2-Butanol, 3-methyl-
- Formula: C5H12O
- Molecular weight: 88.1482
- IUPAC Standard InChI: InChI=1S/C5H12O/c1-4(2)5(3)6/h4-6H,1-3H3
- 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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Gas phase thermochemistry data
Go To: Top, Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -316.4 ± 1.8 | kJ/mol | Eqk | Connett, 1970 | ALS |
| ΔfH°gas | -313.1 | kJ/mol | N/A | Chao and Rossini, 1965 | Value computed using ΔfHliquid° value of -366.6±0.7 kj/mol from Chao and Rossini, 1965 and ΔvapH° value of 53.5 kj/mol from Connett, 1970.; DRB |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 388.6 ± 3.8 | J/mol*K | N/A | Connett, 1970 | This value was obtained from equilibrium study.; GT |
Condensed phase thermochemistry data
Go To: Top, Gas phase 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:
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 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase 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.
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]
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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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