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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -62.76 ± 0.21 | kcal/mol | Ccb | Harrop, Head, et al., 1970 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 33.360 | 358.15 | Hales J.L., 1967 | GT |
| 35.091 | 383.15 | ||
| 36.869 | 408.15 | ||
| 38.540 | 433.15 | ||
| 39.859 | 453.15 | ||
| 41.130 | 473.15 |
Condensed phase thermochemistry data
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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 | -71.58 ± 0.21 | kcal/mol | Ccb | Harrop, Head, et al., 1970 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -740.3 ± 0.2 | kcal/mol | Ccb | Harrop, Head, et al., 1970 | Corresponding ΔfHºliquid = -71.575 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 64.17 | cal/mol*K | N/A | Andon, Counsell, et al., 1968 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 43.02 | 298.15 | Harrop, Head, et al., 1970 | DH |
| 43.00 | 298.15 | Andon, Counsell, et al., 1968 | T = 10 to 320 K.; DH |
Reaction thermochemistry data
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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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Harrop, Head, et al., 1970
Harrop, D.; Head, A.J.; Lewis, G.B.,
Thermodynamic properties of organic oxygen compounds. 22. Enthalpies of combustion of some aliphatic ketones,
J. Chem. Thermodyn., 1970, 2, 203-210. [all data]
Hales J.L., 1967
Hales J.L.,
Thermodynamic properties of organic oxygen compounds. Part 18. Vapor heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether,
Trans. Faraday Soc., 1967, 63, 1876-1879. [all data]
Andon, Counsell, et al., 1968
Andon, R.J.L.; Counsell, J.F.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds. Part XX. The low-temperature heat capacity and entropy of C4 and C5 ketones,
J. Chem. Soc. A, 1968, 1894-1897. [all data]
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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid 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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