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:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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

Go To: Top, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₃H₃O₄^- +  =

By formula: C₃H₃O₄^- + H⁺ = C₃H₄O₄

IR Spectrum

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

• SOLID (SPLIT MULL, FLUOROLUBE FOR 3800-1333 AND NUJOL FOR 1333-450 CM ^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby

• solid; Bruker Tensor 37 FTIR; 0.96450084 cm^-1 resolution

Mass spectrum (electron ionization)

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References, Notes

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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

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

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, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.