Disulfide, dimethyl

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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
Δfgas-24.1 ± 2.3kJ/molCcbVoronkov, Klyuchnikov, et al., 1989 
Δfgas-24.kJ/molIonHawari, Griller, et al., 1986 
Δfgas-24.1 ± 0.84kJ/molCcbHubbard, Douslin, et al., 1958 

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
Δfliquid-62.6 ± 2.0kJ/molCcbVoronkov, Klyuchnikov, et al., 1989ALS
Δfliquid-62.47 ± 0.84kJ/molCcbHubbard, Douslin, et al., 1958ALS
Quantity Value Units Method Reference Comment
Δcliquid-2786.5 ± 0.71kJ/molCcbHubbard, Douslin, et al., 1958Reanalyzed by Cox and Pilcher, 1970, Original value = -2784.2 ± 0.71 kJ/mol; ALS
Quantity Value Units Method Reference Comment
liquid235.39J/mol*KN/AScott, Finke, et al., 1950DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
146.11298.15Scott, Finke, et al., 1950T = 13 to 352 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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil382.9KN/AWeast and Grasselli, 1989BS
Tboil382.9KN/AMajer and Svoboda, 1985 
Tboil381.15KN/APryor and Platt, 1963Uncertainty assigned by TRC = 1.5 K; TRC
Tboil383.KN/AMcallan, Cullum, et al., 1951Uncertainty assigned by TRC = 1.5 K; TRC
Tboil0.KN/ATrotter and Thompson, 1946TRC
Quantity Value Units Method Reference Comment
Tfus188.5KN/AMcallan, Cullum, et al., 1951Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Ttriple188.44KN/AScott, Finke, et al., 1950, 2Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc615.0KN/AAnselme and Teja, 1990Uncertainty assigned by TRC = 50. K; Tc > 615 K, which was observed with decomposition; TRC
Tc605.7KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Δvap38.2 ± 0.6kJ/molAVGN/AAverage of 9 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
33.78382.9N/AMajer and Svoboda, 1985 
37.8312.AStephenson and Malanowski, 1987Based on data from 297. to 402. K.; AC
36.0 ± 0.1341.CHubbard, Douslin, et al., 1958AC
34.9 ± 0.1360.CHubbard, Douslin, et al., 1958AC
33.7 ± 0.1383.CHubbard, Douslin, et al., 1958AC
36.7336.EBWhite, Barnard--Smith, et al., 1952Based on data from 321. to 388. K.; AC
36.2349.N/AScott, Finke, et al., 1950Based on data from 334. to 401. K.; AC
38.2303.N/AScott, Finke, et al., 1950Based on data from 288. to 333. K.; AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kJ/mol) β Tc (K) Reference Comment
298. to 383.50.50.2463605.7Majer and Svoboda, 1985 

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 Comment
273. to 333.4.195931397.604-49.163Scott, Finke, et al., 1950Coefficents calculated by NIST from author's data.
334.56 to 401.764.08861337.656-55.267Scott, Finke, et al., 1950Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
9.1927188.44Scott, Finke, et al., 1950DH
9.19188.4Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
48.78188.44Scott, Finke, et al., 1950DH

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, Gas phase ion energetics 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: 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

Diethyl disulfide + Disulfide, dimethyl = 2Methyl ethyl disulfide

By formula: C4H10S2 + C2H6S2 = 2C3H8S2

Quantity Value Units Method Reference Comment
Δr0.0 ± 0.63kJ/molEqkHaraldson, Olander, et al., 1960liquid phase; solvent: Nonpolar solvent

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:
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
B - John E. Bartmess

View reactions leading to C2H6S2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)7.4 ± 0.1eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)815.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity782.8kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Δf(+) ion690. ± 15.kJ/molN/AN/A 
Quantity Value Units Method Reference Comment
ΔfH(+) ion,0K707. ± 15.kJ/molN/AN/A 

Electron affinity determinations

EA (eV) Method Reference Comment
1.75LPESCarles, Lecomte, et al., 2001EA is Vertical Detachment Energy. Adiabtic EA estimated as bound, but only by ca 0.1 eV; B
0.23 ± 0.21IMRBRinden, Maricq, et al., 1989EA: between NO, O2.; B

Ionization energy determinations

IE (eV) Method Reference Comment
8.2 ± 0.2IMBLeeck and Kenttamaa, 1994LL
8.18 ± 0.03PILi, Chiu, et al., 1993LL
7.4 ± 0.3EVALButler, Baer, et al., 1983LBLHLM
8.33 ± 0.02PIPECOButler, Baer, et al., 1983T = 298K; LBLHLM
8.3PEColton and Rabalais, 1974LLK
8.71 ± 0.03PECullen, Frost, et al., 1969RDSH
8.46 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
8.97PEChang, Young, et al., 1986Vertical value; LBLHLM
8.96PEKimura, Katsumata, et al., 1981Vertical value; LLK
8.97PEKobayashi, 1978Vertical value; LLK
8.96PEKimura and Osafune, 1975Vertical value; LLK
9.PEGuimon, Guimon, et al., 1975Vertical value; LLK
8.97PEWagner and Bock, 1974Vertical value; LLK
8.98PEBaker, Brisk, et al., 1974Vertical value; LLK
8.82PEKroto and Suffolk, 1972Vertical value; LLK
8.97PEBock, Wagner, et al., 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHS+13.43 ± 0.09?EICullen, Frost, et al., 1970RDSH
CH2S+10.61 ± 0.11?EICullen, Frost, et al., 1970RDSH
CH3+12.9?EICullen, Frost, et al., 1970RDSH
CH3S+10.4 ± 0.1CH3SPIPECOButler, Baer, et al., 1983T = 298K; LBLHLM
CH3S+11.1 ± 0.1?EIPalmer and Lossing, 1962RDSH
CH3S2+10.15 ± 0.10CH3PIPECOButler, Baer, et al., 1983T = 298K; LBLHLM
CH3S2+11.45CH3EIGowenlock, Kay, et al., 1963RDSH
CH3S2+[CH2SSH+]11.07CH3PIMa, Liao, et al., 1994LL
CH3SH+10.4 ± 0.1CH2SPIPECOButler, Baer, et al., 1983T = 298K; LBLHLM
CH4S+9.72 ± 0.09?EICullen, Frost, et al., 1970RDSH
CH3SH2+10.5 ± 0.1CHSPIPECOButler, Baer, et al., 1983T = 298K; LBLHLM
CH5S+11.44 ± 0.15?EICullen, Frost, et al., 1970RDSH
CS+12.0 ± 0.3H2S+CH4EIGal'perin, Bogolyubov, et al., 1969RDSH
C2H2S+10.15 ± 0.08CH3SHPIPECOButler, Baer, et al., 1983T = 298K; LBLHLM
C2H3+14.6 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C2H4+15.6 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
C2H5S+10.08 ± 0.08SHPIPECOButler, Baer, et al., 1983T = 298K; LBLHLM
C2H5S+10.0?EIAmos, Gillis, et al., 1969RDSH
S+15.0 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
S2+15.01 ± 0.13?EICullen, Frost, et al., 1970RDSH
S2+15.9 ± 0.3?EIGal'perin, Bogolyubov, et al., 1969RDSH
S2+15.4 ± 0.3?EIHobrock and Kiser, 1962RDSH

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Voronkov, Klyuchnikov, et al., 1989
Voronkov, M.G.; Klyuchnikov, V.A.; Kolabin, S.N.; Shvets, G.N.; Varusin, P.I.; Deryagina, E.N.; Korchevin, N.A.; Tsvetnitskaya, S.I., Thermochemical properties of diorganyl chalcogenides and dichalcogenides RMnR(M = S, Se, Te; n = 1, 2)., Dokl. Phys. Chem. (Engl. Transl.), 1989, 307, 650-653, In original 1139. [all data]

Hawari, Griller, et al., 1986
Hawari, J.A.; Griller, D.; Lossing, F.P., Thermochemistry of perthiyl radicals, J. Am. Chem. Soc., 1986, 108, 3273-3275. [all data]

Hubbard, Douslin, et al., 1958
Hubbard, W.N.; Douslin, D.R.; McCullough, J.P.; Scott, D.W.; Todd, S.S.; Messerly, J.F.; Hossenlopp, I.A.; George, A.; Waddington, G., 2,3-dithiabutane, 3,4-dithiahexane and 4,5-dithiaoctane: Chemical thermodynamic properties from 0 to 1000°K, J. Am. Chem. Soc., 1958, 80, 3547-3554. [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]

Scott, Finke, et al., 1950
Scott, D.W.; Finke, H.L.; Gross, M.E.; Guthrie, G.B.; Huffman, H.M., 2,3-Dithiabutane: low temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure, entropy and thermodynamic functions, J. Am. Chem. Soc., 1950, 72, 2424-2430. [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]

Pryor and Platt, 1963
Pryor, W.A.; Platt, P.K., Reaction of radicals V. Reaction of Phenyl Radicals with Aliphatic Disulfides, J. Am. Chem. Soc., 1963, 85, 1496. [all data]

Mcallan, Cullum, et al., 1951
Mcallan, D.T.; Cullum, T.V.; Dean, R.A.; Fidler, F.A., The Preparation and Properties of Sulfur Compounds Related to Petroleum I. The Dialkyl Sulfides and Disulfides, J. Am. Chem. Soc., 1951, 73, 3627-32. [all data]

Trotter and Thompson, 1946
Trotter, I.F.; Thompson, H.W., Infrared SPectra of Thiols, Sulfides, and Disulfides, J. Chem. Soc., 1946, 1946, 481. [all data]

Scott, Finke, et al., 1950, 2
Scott, D.W.; Finke, H.L.; Gross, M.E.; Guthrie, G.B.; Huffman, H.M., 2,3-Dithiabutane: Low Temperature Heat Capacity, Heat of Fusion, Heat of Vaporization, Vapor Pressure, Entropy and Thermodynamic Functions, J. Am. Chem. Soc., 1950, 72, 2424-30. [all data]

Anselme and Teja, 1990
Anselme, M.J.; Teja, A.S., The critical properties of rapidly reacting substances, AIChE Symp. Ser., 1990, 86, 279, 128-32. [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]

White, Barnard--Smith, et al., 1952
White, P.T.; Barnard--Smith, D.G.; Fidler, F.A., Vapor Pressure--Temperature Relationships of Sulfur Compounds Related to Petroleum, Ind. Eng. Chem., 1952, 44, 6, 1430-1438, https://doi.org/10.1021/ie50510a064 . [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]

Haraldson, Olander, et al., 1960
Haraldson, L.; Olander, C.J.; Sunner, S.; Varde, K., Equilibrium studies on the disproportionation reaction between some dialkyl disulfides, Acta Chem. Scand., 1960, 14, 1509-1514. [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]

Carles, Lecomte, et al., 2001
Carles, S.; Lecomte, F.; Schermann, J.P.; Desfrancois, C.; Xu, S.; Nilles, J.M.; Bowen, K.H.; Berges, J.; Houe, Nondissociative electron capture by disulfide bonds, J. Phys. Chem. A, 2001, 105, 23, 5622-5626, https://doi.org/10.1021/jp0040603 . [all data]

Rinden, Maricq, et al., 1989
Rinden, E.; Maricq, M.M.; Grabowski, J.J., Gas-Phase Ion-Molecule Reactions of the Nitric Oxide Anion, J. Am. Chem. Soc., 1989, 111, 4, 1203, https://doi.org/10.1021/ja00186a006 . [all data]

Leeck and Kenttamaa, 1994
Leeck, D.T.; Kenttamaa, H.I., Heat of formation of the radical cation of dimethyl disulfide, Org. Mass Spectrom., 1994, 29, 106. [all data]

Li, Chiu, et al., 1993
Li, W.-K.; Chiu, S.-W.; Ma, Z.-X.; Liao, C.L.; Ng, C.Y., Adiabatic ionization energy of CH3SSCH3, J. Chem. Phys., 1993, 99, 8440. [all data]

Butler, Baer, et al., 1983
Butler, J.J.; Baer, T.; Evans, S.A., Jr., Energetics and structures of organosulfur ions: CH3SSCH3+, CH3SS+, C2H5S+, and CH2SH+, J. Am. Chem. Soc., 1983, 105, 3451. [all data]

Colton and Rabalais, 1974
Colton, R.J.; Rabalais, J.W., Photoelectron electronic absorption spectra of SCl2, S2Cl2, S2Br2 and (CH3)2S2, J. Electron Spectrosc. Relat. Phenom., 1974, 3, 345. [all data]

Cullen, Frost, et al., 1969
Cullen, W.R.; Frost, D.C.; Vroom, D.A., Ionization potentials of some sulfur compounds, Inorg. Chem., 1969, 8, 1803. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Chang, Young, et al., 1986
Chang, F.C.; Young, V.Y.; Prather, J.W.; Cheng, K.L., Study of methyl chalcogen compounds with ultraviolet photoelectron spectroscopy, J. Electron Spectrosc. Relat. Phenom., 1986, 40, 363. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Kobayashi, 1978
Kobayashi, T., A new rule for photoelectron angular distributions of molecules, Phys. Lett. A, 1978, 69, 31. [all data]

Kimura and Osafune, 1975
Kimura, K.; Osafune, K., Photoelectron spectroscopic study of skew compounds. III. N,N'-dimethylhydrazine, dimethyl peroxide, and dimethyl disulfide, Bull. Chem. Soc. Jpn., 1975, 48, 2421. [all data]

Guimon, Guimon, et al., 1975
Guimon, M.-F.; Guimon, C.; Pfister-Guillouzo, G., Application of photoelectron spectroscopy to conformational analysis of 1,2,4-trithiolanes, Tetrahedron Lett., 1975, 7, 441. [all data]

Wagner and Bock, 1974
Wagner, G.; Bock, H., Photoelektronenspektren und molekuleigenschaften, XXVI. Die delokalisation von schwefel-elektronenpaaren in alkylsulfiden und -disulfiden, Chem. Ber., 1974, 107, 68. [all data]

Baker, Brisk, et al., 1974
Baker, A.D.; Brisk, M.; Gellender, M., Photoelectron spectra and dihedral angles of disulfides, J. Electron Spectrosc. Relat. Phenom., 1974, 3, 227. [all data]

Kroto and Suffolk, 1972
Kroto, H.W.; Suffolk, R.J., The photoelectron spectrum of an unstable species in the pyrolysis products of dimethyldisulphide, Chem. Phys. Lett., 1972, 15, 545. [all data]

Bock, Wagner, et al., 1972
Bock, H.; Wagner, G.; Kroner, J., Photoelektronenspektren und molekuleigenschaften, XIV. Die delokalisation des schwefel-elektronenpaar in CH3S-substituierten aromaten, Chem. Ber., 1972, 105, 3850. [all data]

Cullen, Frost, et al., 1970
Cullen, W.R.; Frost, D.C.; Pun, M.T., Mass spectra, appearance potentials, heats of formation, and bond energies of some alkyl and perfluoroalkyl sulfides, Inorg. Chem., 1970, 9, 1976. [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]

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]

Ma, Liao, et al., 1994
Ma, Z.-X.; Liao, C.L.; Ng, C.Y.; Cheung, Y.-S.; Li, W.-K.; Baer, T., Experimental and theoretical studies of isomeric CH3S2 and CH3S2+, J. Chem. Phys., 1994, 100, 4870. [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]

Amos, Gillis, et al., 1969
Amos, D.; Gillis, R.G.; Occolowitz, J.L.; Pisani, J.F., The ions [CH3S]+, [C2H5S]+ and [CH3O]+ formed by electron-impact, Org. Mass Spectrom., 1969, 2, 209. [all data]

Hobrock and Kiser, 1962
Hobrock, B.G.; Kiser, R.W., Electron impact spectroscopy of sulfur compounds. I. 2-Thiabutane, 2-thiapentane, and 2,3-dithiabutane, J. Phys. Chem., 1962, 66, 1648. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References