2-Butanone, 3-methyl-
- Formula: C5H10O
- Molecular weight: 86.1323
- IUPAC Standard InChI: InChI=1S/C5H10O/c1-4(2)5(3)6/h4H,1-3H3
- IUPAC Standard InChIKey: SYBYTAAJFKOIEJ-UHFFFAOYSA-N
- CAS Registry Number: 563-80-4
- 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. - Other names: Isopropyl methyl ketone; Ketone, isopropyl methyl; Methyl butanone-2; Methyl isopropyl ketone; 3-Methyl-2-butanone; iso-C3H7COCH3; 2-Acetylpropane; 3-Methylbutan-2-one; MIPK; UN 2397; 2-Methylbutan-3-one; NSC 9379; methylbutanone; 3-Methyl-2-butanoate; 3-methylbutanone
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Reaction thermochemistry 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C5H9O- + =
By formula: C5H9O- + H+ = C5H10O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 369.3 ± 2.7 | kcal/mol | G+TS | Chyall, Brickhouse, et al., 1994 | gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 362.8 ± 2.5 | kcal/mol | IMRE | Chyall, Brickhouse, et al., 1994 | gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol; B |
C5H9O- + =
By formula: C5H9O- + H+ = C5H10O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 367.3 ± 2.2 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 360.5 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; B |
(CAS Reg. No. 60375-60-2 • 4294967295) +
= CAS Reg. No. 60375-60-2
By formula: (CAS Reg. No. 60375-60-2 • 4294967295C5H10O) + C5H10O = CAS Reg. No. 60375-60-2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 40.3 ± 2.1 | kcal/mol | N/A | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrH° | 40.2 ± 2.9 | kcal/mol | Ther | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
+
=
+ 2
By formula: C7H16O2 + H2O = C5H10O + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 4.86 ± 0.01 | kcal/mol | Cm | Wiberg and Squires, 1979 | liquid phase; Heat of hydrolysis; ALS |
=
+
By formula: C5H12O = H2 + C5H10O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 12.9 ± 0.38 | kcal/mol | Eqk | Connett, 1970 | gas phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Chyall, Brickhouse, et al., 1994
Chyall, L.J.; Brickhouse, M.D.; Schnute, M.E.; Squires, R.R.,
Kinetic versus thermodynamic control in the deprotonation of unsymmetrical ketones in the gas phase,
J. Am. Chem. Soc., 1994, 116, 19, 8681, https://doi.org/10.1021/ja00098a031
. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [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]
Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R.,
Thermodynamics of hydrolysis aliphatic ketals. An entropy component of steric effects,
J. Am. Chem. Soc., 1979, 101, 5512-5515. [all data]
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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
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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