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 | -367.3 ± 2.4 | kJ/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | ALS |
ΔfH°gas | -372.2 | kJ/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 |
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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -414.8 ± 2.3 | kJ/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | ALS |
ΔfH°liquid | -419.7 ± 0.4 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1976 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2016.7 ± 2.2 | kJ/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | Corresponding ΔfHºliquid = -414.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -2012. ± 0.4 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1976 | Corresponding ΔfHºliquid = -419.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
159.7 | 298.15 | Karabaev, Abduzhaminov, et al., 1985 | T = 287 to 350 K. Equation only. Cp (J/kg*K) = -551.8 + 8.0712 T. Cp data calculated from equation.; DH |
159.7 | 298.15 | Karabaev, Saidov, et al., 1985 | T = 90 to 350 K. Cp(c) = 244.98 + 4.92T J/kg*K (95 to 287.5 K); Cp(liq) = -551.47 + 8.07T J/kg*K (287.5 to 350 K). Cp data calculated from equation.; DH |
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 435.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 288. ± 1. | K | AVG | N/A | Average of 5 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 638.4 | K | N/A | D'Souza and Teja, 1987 | Uncertainty assigned by TRC = 3. K; Ambrose's procedure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 49.0521 | bar | N/A | D'Souza and Teja, 1987 | Uncertainty assigned by TRC = 1.00 bar; Ambrose's procedure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 47.5 ± 0.4 | kJ/mol | C | Van-chin-syan, Kochubei, et al., 1996 | ALS |
ΔvapH° | 47.5 | kJ/mol | N/A | Van-chin-syan, Kochubei, et al., 1996 | DRB |
ΔvapH° | 47.5 ± 0.4 | kJ/mol | C | Van-Chin-Syan, Kochubei, et al., 1996 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
53.9 | 336. | A | Stephenson and Malanowski, 1987 | Based on data from 321. to 435. K.; AC |
51.6 | 313. | A | Stephenson and Malanowski, 1987 | Based on data from 298. to 434. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
298.7 to 434. | 5.37325 | 2094.201 | -44.514 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.0625 | 287.5 | Karabaev, Abduzhaminov, et al., 1985, 2 | DH |
8.06 | 287.5 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
28.04 | 287.5 | Karabaev, Abduzhaminov, et al., 1985, 2 | DH |
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° | 1440. ± 12. | kJ/mol | G+TS | Graul, Schnute, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1410. ± 12. | kJ/mol | CIDC | Graul, Schnute, et al., 1990 | gas phase; B |
By formula: H2 + C4H6O2 = C4H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -118. ± 1. | kJ/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) | 816.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 785.7 | kJ/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° | 1440. ± 12. | kJ/mol | G+TS | Graul, Schnute, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1410. ± 12. | kJ/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
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 | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 291422 |
Gas Chromatography
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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
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 711. | Meynier, Novelli, et al., 1999 | 30. m/0.32 mm/1. μm, 40. C @ 5. min, 3. K/min; Tend: 200. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]
Karabaev, Abduzhaminov, et al., 1985
Karabaev, M.; Abduzhaminov, T.P.; Saidov, A.A.; Igamberdyev, Kh.T.,
Thermophysical properties of liquid methacrylic acid and its simple esters, Izv. Akad. Nauk Uzb. SSR,
Ser. Fiz.-Mat. Nauk, 1985, (4), 71-74. [all data]
Karabaev, Saidov, et al., 1985
Karabaev, M.; Saidov, A.A.; Abduzhaminov, T.P.; Kenisarin, M.M.,
Heat capacity and molecular kinetic processes of condensed phase acrylates and methacrylates, Izv. Akad. Nauk UzSSR,
Ser. Fiz.-Math., 1985, (6), 51-54. [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]
D'Souza and Teja, 1987
D'Souza, R.; Teja, A.S.,
The prediction of the vapor pressures of carboxylic acids,
Chem. Eng. Commun., 1987, 61, 13. [all data]
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 acrylic-series acids and aldehydes,
Zh. Fiz. Khim., 1996, 70, 11, 1932. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Karabaev, Abduzhaminov, et al., 1985, 2
Karabaev, M.K.; Abduzhaminov, T.P.; Kenisarin, M.M.; Saidov, A.A.,
Thermodynamics of the crystal-liquid phase transition in acrylates and methacrylates, Izv. Akad. Nauk Uzb. SSR,
Ser. Fiz.-Mat. Nauk, 1985, (5), 74-77. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
Meynier, Novelli, et al., 1999
Meynier, A.; Novelli, E.; Chissolinim, R.; Zanardi, E.; Gandemer, G.,
Volatile compounds of commercial Milano salami,
Meat Sci., 1999, 51, 2, 175-183, https://doi.org/10.1016/S0309-1740(98)00122-3
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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