Propanedioic acid

• Formula: C₃H₄O₄
• Molecular weight: 104.0615
• IUPAC Standard InChI: InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) Copy

  
• IUPAC Standard InChIKey: OFOBLEOULBTSOW-UHFFFAOYSA-N Copy
• 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:
  • [2H2]malonic [2H2]acid
• Other names: Malonic acid; Carboxyacetic acid; Dicarboxymethane; Methanedicarboxylic acid; CH2(COOH)2; USAF EK-695; Kyselina malonova; Methanedicarbonic acid; NSC 8124
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Phase change data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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:
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

Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, 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

C₃H₃O₄^- +  =

By formula: C₃H₃O₄^- + H⁺ = C₃H₄O₄

 +  =  + 

By formula: C₃H₄O₄ + Br₂ = HBr + C₃H₃BrO₄

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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₃H₃O₄^- +  =

By formula: C₃H₃O₄^- + H⁺ = C₃H₄O₄

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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. [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]

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]

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]

Ajo, Ciliberto, et al., 1980
Ajo, D.; Ciliberto, E.; Fragala, I.; Granozzi, G., Lone-pair interactions in the photoelectron spectra of dicarboxylic acids: Malonic acid its α-alkyl derivatives, J. Mol. Struct., 1980, 62, 189. [all data]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  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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