2-Butanol, 3-methyl-
- Formula: C5H12O
- Molecular weight: 88.1482
- IUPAC Standard InChIKey: MXLMTQWGSQIYOW-UHFFFAOYSA-N
- CAS Registry Number: 598-75-4
- 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. - Stereoisomers:
- Other names: sec-Isoamyl alcohol; Methylisopropylcarbinol; 3-Methyl-2-butanol; (CH3)2CHCH(OH)CH3; (.+/-.)-3-Methyl-2-butanol; Butan-2-ol, 3-methyl-; 3-Methyl-butan-2-ol; 1,2-Dimethyl-1-propanol; 1,2-Dimethylpropanol; 2-Methyl-3-butanol; NSC 71162
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Condensed phase thermochemistry data
Go To: Top, 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 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 | -369.9 ± 1.4 | kJ/mol | Eqk | Connett, 1970 | ALS |
ΔfH°liquid | -366.6 ± 0.71 | kJ/mol | Ccb | Chao and Rossini, 1965 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3315.1 ± 0.63 | kJ/mol | Ccb | Chao and Rossini, 1965 | Corresponding ΔfHºliquid = -367.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
245.9 | 298.15 | Atrashenok, Nesterov, et al., 1991 | T = 218 to 373 K. Cp(liq) = 4.81853 - 3.12708(T/100) + 0.182356(T/100)2 + 0.484126(T/100)3 - 0.0905712(T/100)4 kJ/kg*K.; 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 385. ± 3. | K | AVG | N/A | Average of 23 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 131.5 | K | N/A | Zubkov, Peshenko, et al., 1990 | Glass phase; Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 556.1 ± 0.5 | K | N/A | Gude and Teja, 1995 | |
Tc | 556.1 | K | N/A | Quadri, Khilar, et al., 1991 | Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 38.7 ± 0.2 | bar | N/A | Gude and Teja, 1995 | |
Pc | 38.70 | bar | N/A | Quadri, Khilar, et al., 1991 | Uncertainty assigned by TRC = 0.40 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 53.03 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 51.6 ± 0.3 | kJ/mol | GS | Kulikov, Verevkin, et al., 2001 | Based on data from 280. to 301. K.; AC |
ΔvapH° | 53.5 ± 0.4 | kJ/mol | V | Connett, 1970 | ALS |
ΔvapH° | 51.7 | kJ/mol | C | McCurdy and Laidler, 1963 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
49.0 | 295. | A | Stephenson and Malanowski, 1987 | Based on data from 280. to 375. K.; AC |
46.4 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 293. to 385. K.; AC |
52.7 | 313. | N/A | Wilhoit and Zwolinski, 1973 | Based on data from 298. to 384. K.; AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change 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:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
View reactions leading to C5H12O+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.75 ± 0.05 | EI | George and Holmes, 1990 | LL |
10.01 ± 0.07 | EI | Bowen and Maccoll, 1984 | LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4O+ | 10.1 ± 0.1 | C3H8 | EI | George and Holmes, 1990 | LL |
C2H5O+ | 10.1 ± 0.05 | C3H7 | EI | George and Holmes, 1990 | LL |
C2H5O+ | 10.09 | 2-C3H7 | EI | Holmes, Lossing, et al., 1988 | LL |
C4H8O+ | 10.0 ± 0.1 | CH4 | EI | George and Holmes, 1990 | LL |
C4H9O+ | 9.90 ± 0.05 | CH3 | EI | George and Holmes, 1990 | LL |
De-protonation reactions
C5H11O- + =
By formula: C5H11O- + H+ = C5H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1559. ± 8.4 | kJ/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
ΔrH° | 1561. ± 12. | kJ/mol | G+TS | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1532. ± 8.8 | kJ/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
ΔrG° | 1533. ± 11. | kJ/mol | CIDC | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
Go To: Top, 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
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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-1316 |
NIST MS number | 233629 |
References
Go To: Top, 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.
Connett, 1970
Connett, J.E.,
Chemical equilibria. Part III. Dehydrogenation of pentan-1-ol, pentan-2-ol, and 3-methylbutan-2-ol,
J. Chem. Soc. A, 1970, 1284-1286. [all data]
Chao and Rossini, 1965
Chao, J.; Rossini, F.D.,
Heats of combustion, formation, and isomerization of nineteen alkanols,
J. Chem. Eng. Data, 1965, 10, 374-379. [all data]
Atrashenok, Nesterov, et al., 1991
Atrashenok, T.R.; Nesterov, N.A.; Zhuk, I.P.; Peshchenko, A.D.,
Measured specific heats of hexan-1-ol and 3-methyl-2-butanol over wide temperature ranges,
Inzh.-Fiz. Zh., 1991, 61(2), 301-304. [all data]
Zubkov, Peshenko, et al., 1990
Zubkov, V.I.; Peshenko, A.D.; Markovnik, V.S.,
Thermodynamic properties of 3-methyl-2-butanol and 3,3-dimethyl-2-butanol
in Vses. Konf. Term. Org. Soedin. 6th, Minsk, p 46, 1990. [all data]
Gude and Teja, 1995
Gude, M.; Teja, A.S.,
Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols,
J. Chem. Eng. Data, 1995, 40, 1025-1036. [all data]
Quadri, Khilar, et al., 1991
Quadri, S.K.; Khilar, K.C.; Kudchadker, A.P.; Patni, M.J.,
Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable alkanols,
J. Chem. Thermodyn., 1991, 23, 67-76. [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]
Kulikov, Verevkin, et al., 2001
Kulikov, Dmitry; Verevkin, Sergey P.; Heintz, Andreas,
Determination of Vapor Pressures and Vaporization Enthalpies of the Aliphatic Branched C 5 and C 6 Alcohols,
J. Chem. Eng. Data, 2001, 46, 6, 1593-1600, https://doi.org/10.1021/je010187p
. [all data]
McCurdy and Laidler, 1963
McCurdy, K.G.; Laidler, K.J.,
HEATS OF VAPORIZATION OF A SERIES OF ALIPHATIC ALCOHOLS,
Can. J. Chem., 1963, 41, 8, 1867-1871, https://doi.org/10.1139/v63-274
. [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]
Wilhoit and Zwolinski, 1973
Wilhoit, R.C.; Zwolinski, B.J.,
Physical and thermodynamic properties of aliphatic alcohols,
J. Phys. Chem. Ref. Data Suppl., 1973, 1, 2, 1. [all data]
George and Holmes, 1990
George, M.; Holmes, J.L.,
Intermediate ion structures in the fragmentation of metastable 3-methylbutan-2-ol radical cations,
Org. Mass Spectrom., 1990, 25, 605. [all data]
Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A.,
Low energy, low temperature mass spectra,
Org. Mass Spectrom., 1984, 19, 379. [all data]
Holmes, Lossing, et al., 1988
Holmes, J.L.; Lossing, F.P.; Maccoll, A.,
Heats of formation of alkyl radicals from appearance energies,
J. Am. Chem. Soc., 1988, 110, 7339. [all data]
Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G.,
The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols,
Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W
. [all data]
Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T.,
The gas phase acidity of aliphatic alcohols,
J. Am. Chem. Soc., 1983, 105, 2203. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid 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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