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3-Penten-2-one, 4-methyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
Deltafgas-42.61 ± 0.15kcal/molCcbSteele, Chirico, et al., 1997 
Deltafgas-44.10 ± 0.59kcal/molEqkGuthrie, 1978 

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid-52.82 ± 0.14kcal/molCcbSteele, Chirico, et al., 1997 
Deltafliquid-52.4 ± 0.2kcal/molCcbLebedeva, Gutner, et al., 1976 
Quantity Value Units Method Reference Comment
Deltacliquid-853.07 ± 0.11kcal/molCcbSteele, Chirico, et al., 1997Corresponding «DELTA»fliquid = -52.815 kcal/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-853.5 ± 0.2kcal/molCcbLebedeva, Gutner, et al., 1976Corresponding «DELTA»fliquid = -52.4 kcal/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-846.1kcal/molCcbGuinchant, 1918Corresponding «DELTA»fliquid = -59.8 kcal/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-848.2kcal/molCcbRoth-Greifswald, 1911Heat of combustion corrected for pressure; Corresponding «DELTA»fliquid = -57.7 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change 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:
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
Tboil403. ± 1.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus226.75KN/AAnonymous, 1968TRC
Tfus220.3KN/AStross, Monger, et al., 1947Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tc605.KN/ASteele, Chirico, et al., 1997, 2Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc39.48atmN/ASteele, Chirico, et al., 1997, 2Uncertainty assigned by TRC = 1.48 atm; derived from fit of obs. vapor pressure; TRC
Quantity Value Units Method Reference Comment
rhoc2.830mol/lN/ASteele, Chirico, et al., 1997, 2Uncertainty assigned by TRC = 0.10 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap10.21 ± 0.067kcal/molVSteele, Chirico, et al., 1997ALS
Deltavap10.2 ± 0.07kcal/molEBSteele, Chirico, et al., 1997, 3Based on data from 303. - 442. K.; AC
Deltavap10.7kcal/molCGCChickos, Hosseini, et al., 1995Based on data from 343. - 383. K.; AC
Deltavap10.3kcal/molN/AMesserly, Finke, et al., 1975Based on data from 292. - 471. K.; AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
9.89 ± 0.07320.EBSteele, Chirico, et al., 1997, 3Based on data from 303. - 442. K.; AC
9.35 ± 0.07360.EBSteele, Chirico, et al., 1997, 3Based on data from 303. - 442. K.; AC
8.72 ± 0.07400.EBSteele, Chirico, et al., 1997, 3Based on data from 303. - 442. K.; AC
8.0 ± 0.1440.EBSteele, Chirico, et al., 1997, 3Based on data from 303. - 442. K.; AC
9.03414.AStephenson and Malanowski, 1987Based on data from 399. - 471. K.; AC
9.92328.MMStephenson and Malanowski, 1987Based on data from 313. - 405. K. See also Stross, Monger, et al., 1947, 2 and Dykyj, 1972.; AC
8.41401.N/ALouguinine, 1898May 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)

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Temperature (K) A B C Reference Comment
287. - 403.14.187821434.631-60.088Fuge, Bowden, et al., 1952Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
2.89229.6Borgen, Borgen, et al., 1975AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Gas phase ion energetics 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 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 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)210.0kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity202.4kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.11PEMasclet and Mouvier, 1978LLK
9.08 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
8.89 ± 0.05EIOmura, Higasi, et al., 1956RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H7O+9.48CH3EIAlai, Attardo, et al., 1985LBLHLM

IR Spectrum

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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 by: Coblentz Society, Inc.

Gas Phase Spectrum

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IR spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner COBLENTZ SOCIETY
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin PERKIN-ELMER CORP. (M. ZELLER)
Source reference COBLENTZ NO. 10525
Date 1977/07/18
Name(s) MESITYL OXIDE
State VAPOR (15 MICROLITER AT 150 C)
Instrument PERKIN-ELMER 180
Instrument parameters
ABSORPTIONS AT 1058 AND 1053 CM-1 ARE AFFECTED BY AN UNKNOWN.
Path length 5 CM KBr CELL, CELL VOLUME: 80 CM3
Resolution 2-3 CM-1
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS)
Boiling point 131 C

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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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Mass spectrum
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Additional Data

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Timmons, 1966
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 19939
Instrument Unicam SP 700
Boiling point 130-131

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Lebedeva, Gutner, et al., 1976
Lebedeva, N.D.; Gutner, N.M.; Kiseleva, N.N., Correlation of the departures from additivity in the enthalpies of formation of ethylene and benzene derivatives with the «sigma»p constants, J. Org. Chem. USSR (Engl. Transl.), 1976, 12, 1594-1597. [all data]

Guinchant, 1918
Guinchant, M.J., Etude sur la fonction acide dans les derives metheniques et methiniques, Ann. Chem., 1918, 10, 30-84. [all data]

Roth-Greifswald, 1911
Roth-Greifswald, W.A., XVIII. Hauptversammlung der Deutschen Bunsen-Gesellschaft fur angewandte physikalische Chemie, Z. Electrochem., 1911, 17, 789-840. [all data]

Anonymous, 1968
Anonymous, X., Chemicals and Plastics Physical Properties, 1968, Union Carbide Corp., product bulletin, 1968. [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]

Timmons, 1966
Timmons, C.J., UV atlas of organic compounds, 1966, 1, B 3/2. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References