1,4-Butanedithiol
- Formula: C4H10S2
- Molecular weight: 122.252
- IUPAC Standard InChIKey: SMTOKHQOVJRXLK-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - Other names: Tetramethylenedithiol; 1,4-Dimercaptobutane; Tetramethylene dimercaptan; butane-1,4-dithiol
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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 | -12.08 ± 0.44 | kcal/mol | Ccb | Mansson and Sunner, 1962 | hf298_H2SO4.115=-212.24 kcal/mol |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 468.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 13.2 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 13.22 ± 0.09 | kcal/mol | V | Mansson and Sunner, 1962 | hf298_H2SO4.115=-212.24 kcal/mol; ALS |
ΔvapH° | 13.2 | kcal/mol | N/A | Mansson and Sunner, 1962 | DRB |
ΔvapH° | 13.2 | kcal/mol | N/A | Mansson and Sunner, 1962 | AC |
ΔvapH° | 13.1 | kcal/mol | N/A | Mansson and Sunner, 1962 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
378.7 | 0.039 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.2 | 362. | A | Stephenson and Malanowski, 1987 | Based on data from 347. to 469. K. See also Dykyj, Svoboda, et al., 1999.; AC |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 344.0 ± 2.6 | kcal/mol | G+TS | Karty, Wu, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 341.6 ± 2.1 | kcal/mol | IMRE | Karty, Wu, et al., 2001 | gas phase; B |
By formula: C4H10S2 + I2 = 2HI + C4H8S2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -29.45 | kcal/mol | Cm | Sunner, 1955 | liquid phase; solvent: Ethanol/water(90/10); ALS |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 344.0 ± 2.6 | kcal/mol | G+TS | Karty, Wu, et al., 2001 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 341.6 ± 2.1 | kcal/mol | IMRE | Karty, Wu, et al., 2001 | gas phase |
IR 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
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
View image of digitized spectrum (can be printed in landscape orientation).
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, 1994 |
NIST MS number | 133169 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon M | 130. | 1063. | Garbuzov, Misharina, et al., 1985 | He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m |
Packed | SE-30 | 110. | 1035. | Möckel and Zolg, 1977 | Chromosorb W AW (80-100 mesh); Column length: 2. m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Apiezon M | 1063. | Zhu, Wang, et al., 2007 | Program: not specified |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Carbowax 20M | 110. | 1566. | Möckel and Zolg, 1977 | He, Chromosorb W AW (80-100 mesh); Column length: 6. m |
Kovats' RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | PEG-20M | 1574. | Zhu, Wang, et al., 2007 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
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
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point ΔfH°gas Enthalpy of formation of gas 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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