3,3-Dimethylbutane-2-ol
- Formula: C6H14O
- Molecular weight: 102.1748
- IUPAC Standard InChI: InChI=1S/C6H14O/c1-5(7)6(2,3)4/h5,7H,1-4H3
- IUPAC Standard InChIKey: DFOXKPDFWGNLJU-UHFFFAOYSA-N
- CAS Registry Number: 464-07-3
- 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: Pinacolyl alcohol; 2-Butanol, 3,3-dimethyl-; tert-Butyl Methyl carbinol; 2,2-Dimethyl-3-butanol; 3,3-Dimethyl-2-butanol; (CH3)3CCH(CH3)OH; Pinacolyl alcohol-tert-butyl methylcarbinol; 3,3-dimethylbutan-2-ol
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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
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C2H5O+ | 10.14 | (CH3)3C | EI | Holmes, Lossing, et al., 1988 | LL |
| C2H5O+ | 10.12 ± 0.05 | tert-C4H9 | EI | Holmes and Lossing, 1984 | LBLHLM |
De-protonation reactions
C6H13O- + =
By formula: C6H13O- + H+ = C6H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 371.9 ± 2.0 | kcal/mol | D-EA | Mihalick, Gatev, et al., 1996 | gas phase; Derived BDE: 103.3±2.8 kcal/mol; B |
| ΔrH° | 371.4 ± 2.0 | kcal/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrH° | 371.1 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 365.1 ± 2.0 | kcal/mol | IMRE | Clifford, Wenthold, et al., 1998 | gas phase; B |
| ΔrG° | 365.3 ± 2.1 | kcal/mol | H-TS | Mihalick, Gatev, et al., 1996 | gas phase; Derived BDE: 103.3±2.8 kcal/mol; B |
| ΔrG° | 364.8 ± 2.1 | kcal/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrG° | 364.5 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | 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.
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]
Holmes and Lossing, 1984
Holmes, J.L.; Lossing, F.P.,
Heats of formation of organic radicals from appearance energies,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 113. [all data]
Mihalick, Gatev, et al., 1996
Mihalick, J.E.; Gatev, G.G.; Brauman, J.I.,
Electron Photodetachment Spectroscopy of Solvated Anions: RO.HF- or ROH.F-?,
J. Am. Chem. Soc., 1996, 118, 49, 12424, https://doi.org/10.1021/ja954202k
. [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]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Clifford, Wenthold, et al., 1998
Clifford, E.P.; Wenthold, P.G.; Gareyev, R.; Lineberger, W.C.; DePuy, C.H.; Bierbaum, V.M.; Ellison, G.B.,
Photoelectron spectroscopy, gas phase acidity, and thermochemistry of tert-butyl hydroperoxide: Mechanisms for the rearrangement of peroxyl radicals,
J. Chem. Phys., 1998, 109, 23, 10293-10310, https://doi.org/10.1063/1.477725
. [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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