2-Propenoic acid, 2-methyl-
- Formula: C4H6O2
- Molecular weight: 86.0892
- IUPAC Standard InChIKey: CERQOIWHTDAKMF-UHFFFAOYSA-N
- CAS Registry Number: 79-41-4
- 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: Methacrylic acid; α-Methylacrylic acid; Methylacrylic acid; 2-Methyl-2-propenoic acid; 2-Methylacrylic acid; CH2=C(CH3)COOH; 2-Methylpropenoic acid; Methacrylic acid glacial; α-Methacrylic acid; Acrylic acid, 2-methyl-; Propionic acid, 2-methylene-; Kyselina methakrylova; NSC 7393
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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
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -87.79 ± 0.57 | kcal/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | ALS |
ΔfH°gas | -88.96 | kcal/mol | N/A | Lebedeva, Gutner, et al., 1976 | Value computed using ΔfHliquid° value of -419.7±0.4 kj/mol from Lebedeva, Gutner, et al., 1976 and ΔvapH° value of 47.5 kj/mol from Van-chin-syan, Kochubei, et al., 1996.; DRB |
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
C4H5O2- + =
By formula: C4H5O2- + H+ = C4H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 344.1 ± 2.9 | kcal/mol | G+TS | Graul, Schnute, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 337.1 ± 2.8 | kcal/mol | CIDC | Graul, Schnute, et al., 1990 | gas phase; B |
By formula: H2 + C4H6O2 = C4H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28.2 ± 0.3 | kcal/mol | Chyd | Skinner and Snelson, 1959 | liquid phase; solvent: Acetic acid; 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
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 195.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 187.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.15 | PE | Holmes, Terlouw, et al., 1979 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H4O+ | 10.64 | H2O | EI | Burgers, Holmes, et al., 1982 | LBLHLM |
De-protonation reactions
C4H5O2- + =
By formula: C4H5O2- + H+ = C4H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 344.1 ± 2.9 | kcal/mol | G+TS | Graul, Schnute, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 337.1 ± 2.8 | kcal/mol | CIDC | Graul, Schnute, et al., 1990 | gas phase; B |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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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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 | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 291422 |
UV/Visible 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.
Spectrum
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Additional Data
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Source | Fihtengolts, 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. 20127 |
Instrument | SF-4 |
Boiling point | 60/ 12 mm |
References
Go To: Top, Gas phase thermochemistry 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.
Van-chin-syan, Kochubei, et al., 1996
Van-chin-syan, Yu.Ya.; Kochubei, V.V.; Sergeev, V.V.; Raevskii, Yu.A.; Gerasimchuk, S.I.; Kotovich, Kh.Z.,
Thermodynamic properties of some acids and aldehydes of the acrylic series,
Sov. J. Chem. Phys. (Engl. Transl.), 1996, 70, 1789-1794, In original 1932. [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 σp constants,
J. Org. Chem. USSR (Engl. Transl.), 1976, 12, 1594-1597. [all data]
Graul, Schnute, et al., 1990
Graul, S.T.; Schnute, M.E.; Squires, R.R.,
Gas-Phase Acidities of Carboxylic Acids and Alcohols from Collision-Induced Dissociation of Dimer Cluster Ions,
Int. J. Mass Spectrom. Ion Proc., 1990, 96, 2, 181, https://doi.org/10.1016/0168-1176(90)87028-F
. [all data]
Skinner and Snelson, 1959
Skinner, H.A.; Snelson, A.,
Heats of hydrogenation Part 3.,
Trans. Faraday Soc., 1959, 55, 405-407. [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]
Holmes, Terlouw, et al., 1979
Holmes, J.L.; Terlouw, J.K.; Vijfhuizen, P.C.; A'Campo, C.,
Metastable ion studies XII-Molecular and fragment ion structures for isomeric C4H6O2 acids,
Org. Mass Spectrom., 1979, 14, 204. [all data]
Burgers, Holmes, et al., 1982
Burgers, P.C.; Holmes, J.L.; Lossing, F.P.; Mommers, A.A.; Povel, F.R.; Terlouw, J.K.,
Isomeric and tautomeric [C4H4O]+ ions. Their thermochemistry and collisionally induced fragmentation characteristics,
Can. J. Chem., 1982, 60, 2246. [all data]
Fihtengolts, et al., 1969
Fihtengolts, V.S., et al.,
Atlas of UV Absorption Spectra of Substances Used in Synthetic Rubbers Manufacture, 1969, 13. [all data]
Notes
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
- Symbols used in this document:
AE Appearance energy 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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