Methyl vinyl ketone
- Formula: C4H6O
- Molecular weight: 70.0898
- IUPAC Standard InChIKey: FUSUHKVFWTUUBE-UHFFFAOYSA-N
- CAS Registry Number: 78-94-4
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: 3-Buten-2-one; Vinyl methyl ketone; 1-Buten-3-one; 2-Butenone; 3-Butene-2-one; CH2=CHCOCH3; Acetone, methylene-; Butenone; Ketone, methyl vinyl; Methyl ethenyl ketone; Methyl-vinyl-cetone; Methylvinylketon; Acetyl ethylene; Methylene acetone; γ-Oxo-α-butylene; UN 1251; 3-Oxobutene; 3-Butenen-2-one; But-3-en-2-one; 3-Oxo-1-butene; NSC 4853
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry 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 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 | -27.4 ± 2.6 | kcal/mol | Eqk | Guthrie, 1978 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 76.563 | cal/mol*K | N/A | Kharitonov Yu.Ya., 1987 | This 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
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 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 |
---|---|---|---|---|---|
Tboil | 354.6 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 354. | K | N/A | Murata, Arai, et al., 1957 | Uncertainty assigned by TRC = 4. K; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
309.8 | 0.191 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.86 | 294. | A | Stephenson and Malanowski, 1987 | Based on data from 279. to 355. K.; AC |
8.03 | 315. | A | Stephenson and Malanowski, 1987 | Based on data from 300. to 355. K.; AC |
Reaction thermochemistry data
Go To: Top, Gas 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 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- + =
By formula: C4H5O- + H+ = C4H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 363.3 ± 2.1 | kcal/mol | G+TS | Bartmess and Kiplinger, 1986 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 356.5 ± 2.0 | kcal/mol | IMRE | Bartmess and Kiplinger, 1986 | gas phase; value altered from reference due to change in acidity scale; B |
(CAS Reg. No. 71695-01-7 • 4294967295) + = CAS Reg. No. 71695-01-7
By formula: (CAS Reg. No. 71695-01-7 • 4294967295C4H6O) + C4H6O = CAS Reg. No. 71695-01-7
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 23.5 ± 4.6 | kcal/mol | N/A | Graul and Squires, 1990 | gas phase; B |
By formula: H2 + C4H6O = C4H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -131.6 | kcal/mol | Chyd | Veselova and Sul'man, 1980 | liquid phase; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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 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 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 199.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 191.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.66 | PE | Morizur, Mercier, et al., 1982 | LBLHLM |
9.64 | EI | Terlouw, Heerma, et al., 1980 | LLK |
9.66 | PE | Masclet and Mouvier, 1978 | LLK |
10.11 | PE | Kobayashi, 1978 | Vertical value; LLK |
9.61 | PE | Tam, Yee, et al., 1974 | Vertical value; LLK |
9.67 | PE | Hentrich, Gunkel, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O+ | 12.40 | C2H3 | EI | Majer, Patrick, et al., 1961 | RDSH |
C3H3O+ | 10.44 ± 0.05 | CH3 | EI | Holmes, Terlouw, et al., 1980 | LLK |
C3H3O+ | 10.85 | CH3 | EI | Majer, Patrick, et al., 1961 | RDSH |
De-protonation reactions
C4H5O- + =
By formula: C4H5O- + H+ = C4H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 363.3 ± 2.1 | kcal/mol | G+TS | Bartmess and Kiplinger, 1986 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 356.5 ± 2.0 | kcal/mol | IMRE | Bartmess and Kiplinger, 1986 | gas phase; value altered from reference due to change in acidity scale; B |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes
Data compiled by: Coblentz Society, Inc.
- Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- GAS (50 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1340, 10% IN CS2 FOR 1340-400 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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
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-IW-3441 |
NIST MS number | 230322 |
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.
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).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
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 α,β-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
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy S°gas Entropy of gas at standard conditions Tboil Boiling point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.