2-Butanol
- Formula: C4H10O
- Molecular weight: 74.1216
- IUPAC Standard InChI: InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3
- IUPAC Standard InChIKey: BTANRVKWQNVYAZ-UHFFFAOYSA-N
- CAS Registry Number: 78-92-2
- 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. - Species with the same structure:
- Stereoisomers:
- Other names: sec-Butyl Alcohol; sec-Butanol; CCS 301; Ethyl methyl carbinol; Methyl ethyl carbinol; 1-Methyl-1-propanol; 1-Methylpropyl alcohol; 2-Hydroxybutane; sec-C4H9OH; Butane, 2-hydroxy-; Butanol-2; Butan-2-ol; 2-Butyl alcohol; s-Butyl alcohol; Butylene hydrate; DL-sec-Butanol; DL-2-Butanol; Alcool butylique secondaire; Butanol secondaire; s-Butanol; 1-Methyl propanol; n-Butan-2-ol; NSC 25499
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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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 9.88 ± 0.03 | eV | N/A | N/A | L |
| Quantity | Value | Units | Method | Reference | Comment |
| Proton affinity (review) | 815. | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 784.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.88 ± 0.03 | PIPECO | Shao, Baer, et al., 1988 | LL |
| 9.88 ± 0.07 | EI | Bowen and Maccoll, 1984 | LBLHLM |
| 9.88 | EI | Holmes, Burgers, et al., 1982 | LBLHLM |
| 9.88 | EI | Holmes, Fingas, et al., 1981 | LLK |
| 10.23 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
| 10.35 ± 0.03 | PE | Peel and Willett, 1975 | Vertical value; LLK |
Appearance energy determinations
De-protonation reactions
C4H9O- + =
By formula: C4H9O- + H+ = C4H10O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1565. ± 8.4 | kJ/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrH° | 1566. ± 8.8 | kJ/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 1565. ± 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° | 1538. ± 8.8 | kJ/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrG° | 1538. ± 8.4 | kJ/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 1538. ± 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 ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Shao, Baer, et al., 1988
Shao, J.D.; Baer, T.; Lewis, D.K.,
Dissociation dynamics of energy-selected ion-dipole complexes. 2. Butyl alcohol ions,
J. Phys. Chem., 1988, 92, 5123. [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, Burgers, et al., 1982
Holmes, J.L.; Burgers, P.C.; Mollah, Y.A.,
Alkane elimination from ionized alkanols,
Org. Mass Spectrom., 1982, 17, 127. [all data]
Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P.,
Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations,
Can. J. Chem., 1981, 59, 80. [all data]
Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G.,
Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules,
J. Am. Chem. Soc., 1977, 99, 3980. [all data]
Peel and Willett, 1975
Peel, J.B.; Willett, G.D.,
Photoelectron spectroscopic studies of the higher alcohols,
Aust. J. Chem., 1975, 28, 2357. [all data]
Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L.,
Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks,
Org. Mass Spectrom., 1982, 17, 123. [all data]
Holmes, Rye, et al., 1979
Holmes, J.L.; Rye, R.T.B.; Terlouw, J.K.,
On the loss of ethylene from [C3H7O]+ ions of structure CH3CH2CHOH,
Org. Mass Spectrom., 1979, 14, 606. [all data]
Harrison, Ivko, et al., 1966
Harrison, A.G.; Ivko, A.; Van Raalte, D.,
Energetics of formation of some oxygenated ions and the proton affinities of carbonyl compounds,
Can. J. Chem., 1966, 44, 1625. [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]
Lossing, 1977
Lossing, F.P.,
Heats of formation of some isomeric [CnH2n+1]+ ions. Substitutional effects on ion stability,
J. Am. Chem. Soc., 1977, 99, 7526. [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]
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]
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 IE (evaluated) Recommended ionization 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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