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Methyl vinyl ketone

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Gas 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-115. ± 11.kJ/molEqkGuthrie, 1978ALS
Quantity Value Units Method Reference Comment
gas320.34J/mol*KN/AKharitonov Yu.Ya., 1987This value was calculated by statistical mechanical method. Statistically calculated thermodynamic functions of [ Anjaneyulu Y., 1988] (S(300 K)=301.65 and Cp(300 K)=79.23 J/mol*K) seem to be erroneous. Values of S(298.15 K)=316.5 and Cp(298.15 K)=92.2 J/mol*K were calculated from data for related aldehydes and ketones by difference method [ Dorofeeva O.V., 1997].; GT

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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil354.6KN/AWeast and Grasselli, 1989BS
Tboil354.KN/AMurata, Arai, et al., 1957Uncertainty assigned by TRC = 4. K; TRC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
309.80.193Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
32.9294.AStephenson and Malanowski, 1987Based on data from 279. - 355. K.; AC
33.6315.AStephenson and Malanowski, 1987Based on data from 300. - 355. K.; AC

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:


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

C4H5O- + Hydrogen cation = Methyl vinyl ketone

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Deltar1520. ± 8.8kJ/molG+TSBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1492. ± 8.4kJ/molIMREBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale; B

(CAS Reg. No. 71695-01-7 bullet 4294967295Methyl vinyl ketone) + Methyl vinyl ketone = CAS Reg. No. 71695-01-7

By formula: (CAS Reg. No. 71695-01-7 bullet 4294967295C4H6O) + C4H6O = CAS Reg. No. 71695-01-7

Quantity Value Units Method Reference Comment
Deltar98. ± 19.kJ/molN/AGraul and Squires, 1990gas phase; B

Hydrogen + Methyl vinyl ketone = 2-Butanone

By formula: H2 + C4H6O = C4H8O

Quantity Value Units Method Reference Comment
Deltar-550.6kJ/molChydVeselova and Sul'man, 1980liquid phase; ALS

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:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C4H6O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.65 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)834.7kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity802.8kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.66PEMorizur, Mercier, et al., 1982LBLHLM
9.64EITerlouw, Heerma, et al., 1980LLK
9.66PEMasclet and Mouvier, 1978LLK
10.11PEKobayashi, 1978Vertical value; LLK
9.61PETam, Yee, et al., 1974Vertical value; LLK
9.67PEHentrich, Gunkel, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+12.40C2H3EIMajer, Patrick, et al., 1961RDSH
C3H3O+10.44 ± 0.05CH3EIHolmes, Terlouw, et al., 1980LLK
C3H3O+10.85CH3EIMajer, Patrick, et al., 1961RDSH

De-protonation reactions

C4H5O- + Hydrogen cation = Methyl vinyl ketone

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Deltar1520. ± 8.8kJ/molG+TSBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1492. ± 8.4kJ/molIMREBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.


Mass spectrum (electron ionization)

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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: 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-IW-3441
NIST MS number 230322

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, Phase change data, Reaction thermochemistry 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 Bol'shakov, et al., 1969
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. 20219
Instrument unknown
Boiling point 81.4

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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.

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]

Kharitonov Yu.Ya., 1987
Kharitonov Yu.Ya., Thermodynamic properties of methylvinylketone calculated by statistical mechanics. Deposited at ONIITEkhim, Cherkassy, Ukraine, 16.04.87, No. 417-xn 87 (From Ref. Zh. Khim. 1987, 15 B3025DP), 1987. [all data]

Anjaneyulu Y., 1988
Anjaneyulu Y., Thermodynamic functions of some acryl derivatives, J. Indian Chem. Soc., 1988, 65, 400-403. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Murata, Arai, et al., 1957
Murata, N.; Arai, H.; Tanaka, M., Synthesis of Methyl Vinyl Ketone, Kogyo Kagaku Zasshi, 1957, 60, 1206-7. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P., 'Kinetic' vs. thermodynamic acidities of enones in the gas phase, J. Org. Chem., 1986, 51, 2173. [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Veselova and Sul'man, 1980
Veselova, M.E.; Sul'man, E.M., Effect of the chemical structure of «alpha»,«beta»-unsaturated esters and ketones on the selectivity of their hydrogenation, Svoistva Veshchestv i Stroenie Molekul, Kalinin, 1980, 140-143. [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]

Morizur, Mercier, et al., 1982
Morizur, J.-P.; Mercier, J.; Sarraf, M., 2-Substituted-2,3-dihydro-4H-pyrans: Competition between 'Retro Diels-Alder' fragmentation and substituent loss, Org. Mass Spectrom., 1982, 17, 327. [all data]

Terlouw, Heerma, et al., 1980
Terlouw, J.K.; Heerma, W.; Holmes, J.L.; Burgers, P.C., Structure and formation of gaseous [C4H6O]+ ions. 1-The enolic ions [CH2=C(OH)-CH=CH2]+ and [CH2=CH-CH=CH(OH)]+ and their relationship with their keto counterparts, Org. Mass Spectrom., 1980, 15, 582. [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]

Kobayashi, 1978
Kobayashi, T., A new rule for photoelectron angular distributions of molecules, Phys. Lett. A, 1978, 69, 31. [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]

Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M., Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen, J. Mol. Struct., 1974, 21, 231. [all data]

Majer, Patrick, et al., 1961
Majer, J.R.; Patrick, C.R.; Robb, J.C., Appearance potentials of the acetyl radical-ion, J. Chem. Soc. Faraday Trans., 1961, 57, 14. [all data]

Holmes, Terlouw, et al., 1980
Holmes, J.L.; Terlouw, J.K.; Burgers, P.C., [C3H3O]+ ions; Reacting and non-reacting configurations, Org. Mass Spectrom., 1980, 15, 140. [all data]

Bol'shakov, et al., 1969
Bol'shakov, G.F., et al., Ultraviolet spectra of heteroorganic compounds, 1969, 260. [all data]


Notes

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