2-Propanethiol
- Formula: C3H8S
- Molecular weight: 76.161
- IUPAC Standard InChIKey: KJRCEJOSASVSRA-UHFFFAOYSA-N
- CAS Registry Number: 75-33-2
- 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: Isopropanethiol; Isopropyl mercaptan; Isopropylthiol; 1-Methylethanethiol; 2-Mercaptopropane; 2-Propylmercaptan; iso-C3H7SH; Propanethiol-(2); 2-Propylthiol; NSC 87537; propane-2-thiol
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Phase change data
Go To: Top, 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 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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 328. ± 5. | K | AVG | N/A | Average of 20 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 142.61 | K | N/A | Haines, Helm, et al., 1956 | Uncertainty assigned by TRC = 0.07 K; TRC |
Tfus | 142.61 | K | N/A | Anonymous, 1954 | Uncertainty assigned by TRC = 0.06 K; TRC |
Tfus | 142.52 | K | N/A | Denyer, Fidler, et al., 1949 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 142.5 | K | N/A | Ellis and Reid, 1932 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 142.6300 | K | N/A | McCullough, Finke, et al., 1954 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.08 K; TRC |
Ttriple | 142.6400 | K | N/A | McCullough, Finke, et al., 1954 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.06 K; TRC |
Ttriple | 142.63 | K | N/A | Anonymous, 1951 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 517.3 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.082 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 7.19 | kcal/mol | A,EB | Stephenson and Malanowski, 1987 | Based on data from 283. to 358. K. See also McCullough, Scott, et al., 1954, Osborn and Douslin, 1966, and Hubbard and Waddington, 2010.; AC |
ΔvapH° | 7.05 | kcal/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 7.10 | kcal/mol | N/A | Hubbard and Waddington, 1954 | DRB |
ΔvapH° | 7.038 | kcal/mol | V | McCullough, Finke, et al., 1954, 2 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
6.671 | 325.7 | Majer and Svoboda, 1985 | |
6.6707 | 325.72 | McCullough, Finke, et al., 1954, 3 | P = 101.325 kPa; DH |
7.62 | 257. | Dykyj, Svoboda, et al., 1999 | Based on data from 242. to 348. K.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
290. to 326. | 10.61 | 0.2863 | 517.3 | Majer and Svoboda, 1985 |
Entropy of vaporization
ΔvapS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
20.48 | 325.72 | McCullough, Finke, et al., 1954, 3 | P; DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
283.84 to 358.94 | 3.99653 | 1113.895 | -46.993 | Osborn and Douslin, 1966 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.37 | 142.6 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.11 | 112.5 | Domalski and Hearing, 1996 | CAL |
9.610 | 142.6 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.01263 | 112.5 | crystaline, II | crystaline, I | McCullough, Finke, et al., 1954, 3 | DH |
1.371 | 142.64 | crystaline, I | liquid | McCullough, Finke, et al., 1954, 3 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.11 | 112.5 | crystaline, II | crystaline, I | McCullough, Finke, et al., 1954, 3 | DH |
9.610 | 142.64 | crystaline, I | liquid | McCullough, Finke, et al., 1954, 3 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
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:
B - John E. Bartmess
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
View reactions leading to C3H8S+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.15 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 192.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 184.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.15 | PI | Traeger, 1984 | LBLHLM |
9.14 | PE | Ogata, Onizuka, et al., 1973 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H5S+ | 11.0 ± 0.15 | CH3 | EI | Broer, Weringa, et al., 1979 | LLK |
C2H5S+ | 10.7 ± 0.1 | CH3 | EI | Keyes and Harrson, 1968 | RDSH |
C3H7+ | 10.35 | SH | PI | Traeger, 1984 | LBLHLM |
De-protonation reactions
C3H7S- + =
By formula: C3H7S- + H+ = C3H8S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 353.4 ± 2.2 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 347.1 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Phase change 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.
Haines, Helm, et al., 1956
Haines, W.E.; Helm, R.V.; Cook, G.L.; Ball, J.S.,
Purification and Properties of Organic Sulfur Compounds,
J. Phys. Chem., 1956, 60, 549-55. [all data]
Anonymous, 1954
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 13, Ohio State Univ., 1954. [all data]
Denyer, Fidler, et al., 1949
Denyer, R.L.; Fidler, F.A.; Lowry, R.A.,
Azeotrope Formation Between Thiols and Hydrocarbons,
Ind. Eng. Chem., 1949, 41, 2727-37. [all data]
Ellis and Reid, 1932
Ellis, L.M.; Reid, E.E.,
The Preparation and Properties of A Double Series of Aliphatic Mercaptans,
J. Am. Chem. Soc., 1932, 54, 1674. [all data]
McCullough, Finke, et al., 1954
McCullough, J.P.; Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
2-Propanethiol: Experimental Thermodynamic Studies from 12 to 500 K. The Chemical Thermodynamic Properties from 0 to 1000 K,
J. Am. Chem. Soc., 1954, 76, 4796-802. [all data]
Anonymous, 1951
Anonymous, R.,
, Sunbury Rep. No. 4199, Anglo-Iranian Oil Co., 1951. [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]
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]
McCullough, Scott, et al., 1954
McCullough, J.P.; Scott, D.W.; Pennington, R.E.; Hossenlopp, I.A.; Waddington, Guy,
Nitromethane: The Vapor Heat Capacity, Heat of Vaporization, Vapor Pressure and Gas Imperfection; the Chemical Thermodynamic Properties from 0 to 1500°K.,
J. Am. Chem. Soc., 1954, 76, 19, 4791-4796, https://doi.org/10.1021/ja01648a008
. [all data]
Osborn and Douslin, 1966
Osborn, A.G.; Douslin, D.R.,
Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum.,
J. Chem. Eng. Data, 1966, 11, 4, 502-509, https://doi.org/10.1021/je60031a014
. [all data]
Hubbard and Waddington, 2010
Hubbard, Ward N.; Waddington, Guy,
The heats of combustion, formation and isomerization of propanethiol-1, propane-thiol-2 and 2-thiabutane,
Recl. Trav. Chim. Pays-Bas, 2010, 73, 11, 910-923, https://doi.org/10.1002/recl.19540731107
. [all data]
Reid, 1972
Reid, Robert C.,
Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00,
AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637
. [all data]
Hubbard and Waddington, 1954
Hubbard, W.N.; Waddington, G.,
The heat of combustion, formation and isomerization of propanethiol-1, propane-thiol-2 and 2-thiabutane,
Rec. Trav. Chim. Pays/Bas, 1954, 73, 910. [all data]
McCullough, Finke, et al., 1954, 2
McCullough, J.P.; Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
2-Propanethiol: Experimental thermodynamic studies from 12 to 500°K. The chemical thermodynamic properties from 0 to 1000°K,
J. Am. Chem. Soc., 1954, 76, 4796-48. [all data]
McCullough, Finke, et al., 1954, 3
McCullough, J.P.; Finke, H.L.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
2-Propanethiol: experimental thermodynamic studies from 12 to 500 K. The chemical thermodynamic properties from 0 to 1000 K,
J. Am. Chem. Soc., 1954, 76, 4796-4802. [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]
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]
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]
Traeger, 1984
Traeger, J.C.,
Heat of formation for the SH radical by photoionization mass spectrometry,
Org. Mass Spectrom., 1984, 19, 514. [all data]
Ogata, Onizuka, et al., 1973
Ogata, H.; Onizuka, H.; Nihei, Y.; Kamada, H.,
The photoelectron spectra of alcohols, mercaptans and amines,
Bull. Chem. Soc. Jpn., 1973, 46, 3036. [all data]
Broer, Weringa, et al., 1979
Broer, W.J.; Weringa, W.D.; Nieuwpoort, W.C.,
Rearrangements and fragmentations of [C2H5S]+ ions,
Org. Mass Spectrom., 1979, 14, 543. [all data]
Keyes and Harrson, 1968
Keyes, B.G.; Harrson, A.G.,
The fragmentation of aliphatic sulfur compounds by electron impact,
J. Am. Chem. Soc., 1968, 90, 5671. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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 ΔvapS Entropy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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