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 ion energetics data
Go To: Top, 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° | 372.7 ± 2.0 | kcal/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrH° | 373.0 ± 2.8 | kcal/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° | 366.1 ± 2.1 | kcal/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrG° | 366.4 ± 2.7 | kcal/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 ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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 ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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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