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:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change 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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Condensed phase thermochemistry 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

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

 +  =  + 

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, Condensed phase thermochemistry 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, 595-599. [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]

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, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid 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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