1-Propanethiol, 2-methyl-
- Formula: C4H10S
- Molecular weight: 90.187
- IUPAC Standard InChIKey: BDFAOUQQXJIZDG-UHFFFAOYSA-N
- CAS Registry Number: 513-44-0
- 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: Isobutyl mercaptan; 1-Isobutanethiol; 2-Methyl-1-propanethiol; iso-C4H9SH; Isobutanethiol; 2-Methyl-1-propylthiol; 2-Methyl propanethiol; 2-methylpropane-1-thiol
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -23.06 ± 0.21 | kcal/mol | Ccr | Hubbard, Good, et al., 1958 |
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 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 | -31.55 ± 0.21 | kcal/mol | Ccr | Hubbard, Good, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -31.36 ± 0.21 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -830.19 ± 0.17 | kcal/mol | Ccr | Hubbard, Good, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -830.02 ± 0.17 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 63.659 | cal/mol*K | N/A | Scott, McCullough, et al., 1958 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.080 | 298.15 | Scott, McCullough, et al., 1958 | T = 10 to 350 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, 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 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 | 361. ± 1. | K | AVG | N/A | Average of 11 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 128.29 | K | N/A | Morris, Lanum, et al., 1960 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 128.31 | K | N/A | Scott, McCullough, et al., 1958, 2 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 559.5 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.296 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 8.27 | kcal/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 8.30 ± 0.02 | kcal/mol | E | Hubbard, Good, et al., 1958 | ALS |
ΔvapH° | 8.48 | kcal/mol | N/A | Hubbard, Good, et al., 1958 | DRB |
ΔvapH° | 8.30 | kcal/mol | V | Scott, McCullough, et al., 1958 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.412 | 361.6 | N/A | Majer and Svoboda, 1985 | |
8.03 | 329. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 314. to 399. K. See also Scott, McCullough, et al., 1958 and Osborn and Douslin, 1966.; AC |
7.96 ± 0.02 | 321. | C | Scott, McCullough, et al., 1958 | AC |
7.72 ± 0.02 | 340. | C | Scott, McCullough, et al., 1958 | AC |
7.41 ± 0.02 | 361. | C | Scott, McCullough, et al., 1958 | 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)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
321. to 362. | 11.91 | 0.2813 | 559.5 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
315.4 to 398.36 | 4.00665 | 1237.282 | -52.837 | Osborn and Douslin, 1966 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.1908 | 128.31 | Scott, McCullough, et al., 1958 | DH |
1.19 | 128.3 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
92.81 | 128.31 | Scott, McCullough, et al., 1958 | DH |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 191.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 184.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.12 | PE | Ogata, Onizuka, et al., 1973 | LLK |
De-protonation reactions
C4H9S- + =
By formula: C4H9S- + H+ = C4H10S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 353.1 ± 2.2 | kcal/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 346.8 ± 2.0 | kcal/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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 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 | Japan AIST/NIMC Database- Spectrum MS-NW-3789 |
NIST MS number | 231053 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hubbard, Good, et al., 1958
Hubbard, W.N.; Good, W.D.; Waddington, G.,
The heats of combustion, formation and isomerization of the seven isomeric C4H10S alkane thiols and sulfides,
J. Phys. Chem., 1958, 62, 614-617. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Scott, McCullough, et al., 1958
Scott, D.W.; McCullough, J.P.; Messerly, J.F.; Pennington, R.E.; Hossenlopp, I.A.; Finke, H.L.; Waddington, G.,
2-Methyl-1-propanethiol: Chemical thermodynamic properties and rotational isomerism,
J. Am. Chem. Soc., 1958, 80, 55-59. [all data]
Morris, Lanum, et al., 1960
Morris, J.C.; Lanum, W.J.; Helm, R.V.; Haines, W.E.; Cook, G.L.; Ball, J.S.,
Purification and Properties of Ten Organic Sulfur Compounds,
J. Chem. Eng. Data, 1960, 5, 112-6. [all data]
Scott, McCullough, et al., 1958, 2
Scott, D.W.; McCullough, J.P.; Messerly, J.F.; Pennington, R.E.; Hossenlopp, I.A.; Finke, H.L.; Waddington, G.,
2-Methyl-1-propanethiol: Chemical Thermodynamic properties and Rotational isomerism.,
J. Am. Chem. Soc., 1958, 80, 55-9. [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]
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]
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]
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]
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]
Taft, 1987
Taft, R.W.,
The Nature and Analysis of Substitutent Electronic Effects,
Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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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