all data]

Ledauphin, Saint-Clair, et al., 2004
Ledauphin, J.; Saint-Clair, J.-F.; Lablanquie, O.; Guichard, H.; Founier, N.; Guichard, E.; Barillier, D., Identification of trace volatile compounds in freshly distilled calvados and cognac using preparative separations coupled with gas chromatography-mass spectrometry, J. Agric. Food Chem., 2004, 52, 16, 5124-5134, https://doi.org/10.1021/jf040052y . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References