Disulfide, dimethyl
- Formula: C2H6S2
- Molecular weight: 94.199
- IUPAC Standard InChIKey: WQOXQRCZOLPYPM-UHFFFAOYSA-N
- CAS Registry Number: 624-92-0
- 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: 2,3-Dithiabutane; Methyl disulfide; (Methyldithio)methane; Dimethyl disulfide; Dimethyl disulphide; (CH3S)2; UN 2381; DMDS; Sulfa-Hitech; NSC 9370; (Methyldisulfanyl)methane
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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 | -24.1 ± 2.3 | kJ/mol | Ccb | Voronkov, Klyuchnikov, et al., 1989 | |
ΔfH°gas | -24. | kJ/mol | Ion | Hawari, Griller, et al., 1986 | |
ΔfH°gas | -24.1 ± 0.84 | kJ/mol | Ccb | Hubbard, Douslin, et al., 1958 |
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: 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
By formula: C4H10S2 + C2H6S2 = 2C3H8S2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.0 ± 0.63 | kJ/mol | Eqk | Haraldson, Olander, et al., 1960 | liquid 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 ± 0.1 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 815.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 782.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°(+) ion | 690. ± 15. | kJ/mol | N/A | N/A | |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH(+) ion,0K | 707. ± 15. | kJ/mol | N/A | N/A |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.75 | LPES | Carles, Lecomte, et al., 2001 | EA is Vertical Detachment Energy. Adiabtic EA estimated as bound, but only by ca 0.1 eV; B |
0.23 ± 0.21 | IMRB | Rinden, Maricq, et al., 1989 | EA: between NO, O2.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.2 ± 0.2 | IMB | Leeck and Kenttamaa, 1994 | LL |
8.18 ± 0.03 | PI | Li, Chiu, et al., 1993 | LL |
7.4 ± 0.3 | EVAL | Butler, Baer, et al., 1983 | LBLHLM |
8.33 ± 0.02 | PIPECO | Butler, Baer, et al., 1983 | T = 298K; LBLHLM |
8.3 | PE | Colton and Rabalais, 1974 | LLK |
8.71 ± 0.03 | PE | Cullen, Frost, et al., 1969 | RDSH |
8.46 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.97 | PE | Chang, Young, et al., 1986 | Vertical value; LBLHLM |
8.96 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
8.97 | PE | Kobayashi, 1978 | Vertical value; LLK |
8.96 | PE | Kimura and Osafune, 1975 | Vertical value; LLK |
9. | PE | Guimon, Guimon, et al., 1975 | Vertical value; LLK |
8.97 | PE | Wagner and Bock, 1974 | Vertical value; LLK |
8.98 | PE | Baker, Brisk, et al., 1974 | Vertical value; LLK |
8.82 | PE | Kroto and Suffolk, 1972 | Vertical value; LLK |
8.97 | PE | Bock, Wagner, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
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 | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 291515 |
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, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Download spectrum in JCAMP-DX format.
Source | missing citation |
---|---|
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. 9109 |
Instrument | Zeiss PMQ II |
Melting point | -85 |
Boiling point | 109.8 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
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, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy ΔfH(+) ion,0K Enthalpy of formation of positive ion at 0K ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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