1-Pentanethiol
- Formula: C5H12S
- Molecular weight: 104.214
- IUPAC Standard InChIKey: ZRKMQKLGEQPLNS-UHFFFAOYSA-N
- CAS Registry Number: 110-66-7
- 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: n-Amyl mercaptan; n-Pentyl mercaptan; Amyl hydrosulfide; Amyl mercaptan; Amyl sulfhydrate; Amyl thioalcohol; Pentane-1-thiol; Pentanethiol; Pentyl mercaptan; 1-Mercaptopentane; CH3(CH2)4SH; Mercaptan amylique; Pentalarm; 1-Pentanthiol; 1-Pentylthiol
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -109.7 | kJ/mol | N/A | Sunner, 1963 | Value computed using ΔfHliquid° value of -150.9±0.8 kj/mol from Sunner, 1963 and ΔvapH° value of 41.2 kj/mol from Hubbard, Katz, et al., 1954.; DRB |
ΔfH°gas | -110.8 ± 1.8 | kJ/mol | Ccr | Hubbard, Katz, et al., 1954 | Heat of combustion calculated author's U=-985.05; ALS |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -150.9 ± 0.84 | kJ/mol | Ccr | Sunner, 1963 | correction of Sunner, 1955; ALS |
ΔfH°liquid | -152.0 ± 1.7 | kJ/mol | Ccr | Hubbard, Katz, et al., 1954 | Heat of combustion calculated author's U=-985.05; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4133.8 | kJ/mol | Ccr | Sunner, 1963 | correction of Sunner, 1955; ALS |
ΔcH°liquid | -4132.6 ± 1.5 | kJ/mol | Ccr | Hubbard, Katz, et al., 1954 | Heat of combustion calculated author's U=-985.05; ALS |
ΔcH°liquid | -4151. | kJ/mol | Ccb | Berthelot, 1901 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 310.37 | J/mol*K | N/A | Finke, Scott, et al., 1952 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
201.17 | 296.21 | Finke, Scott, et al., 1952 | T = 12 to 320 K. Value is unsmoothed experimental datum.; DH |
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
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 | 399.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 399. | K | N/A | American Tokyo Kasei, 1988 | BS |
Tboil | 399.8 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 397. | K | N/A | Cossar, Fournier, et al., 1962 | Uncertainty assigned by TRC = 2.5 K; TRC |
Tboil | 398. | K | N/A | Mann and Purdie, 1935 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 197.5 | K | N/A | Teets, 1934 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 197.5 | K | N/A | Ellis and Reid, 1932 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 197.45 | K | N/A | Finke, McCullough, et al., 1970 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 197.46 | K | N/A | Finke, Scott, et al., 1952, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 597.7 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 41.26 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 41.1 | kJ/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 41.1 | kJ/mol | V | Finke, Hossenlopp, et al., 1965 | vapor flow calorimetry; ALS |
ΔvapH° | 41.2 | kJ/mol | N/A | Hubbard, Katz, et al., 1954 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
34.88 | 399.8 | N/A | Majer and Svoboda, 1985 | |
40.6 | 315. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 300. to 426. K.; AC |
38.1 | 362. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 347. to 440. K. See also Finke, Scott, et al., 1952 and Osborn and Douslin, 1966.; AC |
37.1 ± 0.1 | 356. | C | Finke, Hossenlopp, et al., 1965, 2 | AC |
36.4 ± 0.1 | 376. | C | Finke, Hossenlopp, et al., 1965, 2 | AC |
34.9 ± 0.1 | 400. | C | Finke, Hossenlopp, et al., 1965, 2 | 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)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
356. to 400. | 57.97 | 0.2863 | 597.7 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
349.62 to 439.46 | 4.05801 | 1369.479 | -61.836 | Osborn and Douslin, 1966 |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
17.531 | 197.46 | Finke, Scott, et al., 1952 | DH |
17.53 | 197.5 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
88.78 | 197.46 | Finke, Scott, et al., 1952 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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
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
C5H11S- + =
By formula: C5H11S- + H+ = C5H12S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1475. ± 10. | kJ/mol | D-EA | Janousek, Reed, et al., 1980 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1449. ± 10. | kJ/mol | H-TS | Janousek, Reed, et al., 1980 | gas phase; B |
By formula: 2C5H12S + I2 = 2HI + C10H22S2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -124.9 | kJ/mol | Cm | Sunner, 1955, 2 | liquid phase; solvent: Ethanol/water(90/10); ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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: John E. Bartmess
De-protonation reactions
C5H11S- + =
By formula: C5H11S- + H+ = C5H12S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1475. ± 10. | kJ/mol | D-EA | Janousek, Reed, et al., 1980 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1449. ± 10. | kJ/mol | H-TS | Janousek, Reed, et al., 1980 | gas phase |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sunner, 1963
Sunner, S.,
Corrected heat of combustion and formation values for a number of organic sulphur compounds,
Acta Chem. Scand., 1963, 17, 728-730. [all data]
Hubbard, Katz, et al., 1954
Hubbard, W.N.; Katz, C.; Waddington, G.,
A rotating combustion bomb for precision calorimetry. Heats of combustion of some sulfur-containing compounds,
J. Phys. Chem., 1954, 58, 142. [all data]
Sunner, 1955
Sunner, S.,
Thermochemical investigation on organic sulfur compounds IV. On thermochemical sulfur bond energy terms,
Acta Chem. Scand., 1955, 9, 837-846. [all data]
Berthelot, 1901
Berthelot, M.,
Chimie Organique. - Nouvelles recherches sur l'isomerie des ethers sulfocyaniques,
Compt. Rend., 1901, 132, 57-58. [all data]
Finke, Scott, et al., 1952
Finke, H.L.; Scott, D.W.; Gross, M.E.; Waddington, G.; Huffman, H.M.,
The entropy and vapor pressure of 1-pentanethiol,
J. Am. Chem. Soc., 1952, 74, 2804-2806. [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]
American Tokyo Kasei, 1988
American Tokyo Kasei,
TCI American Organic Chemical 88/89 Catalog, American Tokyo Kasei, Portland, OR, 1988, 1610. [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]
Cossar, Fournier, et al., 1962
Cossar, B.C.; Fournier, J.O.; Fields, D.L.; Reynolds, D.D.,
Prepartion of Thiols,
J. Org. Chem., 1962, 27, 93. [all data]
Mann and Purdie, 1935
Mann, F.G.; Purdie, D.,
The Constitution of Complex Metallic Salts III. The Parachors of Palladium and Mercury in Simple and Complex Compounds,
J. Chem. Soc., 1935, 1935, 1549. [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]
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]
Finke, Scott, et al., 1952, 2
Finke, H.L.; Scott, D.W.; Gross, M.E.; Waddington, G.; Huffman, H.M.,
The entropy and vapor pressure of 1-pentanethiol,
J. Am. Chem. Soc., 1952, 74, 2804. [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]
Finke, Hossenlopp, et al., 1965
Finke, H.L.; Hossenlopp, I.A.; Berg, W.T.,
1-pentanethiol: Heat of vaporization and heat capacity of the vapor,
J. Phys. Chem., 1965, 69, 3030. [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]
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]
Finke, Hossenlopp, et al., 1965, 2
Finke, Herman L.; Hossenlopp, Isham A.; Berg, William T.,
1-Pentanethiol: Heat of Vaporization and Heat Capacity of the Vapor 1,
J. Phys. Chem., 1965, 69, 9, 3030-3031, https://doi.org/10.1021/j100893a035
. [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]
Sunner, 1955, 2
Sunner, S.,
Strain in 6,8-thioctic acid,
Nature (London), 1955, 176, 217. [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, IR Spectrum, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature 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 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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