Propanedinitrile

• Formula: C₃H₂N₂
• Molecular weight: 66.0614
• IUPAC Standard InChI: InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 Copy

  
• IUPAC Standard InChIKey: CUONGYYJJVDODC-UHFFFAOYSA-N Copy
• CAS Registry Number: 109-77-3
• 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: Malononitrile; Cyanoacetonitrile; Dicyanomethane; Malonic acid dinitrile; Malonodinitrile; Methane, dicyano-; Methylene cyanide; Methylenedinitrile; CH2(CN)2; Malonitrile; Malonic dinitrile; Nitril kyseliny malonove; USAF A-4600; Dwumetylosulfotlenku; Rcra waste number U149; UN 2647; USAF KF-19; NSC 3769
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• Information on this page:
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
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Gas phase ion energetics data

Go To: Top, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₃HN₂^- +  =

By formula: C₃HN₂^- + H⁺ = C₃H₂N₂

Mass spectrum (electron ionization)

Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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

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Additional Data

Gas Chromatography

Go To: Top, Gas phase ion energetics data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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References

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

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

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Molder, Pikver, et al., 1983
Molder, U.H.; Pikver, R.J.; Koppel, I.A., Photoelectron spectra of molecules. 3. Nitriles, Org. React. Tartu, 1983, 20, 230. [all data]

Stafast and Bock, 1973
Stafast, H.; Bock, H., Photoelectron spectra molecular properties. XVII. Hyperconjugation in dicyanomethane and 2,2-dicyano propane, Z. Naturforsch. B:, 1973, 28, 746. [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Taft, Abboud, et al., 1988
Taft, R.W.; Abboud, J.L.M.; Anvia, F.; Berthelot, M.; Fujio, M.; Gal, J.-F.; Headley, A.D.; Henderson, W.G., Regarding the Inherent Dependence of Resonance Effects of Strongly Conjugated Substituents on Electron Demand, J. Am. Chem. Soc., 1988, 110, 6, 1797, https://doi.org/10.1021/ja00214a023 . [all data]

Juvancz, Cserháti, et al., 1994
Juvancz, Z.; Cserháti, T.; Markides, K.E.; Bradshaw, J.S.; Lee, M.L., Characterization of some new polysiloxane stationary phases by principal component analysis, Chromatographia, 1994, 38, 3/4, 227-231, https://doi.org/10.1007/BF02290341 . [all data]

Notes

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

• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  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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