Propanedioic acid
- Formula: C3H4O4
- Molecular weight: 104.0615
- IUPAC Standard InChIKey: OFOBLEOULBTSOW-UHFFFAOYSA-N
- CAS Registry Number: 141-82-2
- 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. - Isotopologues:
- Other names: Malonic acid; Carboxyacetic acid; Dicarboxymethane; Methanedicarboxylic acid; CH2(COOH)2; USAF EK-695; Kyselina malonova; Methanedicarbonic acid; NSC 8124
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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°solid | -891.1 ± 0.4 | kJ/mol | Ccb | Wilhoit and Shiao, 1964 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -861.15 ± 0.63 | kJ/mol | Ccb | Wilhoit and Shiao, 1964 | Corresponding ΔfHºsolid = -891.02 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -861.57 ± 0.63 | kJ/mol | Ccb | Verkade, Hartman, et al., 1926 | Reanalyzed by Cox and Pilcher, 1970, Original value = -864.0 kJ/mol; See Verkade, Hartman, et al., 1924; Corresponding ΔfHºsolid = -890.61 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 149.00 | J/mol*K | N/A | Fukai, Matsuo, et al., 1991 | crystaline, II phase; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
127.63 | 298.15 | Fukai, Matsuo, et al., 1991 | crystaline, II phase; T = 10 to 370 K.; 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
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 |
---|---|---|---|---|---|
Tfus | 408.05 | K | N/A | Wilhoit and Shiao, 1964, 2 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 407.9 | K | N/A | Wilhoit and Shiao, 1964, 2 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 111.4 ± 0.7 | kJ/mol | N/A | Ribeiro da Silva, Monte, et al., 1999 | AC |
ΔsubH° | 105.1 ± 0.8 | kJ/mol | C | Al-Takhin, Pilcher, et al., 1983 | ALS |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
108.9 ± 0.7 | 348. | ME | Ribeiro da Silva, Monte, et al., 1999 | Based on data from 339. to 357. K.; AC |
72.7 | 306. | A | Stephenson and Malanowski, 1987 | Based on data from 291. to 320. K. See also Granovskaya, 1947.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
23.1 | 407.5 | Hansen and Beyer, 2004 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.01480 | 47.3 | crystaline, III | crystaline, II | Fukai, Matsuo, et al., 1991 | DH |
1.837 | 352.2 | crystaline, II | crystaline, I | Fukai, Matsuo, et al., 1991 | DH |
1.600 | 351.2 | crystaline, II | crystaline, I | Petropavlov, Tsygankova, et al., 1988 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.313 | 47.3 | crystaline, III | crystaline, II | Fukai, Matsuo, et al., 1991 | DH |
5.217 | 352.2 | crystaline, II | crystaline, I | Fukai, Matsuo, et al., 1991 | DH |
4.6 | 351.2 | crystaline, II | crystaline, I | Petropavlov, Tsygankova, et al., 1988 | 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
C3H3O4- + =
By formula: C3H3O4- + H+ = C3H4O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1341. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1318. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase; B |
By formula: C3H4O4 + Br2 = HBr + C3H3BrO4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -66.0 ± 2.9 | kJ/mol | Cm | Koros, Orban, et al., 1979 | liquid phase; solvent: Sulfuric acid (1M); Bromination; ALS |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby
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 | Japan AIST/NIMC Database- Spectrum MS-NW-2634 |
NIST MS number | 229341 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wilhoit and Shiao, 1964
Wilhoit, R.C.; Shiao, D.,
Thermochemistry of biologically important compounds. Heats of combustion of solid organic acids.,
J. Chem. Eng. Data, 1964, 9, 595-599. [all data]
Verkade, Hartman, et al., 1926
Verkade, P.E.; Hartman, H.; Coops, J.,
Calorimetric researches. X. Heats of combustion of successive terms of homologous series: dicarboxylic acids of the oxalic acid series,
Rec. Trav. Chim. Pays/Bas, 1926, 45, 373-393. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Verkade, Hartman, et al., 1924
Verkade, P.E.; Hartman, H.; Coops, J., Jr.,
Chemistry - The molecular heat of combustion of successive terms of homologous series,
Kom. Med. Akad. Ueknschap. Proc., 1924, 27, 859-866. [all data]
Fukai, Matsuo, et al., 1991
Fukai, M.; Matsuo, T.; Suga, H.,
Thermodynamic properties of phase transitions in malonic acid and its deuterated analog,
Thermochim. Acta, 1991, 183, 215-243. [all data]
Wilhoit and Shiao, 1964, 2
Wilhoit, R.C.; Shiao, D.,
Thermochemistry of Biologically Important Compounds. Heats of Combustion of Solid Organic Acids,
J. Chem. Eng. Data, 1964, 9, 595. [all data]
Ribeiro da Silva, Monte, et al., 1999
Ribeiro da Silva, Manuel A.V.; Monte, Manuel J.S.; Ribeiro, José R.,
Vapour pressures and the enthalpies and entropies of sublimation of five dicarboxylic acids,
The Journal of Chemical Thermodynamics, 1999, 31, 8, 1093-1107, https://doi.org/10.1006/jcht.1999.0522
. [all data]
Al-Takhin, Pilcher, et al., 1983
Al-Takhin, G.; Pilcher, G.; Bickerton, J.,
Standard enthalpies of formation of diamine(dicarboxylato)platinum(II) complexes and of bis(pentane-2,4-dionato)platinum(II): the mean Pt-O bond dissociation enthalpies,
J. Chem. Soc. Dalton Trans., 1983, 2657-2659. [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]
Granovskaya, 1947
Granovskaya, A.,
Russ. J. Phys. Chem., 1947, 21, 967. [all data]
Hansen and Beyer, 2004
Hansen, Anne R.; Beyer, Keith D.,
Experimentally Determined Thermochemical Properties of the Malonic Acid/Water System: Implications for Atmospheric Aerosols,
J. Phys. Chem. A, 2004, 108, 16, 3457-3466, https://doi.org/10.1021/jp0376166
. [all data]
Petropavlov, Tsygankova, et al., 1988
Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A.,
Microcalorimetric investigation of polymorphic transitions in organic crystals,
Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [all data]
Kumar, Prabhakar, et al., 2005
Kumar, M.R.; Prabhakar, S.; Nagaveni, V.; Vairamani, M.,
Estimation of gas-phase acidities of a series of dicarboxylic acids by the kinetic method,
Rapid Commun. Mass Spectrom., 2005, 19, 8, 1053-1057, https://doi.org/10.1002/rcm.1888
. [all data]
Koros, Orban, et al., 1979
Koros, E.; Orban, M.; Nagy, Z.,
Calorimetric studies on the Belousov-Zhabotinsky oscillatory chemical reaction,
Acta Chim. Acad. Sci. Hung., 1979, 100, 449-461. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tfus Fusion (melting) point ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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