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
  The 3d structure may be viewed using Java or Javascript.
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• 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.

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

Phase change data

Go To: Top, Gas phase 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of fusion

Temperature of phase transition

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Phase change data, 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

References

Go To: Top, Gas phase thermochemistry data, Phase change 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.

Beckhaus, Dogan, et al., 1990
Beckhaus, H.D.; Dogan, B.; Pakusch, J.; Verevkin, S.; Ruechardt, C., Geminal substituent effects. 4. The dependence of the inverse anomeric effect of geminal cyano groups on the structure, Chem. Ber., 1990, 123, 2153-2159. [all data]

Boyd, Guha, et al., 1967
Boyd, R.H.; Guha, K.R.; Wuthrich, R., Thermochemistry of cyanocarbons. II. The heats of combustion of pyridinium dicyanomethylide, malononitrile, and fumaronitrile, J. Phys. Chem., 1967, 71, 2187-2191. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Stephenson, 1994
Stephenson, R.M., Mutual Solubility of Water and Nitriles, J. Chem. Eng. Data, 1994, 39, 225-7. [all data]

Trunel, 1939
Trunel, P., Electric Moments in Several Homologous Series of Organic Compounds, Ann. Chim. (Paris), 1939, 12, 110. [all data]

Van de Vloed, 1939
Van de Vloed, A., Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]

Bruhl, 1895
Bruhl, J.W., Spectrochemistry of Nitrogen-Containing Compounds. I., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1895, 16, 193. [all data]

Girdhar, Westrum, et al., 1968
Girdhar, H.L.; Westrum, E.F.; Wulff, C.A., Thermodynamic properties and third-law cycle for malononitrile., J. Chem. Eng. Data, 1968, 13, 239-42. [all data]

Westrum and Wulff, 1968
Westrum, E.F.; Wulff, C.A., Thermodynamic properties and third-law cycle for malononitrile, J. Chem. Eng. Data, 1968, 13, 239. [all data]

Badea, Blanco, et al., 2007
Badea, Elena; Blanco, Ignazio; Della Gatta, Giuseppe, Fusion and solid-to-solid transitions of a homologous series of alkane-α,ω-dinitriles, The Journal of Chemical Thermodynamics, 2007, 39, 10, 1392-1398, https://doi.org/10.1016/j.jct.2007.03.005 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Wasiutynski, Olejarczyk, et al., 1987
Wasiutynski, T.; Olejarczyk, W.; Sciesinski, J.; Witko, W., Phase transition studies of malononitrile, J. Phys. C: Solid State Phys., 1987, 20, L65-L69. [all data]

Girdhar, Westrum, et al., 1968, 2
Girdhar, H.L.; Westrum, E.F., Jr.; Wulff, C.A., Thermodynamic properties and third-law cycle for malononitrile, J. Chem. Eng. Data, 1968, 13, 239-242. [all data]

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]

Notes

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

• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Ttrs	Temperature of phase transition
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation 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.