2-Butanone, 3-methyl-
- Formula: C5H10O
- Molecular weight: 86.1323
- 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, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 | -262.57 ± 0.87 | kJ/mol | Ccb | Harrop, Head, et al., 1970 | ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
139.58 | 358.15 | Hales J.L., 1967 | GT |
146.82 | 383.15 | ||
154.26 | 408.15 | ||
161.25 | 433.15 | ||
166.77 | 453.15 | ||
172.09 | 473.15 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -299.47 ± 0.86 | kJ/mol | Ccb | Harrop, Head, et al., 1970 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3097.2 ± 0.8 | kJ/mol | Ccb | Harrop, Head, et al., 1970 | Corresponding ΔfHºliquid = -299.47 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 268.5 | J/mol*K | N/A | Andon, Counsell, et al., 1968 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
180.0 | 298.15 | Harrop, Head, et al., 1970 | DH |
179.9 | 298.15 | Andon, Counsell, et al., 1968 | T = 10 to 320 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 367. ± 2. | K | AVG | N/A | Average of 40 out of 41 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 178.75 | K | N/A | Mears, Fookson, et al., 1950 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 181.15 | K | N/A | Timmermans and Mattaar, 1921 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 180.01 | K | N/A | Andon, Counsell, et al., 1968, 2 | Uncertainty assigned by TRC = 0.06 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 553.1 | K | N/A | Quadri and Kudchadker, 1991 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tc | 553.4 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 553.4 | K | N/A | Kobe, Crawford, et al., 1955 | Uncertainty assigned by TRC = 0.83 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 38.00 | bar | N/A | Quadri and Kudchadker, 1991 | Uncertainty assigned by TRC = 0.20 bar; TRC |
Pc | 38.50 | bar | N/A | Kobe, Crawford, et al., 1955 | Uncertainty assigned by TRC = 0.483 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.23 | mol/l | N/A | Kobe, Crawford, et al., 1955 | Uncertainty assigned by TRC = 0.29 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 36.87 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 36.81 | kJ/mol | V | Uchytilova, Majer, et al., 1983 | ALS |
ΔvapH° | 36.8 | kJ/mol | C | Uchytilova, Majer, et al., 1983 | AC |
ΔvapH° | 36.9 | kJ/mol | N/A | Ambrose, Ellender, et al., 1975 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
32.35 | 367.4 | N/A | Majer and Svoboda, 1985 | |
35.5 | 326. | A | Stephenson and Malanowski, 1987 | Based on data from 311. to 369. K.; AC |
33.8 | 378. | A | Stephenson and Malanowski, 1987 | Based on data from 363. to 415. K.; AC |
32.6 | 420. | A | Stephenson and Malanowski, 1987 | Based on data from 405. to 500. K.; AC |
35.0 | 343. | A | Stephenson and Malanowski, 1987 | Based on data from 328. to 377. K. See also Ambrose, Ellender, et al., 1975.; AC |
35.0 ± 0.1 | 327. | C | Hales, Lees, et al., 1967 | AC |
33.8 ± 0.1 | 346. | C | Hales, Lees, et al., 1967 | AC |
32.3 ± 0.1 | 367. | C | Hales, Lees, et al., 1967 | AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 368. | 53.89 | 0.2911 | 553.4 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
253.3 to 362.1 | 5.62559 | 1806.925 | -40.618 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.343 | 180.01 | Andon, Counsell, et al., 1968 | DH |
9.34 | 180. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
51.90 | 180.01 | Andon, Counsell, et al., 1968 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C5H10O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.31 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 836.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 804.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.298 ± 0.005 | PE | Hernandez, Masclet, et al., 1977 | LLK |
9.30 ± 0.01 | PE | Mouvier and Hernandez, 1975 | LLK |
9.30 ± 0.04 | EI | Mouvier and Hernandez, 1975 | LLK |
9.36 | PE | Tam, Yee, et al., 1974 | LLK |
9.30 ± 0.01 | PE | Cocksey, Eland, et al., 1971 | LLK |
9.30 ± 0.02 | PI | Murad and Inghram, 1964 | RDSH |
9.32 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O+ | 10.68 | ? | EI | Mouvier and Hernandez, 1975 | LLK |
C2H3O+ | 10.4 | iso-C3H7 | PI | Murad and Inghram, 1964 | RDSH |
C4H7O+ | 9.9 | ? | EI | Mouvier and Hernandez, 1975 | LLK |
C4H7O+ | 9.94 | CH3 | PI | Murad and Inghram, 1964 | RDSH |
De-protonation reactions
C5H9O- + =
By formula: C5H9O- + H+ = C5H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1545. ± 11. | kJ/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° | 1518. ± 10. | kJ/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° | 1537. ± 9.2 | kJ/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° | 1508. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | D.HENNEBERG, MAX-PLANCK INSTITUTE, MULHEIM, WEST GERMANY |
NIST MS number | 61712 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]
Mears, Fookson, et al., 1950
Mears, T.W.; Fookson, A.; Pomerantz, P.; Rich, E.H.; Dussinger, C.S.; Howard, F.L.,
Syntheses and Properties of Two Olefins, Six Paraffins, and Their Intermediates,
J. Res. Natl. Bur. Stand. (U. S.), 1950, 44, 299. [all data]
Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F.,
Freezing points of orgainic substances VI. New experimental determinations.,
Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]
Andon, Counsell, et al., 1968, 2
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, 1968, 1894-7. [all data]
Quadri and Kudchadker, 1991
Quadri, S.K.; Kudchadker, A.P.,
Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable esters, ketones, and ethers,
J. Chem. Thermodyn., 1991, 23, 129-34. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Kobe, Crawford, et al., 1955
Kobe, K.A.; Crawford, H.R.; Stephenson, R.W.,
Critical Properties and Vapor Pressures of Some Ketones,
Ind. Eng. Chem., 1955, 47, 1767-72. [all data]
Uchytilova, Majer, et al., 1983
Uchytilova, V.; Majer, V.; Svoboda, V.; Hynek, V.,
Enthalpies of vaporization and cohesive enrgies for seven aliphatic ketones,
J. Chem. Thermodyn., 1983, 15, 853-858. [all data]
Ambrose, Ellender, et al., 1975
Ambrose, D.; Ellender, J.H.; Lees, E.B.; Sprake, C.H.S.; Townsend, R.,
Thermodynamic properties of organic oxygen compounds XXXVIII. Vapour pressures of some aliphatic ketones,
The Journal of Chemical Thermodynamics, 1975, 7, 5, 453-472, https://doi.org/10.1016/0021-9614(75)90275-X
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Hales, Lees, et al., 1967
Hales, J.L.; Lees, E.B.; Ruxton, D.J.,
Thermodynamic properties of organic oxygen compounds. Part 18.-Vapour 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. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
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]
Hernandez, Masclet, et al., 1977
Hernandez, R.; Masclet, P.; Mouvier, G.,
Spectroscopie de photoelectrons d'aldehydes et de cetones aliphatiques,
J. Electron Spectrosc. Relat. Phenom., 1977, 10, 333. [all data]
Mouvier and Hernandez, 1975
Mouvier, G.; Hernandez, R.,
Ionisation and appearance potentials of alkylketones,
Org. Mass Spectrom., 1975, 10, 958. [all data]
Tam, Yee, et al., 1974
Tam, W.-C.; Yee, D.; Brion, C.E.,
Photoelectron spectra of some aldehydes and ketones,
J. Electron Spectrosc. Relat. Phenom., 1974, 4, 77. [all data]
Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J.,
The effect of alkyl substitution on ionisation potential,
J. Chem. Soc., 1971, (B), 790. [all data]
Murad and Inghram, 1964
Murad, E.; Inghram, M.G.,
Photoionization of aliphatic ketones,
J. Chem. Phys., 1964, 40, 3263. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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