Benzenethiol

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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
Δfgas26.86 ± 0.21kcal/molCcrScott, McCullough, et al., 1956Reanalyzed 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
Δfliquid15.22 ± 0.20kcal/molCcrScott, McCullough, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = 15.02 ± 0.27 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-928.43 ± 0.15kcal/molCcrScott, McCullough, et al., 1956Reanalyzed by Cox and Pilcher, 1970, Original value = -928.27 ± 0.15 kcal/mol; ALS
Quantity Value Units Method Reference Comment
liquid53.250cal/mol*KN/AScott, McCullough, et al., 1956DH
liquid52.61cal/mol*KN/AParks, Todd, et al., 1936Extrapolation below 90 K, 54.68 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
41.401298.15Scott, McCullough, et al., 1956T = 10 to 380 K.; DH
42.199298.1Parks, Todd, et al., 1936T = 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
Tboil441.9KN/AWeast and Grasselli, 1989BS
Tboil442.3KN/AMajer and Svoboda, 1985 
Tboil442.6KN/ABuckingham and Donaghy, 1982BS
Tboil442.25KN/AMorris, Lanum, et al., 1960Uncertainty assigned by TRC = 0.2 K; TRC
Tboil442.7KN/ALecat, 1947Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus258.21KN/AMorris, Lanum, et al., 1960Uncertainty assigned by TRC = 0.02 K; TRC
Tfus258.3KN/AParks, Todd, et al., 1936, 2Uncertainty assigned by TRC = 0.2 K; TRC
Tfus258.25KN/AParks, Todd, et al., 1936, 3Uncertainty assigned by TRC = 0.15 K; TRC
Quantity Value Units Method Reference Comment
Ttriple258.27KN/AScott, McCullough, et al., 1956, 2Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple258.2KN/AParks, Todd, et al., 1936, 3Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc689.5KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Δvap11.37kcal/molN/AMajer and Svoboda, 1985 
Δvap11.6kcal/molN/AScott, McCullough, et al., 1956DRB

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
350.0.039Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
9.543442.3N/AMajer and Svoboda, 1985 
11.0348.N/ADykyj, Svoboda, et al., 1999Based on data from 333. to 471. K.; AC
10.3400.A,EBStephenson and Malanowski, 1987Based on data from 385. to 486. K. See also Osborn and Douslin, 1966 and Scott, McCullough, et al., 1956.; AC
11.64 ± 0.05375.CScott, McCullough, et al., 1956ALS
10.5 ± 0.02375.CScott, McCullough, et al., 1956AC
10.2 ± 0.02395.CScott, McCullough, et al., 1956AC
9.99 ± 0.02407.CScott, McCullough, et al., 1956AC
9.87 ± 0.02417.CScott, McCullough, et al., 1956AC
10.6339.N/Avon Terres, Gebert, et al., 1955Based 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 417.14.770.262689.5Majer 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 485.314.109381529.454-70.102Osborn and Douslin, 1966

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.7359258.27Scott, McCullough, et al., 1956DH
2.744258.2Domalski and Hearing, 1996AC
2.7433258.2Parks, Todd, et al., 1936DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
10.59258.27Scott, McCullough, et al., 1956DH
10.62258.2Parks, Todd, et al., 1936DH

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Δr340.4 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr>340.1 ± 1.8kcal/molD-EARichardson, Stephenson, et al., 1975gas phase; B
Quantity Value Units Method Reference Comment
Δr333.4 ± 2.1kcal/molIMREGuillemin, Riague, et al., 2005gas phase; B
Δr333.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr>333.5 ± 1.9kcal/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

Water + Ethanethioic acid, S-phenyl ester = Benzenethiol + Acetic acid

By formula: H2O + C8H8OS = C6H6S + C2H4O2

Quantity Value Units Method Reference Comment
Δr-2.97 ± 0.08kcal/molCmWadso, 1960liquid phase; Heat of hydrolysis; ALS

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
3.0 VN/A
3.0 VN/A

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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:
L - Sharon G. Lias

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

View reactions leading to C6H6S+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.30 ± 0.01eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
8.3 ± 0.05TRPIFaulk, Dunbar, et al., 1990LL
8.3PEAshby, Enemark, et al., 1988LL
8.3PECarnovale, Kibel, et al., 1982LBLHLM
8.36CTSAloisi, Santini, et al., 1974LLK
9.0 ± 0.1EIHenion and Kingston, 1973LLK
8.28PEFrost, Herring, et al., 1972LLK
8.32 ± 0.01PIMatsunaga, 1961RDSH
8.5PEAshby, Enemark, et al., 1988Vertical value; LL
8.49PECarnovale, Kibel, et al., 1982Vertical value; LBLHLM
8.47PEDewar, Ernstbrunner, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3HS+19.8 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C3H2S+17.0 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C3H3+20.0 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C3H3S+15.5 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C4H2+21.0 ± 0.3?IGal'perin, Bogolyubov, et al., 1969RDSH
C4H2S+17.6 ± 0.3?EIBogolyubov, Plotnikov, et al., 1969RDSH
C4H3+18.0 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C4H4+17.5 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C4H4S+13.2 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C4H4S+[c-C4H4S+]11.5 ± 0.1C2H2TRPIFaulk, Dunbar, et al., 1990LL
C5H3+22.8 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C5H3S+15.1 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C5H5+17.3 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C5H6+12.2 ± 0.1CSEIHenion and Kingston, 1973LLK
C5H6+13.4 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C5H6+[c-C5H6+]11.7 ± 0.1CSTRPIFaulk, Dunbar, et al., 1990LL
C6H3+20.6 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C6H4+17.2 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C6H4S+17.2 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C6H5+14.7 ± 0.3SHEIGal'perin, Bogolyubov, et al., 1969RDSH
C6H5S+11.8 ± 0.1HTRPIFaulk, Dunbar, et al., 1990LL
C6H5S+14.7 ± 0.3HEIGal'perin, Bogolyubov, et al., 1969RDSH
C6H6+14.6 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH

De-protonation reactions

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Δr340.4 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr>340.1 ± 1.8kcal/molD-EARichardson, Stephenson, et al., 1975gas phase; B
Quantity Value Units Method Reference Comment
Δr333.4 ± 2.1kcal/molIMREGuillemin, Riague, et al., 2005gas phase; B
Δr333.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr>333.5 ± 1.9kcal/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

IR Spectrum

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), References, Notes

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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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-3087
NIST MS number 227774

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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, IR Spectrum, Mass spectrum (electron ionization), 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]

Faulk, Dunbar, et al., 1990
Faulk, J.D.; Dunbar, R.C.; Lifshitz, C., Slow Dissociations of thiophenol molecular ion. Study by TRPD and TPIMS, J. Am. Chem. Soc., 1990, 112, 7893. [all data]

Ashby, Enemark, et al., 1988
Ashby, M.T.; Enemark, J.H.; Lichtenberger, D.L., Destabilizing d -p orbital interactions and the alkylation reactions of iron(II)-thiolate complexes, Inorg. Chem., 1988, 27, 191. [all data]

Carnovale, Kibel, et al., 1982
Carnovale, F.; Kibel, M.H.; Nyberg, G.L.; Peel, J.B., Photoelectron spectroscopic assignment of the p-states of benzenethiol, J. Electron Spectrosc. Relat. Phenom., 1982, 25, 171. [all data]

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

Henion and Kingston, 1973
Henion, J.D.; Kingston, D.G.I., Mass spectrometry of organic compounds. VII. Energetics of substituent isomerization in diphenyl sulfide and diphenyl ether, J. Am. Chem. Soc., 1973, 95, 8358. [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]

Matsunaga, 1961
Matsunaga, F.M., Photoionization yield of several molecules in the Schumann region, Contribution No. 27, Hawaii Institute of, 1961, Geophysics, Honolulu. [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]

Gal'perin, Bogolyubov, et al., 1969
Gal'perin, Ya.V.; Bogolyubov, G.M.; Grishin, N.N.; Petrov, A.A., Organic derivatives of elements of groups V and VI. VI. Mass spectra of compounds with S-S bonds, Zh. Obshch. Khim., 1969, 39, 1599, In original 1567. [all data]

Bogolyubov, Plotnikov, et al., 1969
Bogolyubov, G.M.; Plotnikov, V.F.; Boiko, Yu.A.; Petrov, A.A., Organic derivatives of elements of groups V and VI. IX. Mass spectra of vinylacetylene sulfides, Zh. Obshch. Khim., 1969, 39, 2467, In original 2407. [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, IR Spectrum, Mass spectrum (electron ionization), References