Acetic acid, cyano-

• Formula: C₃H₃NO₂
• Molecular weight: 85.0614
• IUPAC Standard InChI: InChI=1S/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6) Copy

  
• IUPAC Standard InChIKey: MLIREBYILWEBDM-UHFFFAOYSA-N Copy
• CAS Registry Number: 372-09-8
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Cyanoacetic acid; Malonic mononitrile; Monocyanoacetic acid; NCCH2COOH; 2-Cyanoacetic acid; Acide cyanacetique; USAF KF-17; Cyanessigsaeure; Kyselina kyanoctova; Cyanoethanoic acid; NSC 5571
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• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change 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

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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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C₃H₂NO₂^- +  =

By formula: C₃H₂NO₂^- + H⁺ = C₃H₃NO₂

 +  =  + 

By formula: C₄H₅NO₂ + H₂O = C₃H₃NO₂ + CH₄O

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 by: John E. Bartmess

De-protonation reactions

C₃H₂NO₂^- +  =

By formula: C₃H₂NO₂^- + H⁺ = C₃H₃NO₂

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Guinchant, 1918
Guinchant, M.J., Etude sur la fonction acide dans les derives metheniques et methiniques, Ann. Chem., 1918, 10, 30-84. [all data]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A., Effect of the acyl substituent on the equilibrium constant for hydration of esters, Can. J. Chem., 1980, 58, 1281-1294. [all data]

Notes

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• Symbols used in this document:
  

  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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