3-Penten-2-one, 4-methyl-
- Formula: C6H10O
- Molecular weight: 98.1430
- IUPAC Standard InChIKey: SHOJXDKTYKFBRD-UHFFFAOYSA-N
- CAS Registry Number: 141-79-7
- 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: Acetone, isopropylidene-; Isobutenyl methyl ketone; Isopropylideneacetone; Mesityl oxide; Methyl isobutenyl ketone; Methyl 2-methyl-1-propenyl ketone; 4-Methyl-3-penten-2-one; (CH3)2C=CHC(=O)CH3; Methyl 2,2-dimethylvinyl ketone; 4-Methyl-3-pentene-2-one; 2-Methylpent-2-en-4-one; 2-Methyl-2-penten-4-one; Mesityloxid; Mesityloxyde; MIBK; Ossido di mesitile; Oxyde de mesityle; 3-Isohexen-2-one; 4-Methyl-3-penten-2-on; 4-Methylpent-3-en-2-one; 4-Metil-3-penten-2-one; 2-Methyl-2-pentenone-4; UN 1229; 2-Methyl-4-oxo-2-pentene; 2,2-Dimethylvinyl methyl ketone; NSC 38717; 4-methyl-3-penten-2-one (mesityl oxide)
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Gas phase thermochemistry data
Go To: Top, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -42.61 ± 0.15 | kcal/mol | Ccb | Steele, Chirico, et al., 1997 | |
ΔfH°gas | -44.10 ± 0.59 | kcal/mol | Eqk | Guthrie, 1978 |
Phase change data
Go To: Top, Gas 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 402. ± 1. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 220.3 | K | N/A | Stross, Monger, et al., 1947 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 605. | K | N/A | Steele, Chirico, et al., 1997, 2 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 39.48 | atm | N/A | Steele, Chirico, et al., 1997, 2 | Uncertainty assigned by TRC = 1.48 atm; derived from fit of obs. vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.830 | mol/l | N/A | Steele, Chirico, et al., 1997, 2 | Uncertainty assigned by TRC = 0.10 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.21 ± 0.067 | kcal/mol | V | Steele, Chirico, et al., 1997 | ALS |
ΔvapH° | 10.2 ± 0.07 | kcal/mol | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 303. to 442. K.; AC |
ΔvapH° | 10.7 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
ΔvapH° | 10.3 | kcal/mol | N/A | Messerly, Finke, et al., 1975 | Based on data from 292. to 471. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.89 ± 0.07 | 320. | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 303. to 442. K.; AC |
9.35 ± 0.07 | 360. | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 303. to 442. K.; AC |
8.72 ± 0.07 | 400. | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 303. to 442. K.; AC |
8.0 ± 0.1 | 440. | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 303. to 442. K.; AC |
9.03 | 414. | A | Stephenson and Malanowski, 1987 | Based on data from 399. to 471. K.; AC |
9.92 | 328. | MM | Stephenson and Malanowski, 1987 | Based on data from 313. to 405. K. See also Stross, Monger, et al., 1947, 2 and Dykyj, 1972.; AC |
8.41 | 401. | N/A | Louguinine, 1898 | May be a mixture of 2-methyl-1-penten-4-one and 4-methyl-3-penten-2-one; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
287. to 403.1 | 4.18782 | 1434.631 | -60.088 | Fuge, Bowden, et al., 1952 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.89 | 229.6 | Borgen, Borgen, et al., 1975 | AC |
Gas phase ion energetics data
Go To: Top, Gas 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
View reactions leading to C6H10O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.10 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 210.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 202.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.11 | PE | Masclet and Mouvier, 1978 | LLK |
9.08 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.89 ± 0.05 | EI | Omura, Higasi, et al., 1956 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H7O+ | 9.48 | CH3 | EI | Alai, Attardo, et al., 1985 | LBLHLM |
Mass spectrum (electron ionization)
Go To: Top, Gas 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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 | Japan AIST/NIMC Database- Spectrum MS-NW- 29 |
NIST MS number | 229805 |
References
Go To: Top, Gas 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.
Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A.,
Thermodynamic properties and ideal-gas enthalpies of formation for 2-aminoisobutyric acid (2-methylalanine), acetic acid, (4-methyl-3-penten-2-one), 4-methylpent-1-ene, 2,2'-bis(phenylthio)propane, and glycidyl phenyl ether (1,2-epoxy-3-phenoxypropane),
J. Chem. Eng. Data, 1997, 42, 1052-1066. [all data]
Guthrie, 1978
Guthrie, J.P.,
Equilibrium constants for a series of simple aldol condensations, and linear free energy relations with other carbonyl addition reactions,
Can. J. Chem., 1978, 56, 962-973. [all data]
Stross, Monger, et al., 1947
Stross, F.H.; Monger, J.M.; Finch, H. deV.,
Isolation and Purification of the Two Isomers of Mesityl Oxide,
J. Am. Chem. Soc., 1947, 69, 1627-8. [all data]
Steele, Chirico, et al., 1997, 2
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A.,
Thermodynamic Properties and Ideal-Gas Enthalpies of FOrmation for 2-Aminoisobutyric Acid (2-Methylalanine), Acetic Acid, (Z)-5-Ethylidene-2- norbornene, Mesityl Oxide (4-Methyl-3-pentene-2-one), 4-M,
J. Chem. Eng. Data, 1997, 42, 1053-66. [all data]
Steele, Chirico, et al., 1997, 3
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A.,
Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 2-Aminoisobutyric Acid (2-Methylalanine), Acetic Acid, ( Z )-5-Ethylidene-2-norbornene, Mesityl Oxide (4-Methyl-3-penten-2-one), 4-Methylpent-1-ene, 2,2'-Bis(phenylthio)propane, and Glycidyl Phenyl Ether (1,2-Epoxy-3-phenoxypropane),
J. Chem. Eng. Data, 1997, 42, 6, 1053-1066, https://doi.org/10.1021/je970099y
. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [all data]
Messerly, Finke, et al., 1975
Messerly, J.F.; Finke, H.L.; Osborn, A.G.; Douslin, D.R.,
Low-temperature calorimetric and vapor-pressure studies on alkanediamines,
J. Chem. Thermodynam., 1975, 7, 1029-1046. [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]
Stross, Monger, et al., 1947, 2
Stross, F.H.; Monger, J.M.; Finch, H. de V.,
The Isolation and Purification of Two Isomers of Mesityl Oxide,
J. Am. Chem. Soc., 1947, 69, 7, 1627-1628, https://doi.org/10.1021/ja01199a016
. [all data]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
Louguinine, 1898
Louguinine, W.,
Ann. Chim. (Paris), 1898, 7, 334. [all data]
Fuge, Bowden, et al., 1952
Fuge, E.T.J.; Bowden, S.T.; Jones, W.J.,
Some Physical Properties of Diacetone Alcohol, Mesityl Oxide and Methyl Isobutyl Ketone,
J. Phys. Chem., 1952, 56, 8, 1013-1016, https://doi.org/10.1021/j150500a022
. [all data]
Borgen, Borgen, et al., 1975
Borgen, Gerd; Borgen, Gerd; Dale, Johannes; Gaupset, Gudmund; Schroll, G.; Altona, C.,
Syntheses and Conformations of Monomeric and Dimeric Cyclic Dimethylketals.,
Acta Chem. Scand., 1975, 29b, 265-272, https://doi.org/10.3891/acta.chem.scand.29b-0265
. [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]
Masclet and Mouvier, 1978
Masclet, P.; Mouvier, G.,
Etude par spectrometrie photoelectronique d'aldehydes et de cetones ethyleniques conjugues,
J. Electron Spectrosc. Relat. Phenom., 1978, 14, 77. [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]
Omura, Higasi, et al., 1956
Omura, I.; Higasi, K.; Baba, H.,
Ionization potentials of some organic molecules. II. Aliphatic compounds,
Bull. Chem. Soc. Japan, 1956, 29, 504. [all data]
Alai, Attardo, et al., 1985
Alai, M.; Attardo, G.G.; Rye, R.T.B.,
Formation threshold structures of some [C5H7O]+ ions: Use of general schemes for estimation of heats of formation of gas phase ions,
Can. J. Chem., 1985, 63, 833. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion 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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