1,4-Butanedithiol

• Formula: C₄H₁₀S₂
• Molecular weight: 122.252
• IUPAC Standard InChI: InChI=1S/C4H10S2/c5-3-1-2-4-6/h5-6H,1-4H2 Copy

  
• IUPAC Standard InChIKey: SMTOKHQOVJRXLK-UHFFFAOYSA-N Copy
• CAS Registry Number: 1191-08-8
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Tetramethylenedithiol; 1,4-Dimercaptobutane; Tetramethylene dimercaptan; butane-1,4-dithiol
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • IR Spectrum
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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

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

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Enthalpy of vaporization

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 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

C₄H₉S₂^- +  =

By formula: C₄H₉S₂^- + H⁺ = C₄H₁₀S₂

 +  = 2 + 

By formula: C₄H₁₀S₂ + I₂ = 2HI + C₄H₈S₂

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 by: John E. Bartmess

De-protonation reactions

C₄H₉S₂^- +  =

By formula: C₄H₉S₂^- + H⁺ = C₄H₁₀S₂

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

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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Kovats' RI, non-polar column, custom temperature program

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Kovats' RI, polar column, isothermal

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Kovats' RI, polar column, custom temperature program

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References

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

Mansson and Sunner, 1962
Mansson, M.; Sunner, S., Heats of combustion and formation of the n-Alkane-αω-dithiols from ethane through pentane, Acta Chem. Scand., 1962, 16, 1863-1869. [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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

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]

Karty, Wu, et al., 2001
Karty, J.M.; Wu, Y.S.; Brauman, J.I., The RS-center dot HSR hydrogen bond: Acidities of alpha,omega- dithiols and electron affinities of their monoradicals, J. Am. Chem. Soc., 2001, 123, 40, 9800-9805, https://doi.org/10.1021/ja0039684 . [all data]

Sunner, 1955
Sunner, S., Strain in 6,8-thioctic acid, Nature (London), 1955, 176, 217. [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]

Möckel and Zolg, 1977
Möckel, H.J.; Zolg, M., Retentionsindices n-aliphatischer Schwefelverbindungen, Z. Anal. Chem., 1977, 285, 1, 45-46, https://doi.org/10.1007/BF00446017 . [all data]

Zhu, Wang, et al., 2007
Zhu, X.H.; Wang, W.; Schramm, K.-W.; Niu, W., Prediction of the Kova´ ts Retention Indices of Thiols by Use of Quantum Chemical and Physicochemical Descriptors, Chromatographia, 2007, 65, 11-12, 719-724, https://doi.org/10.1365/s10337-007-0237-3 . [all data]

Notes

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• Symbols used in this document:
  

  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
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction 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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