1,3-Propanedithiol
- Formula: C3H8S2
- Molecular weight: 108.226
- IUPAC Standard InChI: InChI=1S/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2
- IUPAC Standard InChIKey: ZJLMKPKYJBQJNH-UHFFFAOYSA-N
- CAS Registry Number: 109-80-8
- 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: Dithiotrimethyleneglycol; Trimethylene dimercaptan; Trimethylenedithioglycol; Trimethylenedithiol; 1,3-Dimercaptopropane; 1,3-Propanedimercaptan; NDR-132; propane-1,3-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 | -29.8 ± 1.2 | kJ/mol | Ccb | Mansson and Sunner, 1962 | hf298_H2SO4.115=-212.24 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -79.5 ± 1.2 | kJ/mol | Ccb | Mansson and Sunner, 1962 | hf298_H2SO4.115=-212.24 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3449.2 ± 1.1 | kJ/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 | 442.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 49.66 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
| ΔvapH° | 49.7 ± 0.1 | kJ/mol | V | Mansson and Sunner, 1962 | hf298_H2SO4.115=-212.24 kcal/mol; ALS |
| ΔvapH° | 49.7 | kJ/mol | N/A | Mansson and Sunner, 1962 | DRB |
| ΔvapH° | 49.7 | kJ/mol | N/A | Mansson and Sunner, 1962 | AC |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 50.9 | 353. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 338. to 446. K.; AC |
| 41.6 | 398. | A | Stephenson and Malanowski, 1987 | Based on data from 377. to 446. K.; 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess
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
+
= 2
+
By formula: C3H8S2 + I2 = 2HI + C3H6S2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -107.7 | kJ/mol | Cm | Sunner, 1955 | liquid phase; solvent: Ethanol/water(90/10); ALS |
C3H7S2- + =
By formula: C3H7S2- + H+ = C3H8S2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrG° | 1429. ± 8.8 | kJ/mol | IMRE | Karty, Wu, et al., 2001 | gas phase; B |
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
C3H7S2- + =
By formula: C3H7S2- + H+ = C3H8S2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrG° | 1429. ± 8.8 | kJ/mol | IMRE | Karty, Wu, et al., 2001 | gas phase |
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
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Apiezon M | 130. | 951. | Garbuzov, Misharina, et al., 1985 | He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m |
| Packed | SE-30 | 110. | 921. | 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 | 951. | 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. | 1448. | 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 | 1457. | Zhu, Wang, et al., 2007 | Program: not specified |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 898. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
| Capillary | DB-5 | 861. | Sinha, Guyer, et al., 1992 | He, 2. K/min; Column length: 30. m; Column diameter: 0.2 mm; Tstart: 30. C; Tend: 200. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 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]
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]
Sunner, 1955
Sunner, S.,
Strain in 6,8-thioctic acid,
Nature (London), 1955, 176, 217. [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]
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]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Sinha, Guyer, et al., 1992
Sinha, N.K.; Guyer, D.E.; Gage, D.A.; Lira, C.T.,
Supercritical carbon dioxide extraction of onion flavors and their analysis by gas chromatography-mass spectrometry,
J. Agric. Food Chem., 1992, 40, 5, 842-845, https://doi.org/10.1021/jf00017a027
. [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, Gas Chromatography, References
- 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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