Ethanethiol
- Formula: C2H6S
- Molecular weight: 62.134
- IUPAC Standard InChIKey: DNJIEGIFACGWOD-UHFFFAOYSA-N
- CAS Registry Number: 75-08-1
- 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: Ethyl hydrosulfide; Ethyl mercaptan; Ethyl sulfhydrate; Ethyl thioalcohol; Mercaptoethane; Thioethanol; Thioethyl alcohol; 1-Mercaptoethane; C2H5SH; Aethanethiol; Aethylmercaptan; Etantiolo; Ethaanthiol; Ethylmercaptaan; Ethylmerkaptan; Etilmercaptano; LPG ethyl mercaptan 1010; UN 2363; 1-Ethylthiol; NSC 93877
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Phase change data
Go To: Top, Reaction thermochemistry data, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 309. ± 1. | K | AVG | N/A | Average of 13 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 126.080 | K | N/A | Denyer, Fidler, et al., 1949 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 125.9 | K | N/A | Teets, 1934 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 125.9 | K | N/A | Ellis and Reid, 1932 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 126.15 | K | N/A | Timmermans and Mattaar, 1921 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 125.25 | K | N/A | Finke, McCullough, et al., 1970 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 125.26 | K | N/A | McCullough, Scott, et al., 1952 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 499. | K | N/A | Majer and Svoboda, 1985 | |
Tc | 498.7 | K | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.4 K; by disappearance of meniscus; TRC |
Tc | 498.8 | K | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.4 K; by appearance of turbidity; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 54.90 | bar | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.5066 bar; vapor pressure at Tc; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 4.822 | mol/l | N/A | Berthoud and Brum, 1924 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 27.52 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 27.3 | kJ/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 27.5 | kJ/mol | V | McCullough, Hubbard, et al., 1957 | ALS |
ΔvapH° | 27.5 | kJ/mol | N/A | McCullough, Hubbard, et al., 1957 | DRB |
ΔvapH° | 27.30 ± 0.08 | kJ/mol | V | McCullough, Scott, et al., 1952, 2 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
26.79 | 308.2 | N/A | Majer and Svoboda, 1985 | |
28.4 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 313. K.; AC |
27.5 | 318. | A | Stephenson and Malanowski, 1987 | Based on data from 303. to 375. K.; AC |
26.3 | 380. | A | Stephenson and Malanowski, 1987 | Based on data from 265. to 448. K.; AC |
26.6 | 457. | A | Stephenson and Malanowski, 1987 | Based on data from 442. to 499. K.; AC |
28.4 | 288. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 273. to 339. K. See also McCullough, Scott, et al., 1952, 3 and Osborn and Douslin, 1966.; AC |
28.4 | 288. | N/A | Osborn and Douslin, 1966 | Based on data from 273. to 339. K.; AC |
28.7 | 306. | N/A | Thompson and Linnett, 1935 | AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
281. to 308. | 40.82 | 0.2669 | 499. | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
273.6 to 339.26 | 4.07696 | 1084.531 | -41.765 | Osborn and Douslin, 1966 | |
308. to 493. | 4.44583 | 1330.977 | -8.272 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.975 | 195.26 | McCullough, Scott, et al., 1952, 3 | DH |
4.97 | 195.3 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
25.48 | 195.26 | McCullough, Scott, et al., 1952, 3 | DH |
Reaction thermochemistry data
Go To: Top, Phase change data, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
C2H5S- + =
By formula: C2H5S- + H+ = C2H6S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1488. ± 8.8 | kJ/mol | D-EA | Janousek, Reed, et al., 1980 | gas phase; B |
ΔrH° | 1486. ± 9.2 | kJ/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° | 1460. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: CH6N+ + C2H6S = (CH6N+ • C2H6S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.1 | kJ/mol | PHPMS | Meot-Ner (Mautner) and Sieck, 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 82.0 | J/mol*K | PHPMS | Meot-Ner (Mautner) and Sieck, 1985 | gas phase; M |
By formula: C4H8OS + H2O = C2H4O2 + C2H6S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.0 ± 0.3 | kJ/mol | Cm | Wadso, 1957 | liquid phase; Heat of hydrolysis; ALS |
Gas phase ion energetics data
Go To: Top, Phase change data, Reaction thermochemistry 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 C2H6S+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.31 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 789.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 758.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.28 | PI | Traeger, 1984 | LBLHLM |
9.3 | PE | Ohno, Imai, et al., 1983 | LBLHLM |
9.36 | PE | Kimura, Katsumata, et al., 1981 | LLK |
8.69 | PE | Weiner and Lattman, 1978 | LLK |
9.29 | PE | Ogata, Onizuka, et al., 1973 | LLK |
9.3 ± 0.1 | EI | Keyes and Harrson, 1968 | RDSH |
9.285 ± 0.005 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHS+ | 17.7 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
CH2S+ | 11.2 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
CH3S+ | 11.4 ± 0.1 | CH3 | EI | Keyes and Harrson, 1968 | RDSH |
CS+ | 11.7 ± 0.3 | CH4+H2 | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C2H2+ | 14.7 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C2H3+ | 15.8 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C2H3S+ | 18.3 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C2H4+ | 13.0 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C2H4S+ | 14.0 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C2H5+ | 11.26 | SH | PI | Traeger, 1984 | LBLHLM |
C2H5+ | 12.1 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
C2H5S+ | 11.5 | H | EI | Amos, Gillis, et al., 1969 | RDSH |
H2S+ | 11.8 ± 0.3 | C2H4 | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
H3S+ | 12.41 | ? | EI | Haney and Franklin, 1969 | RDSH |
S+ | 14.2 ± 0.3 | ? | EI | Gal'perin, Bogolyubov, et al., 1969 | RDSH |
De-protonation reactions
C2H5S- + =
By formula: C2H5S- + H+ = C2H6S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1488. ± 8.8 | kJ/mol | D-EA | Janousek, Reed, et al., 1980 | gas phase; B |
ΔrH° | 1486. ± 9.2 | kJ/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° | 1460. ± 8.4 | kJ/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, Reaction thermochemistry 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.
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]
Teets, 1934
Teets, D.E.,
The Relation of the Melting Point to the Number of Carbon Atoms in a Series of Normal Mercaptans,
J. Am. Chem. Soc., 1934, 56, 1143. [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]
Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F.,
Freezing points of orgainic substances VI. New experimental determinations.,
Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]
Finke, McCullough, et al., 1970
Finke, H.L.; McCullough, J.P.; Messerly, J.F.; Guthrie, G.B.; Douslin, D.R.,
Chemical thermodynamic properties for 1-alkanethiols,
J. Chem. Thermodyn., 1970, 2, 27. [all data]
McCullough, Scott, et al., 1952
McCullough, J.P.; Scott, D.W.; Finke, H.L.; Gross, M.E.; Williamson, K.D.; Pennington, R.E.; Waddington, G.; Huffman, H.M.,
Ethanethiol (ethyl mercaptan) thermodynamic properties in the solid, liquid and vapor states thermodynamic functions to 1000k,
J. Am. Chem. Soc., 1952, 74, 2801-4. [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]
Berthoud and Brum, 1924
Berthoud, A.; Brum, R.,
Physical Properties of Some Organic Compounds.,
J. Chim. Phys. Phys.-Chim. Biol., 1924, 21, 143-60. [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]
McCullough, Hubbard, et al., 1957
McCullough, J.P.; Hubbard, W.N.; Frow, F.R.; Hossenlopp, I.A.; Waddington, G.,
Ethanethiol and 2-thiapropane: Heats of formation and isomerization; the chemical thermodynamic properties from 0 to 1000°K,
J. Am. Chem. Soc., 1957, 79, 561-566. [all data]
McCullough, Scott, et al., 1952, 2
McCullough, J.P.; Scott, D.W.; Finke, H.L.; Gross, M.E.; Williamson, K.D.; Pennington, R.E.; Waddington, G.; Huffman, H.M.,
Ethanethiol (ethyl mercaptan): Thermodynamic properties in the solid, liquid and vapor states. Thermodynamic functions to 1000°K,
J. Am. Chem. Soc., 1952, 74, 2801-28. [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., 1952, 3
McCullough, J.P.; Scott, D.W.; Finke, H.L.; Gross, M.E.; Williamson, K.D.; Pennington, R.E.; Waddington, G.; Huffman, H.M.,
Ethanethiol (ethyl mercaptan): thermodynamic properties in the solid, liquid and vapor states. Thermodynamic functions to 1000K,
J. Am. Chem. Soc., 1952, 74, 2801-2804. [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]
Thompson and Linnett, 1935
Thompson, H.W.; Linnett, J.W.,
The vapour pressures of some alkyl sulphides,
Trans. Faraday Soc., 1935, 31, 1743, https://doi.org/10.1039/tf9353101743
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [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]
Janousek, Reed, et al., 1980
Janousek, B.K.; Reed, K.J.; Brauman, J.I.,
Electron photodetachment from mercaptyl anions (RS- electron affinities of mercaptyl radicals and the S-H bond strength in mercaptans),
J. Am. Chem. Soc., 1980, 102, 3125. [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]
Meot-Ner (Mautner) and Sieck, 1985
Meot-Ner (Mautner), M.; Sieck, L.W.,
The Ionic Hydrogen Bond and Ion Solvation. 4. SH+ O and NH+ S Bonds. Correlations with Proton Affinity. Mutual Effects of Weak and Strong Ligands in Mixed Clusters,
J. Phys. Chem., 1985, 89, 24, 5222, https://doi.org/10.1021/j100270a021
. [all data]
Wadso, 1957
Wadso, I.,
The heats of hydrolysis of some alkyl thiolesters,
Acta Chem. Scand., 1957, 11, 1745-1751. [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]
Ohno, Imai, et al., 1983
Ohno, K.; Imai, K.; Matsumoto, S.; Harada, Y.,
Penning ionization electron spectroscopy of C2H5X (X = NH2, OH, H, Cl, I) relative reactivity of orbital localizing on functional groups upon electrophilic attack by metastable helium atoms,
J. Phys. Chem., 1983, 87, 4346. [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]
Weiner and Lattman, 1978
Weiner, M.A.; Lattman, M.,
Ultraviolet photoelectron spectra of some Cr(CO)5L complexes containing organosulfide and organophosphine ligands,
Inorg. Chem., 1978, 17, 1084. [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]
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]
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]
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]
Haney and Franklin, 1969
Haney, M.A.; Franklin, J.L.,
Heats of formation of H3O+, H3S+, and NH4+ by electron impact,
J. Chem. Phys., 1969, 50, 2028. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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