Butanedinitrile

• Formula: C₄H₄N₂
• Molecular weight: 80.0880
• IUPAC Standard InChI: InChI=1S/C4H4N2/c5-3-1-2-4-6/h1-2H2 Copy

  
• IUPAC Standard InChIKey: IAHFWCOBPZCAEA-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-61-2
• 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.
• Other names: Succinonitrile; s-Dicyanoethane; Deprelin; Dician; Dinile; Disuxyl; Ethane, 1,2-dicyano-; Ethylene cyanide; Ethylene dicyanide; Evanex; Succinic acid dinitrile; Succinic acid nitrile; Succinic dinitrile; Succinil; Succinodinitrile; Suxil; 1,2-Dicyanoethane; NCCH2CH2CN; USAF A-9442; 1,4-Butanedinitrile; Sukcinonitril; sym-Dicyanoethane; NSC 4852
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
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Gas 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

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 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

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
B - John E. Bartmess

View reactions leading to C₄H₄N₂⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

IR Spectrum

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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: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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.

Rapport, Westrum, et al., 1971
Rapport, N.J.; Westrum, E.F., Jr.; Andrews, J.T.S., Enthalpies of formation for globular molecules. III. Succinonitrile and triethylenediamine, J. Am. Chem. Soc., 1971, 93, 4363-4365. [all data]

Wulff and Westrum, 1963
Wulff, C.A.; Westrum, E.F., Jr., Heat capacities and thermodynamic properties of globular molecules. VI. Succinonitrile, J. Phys. Chem., 1963, 67, 2376-2381. [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]

Anonymous, 1988
Anonymous, X., , NBS Spec. Publ. (U. S.) 260, 1988. [all data]

Marsh, 1987
Marsh, K.N., Recommended Reference Materials for the Realization of Physicochemical Properties, Blackwell Sci. Pub., Oxford, 1987. [all data]

Mangum and El-Sabban, 1985
Mangum, B.W.; El-Sabban, S., SRM 1970: Succinotitrile Triple-Point Standard - A Temperature Reference Standard Near 58.08 C, J. Res. Natl. Bur. Stand. (U. S.), 1985, 90, 359. [all data]

Wulff and Westrum, 1963, 2
Wulff, C.A.; Westrum, E.F., Heat capacities and thermodynamic properties of globular molecules: vi succinonitrile, J. Phys. Chem., 1963, 67, 2376-81. [all data]

Woodman, Murbach, et al., 1960
Woodman, A.L.; Murbach, W.J.; Kaufman, M.H., Vapor pressure and viscosity relationships for a homologous series of α,omega-dinitriles, Russ. J. Phys. Chem. (Engl. Transl.), 1960, 64, 658-660. [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., , Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [all data]

Westrum, Rapport, et al., 1971
Westrum, Edgar F.; Rapport, Naomi J.; Andrews, John T.S., Enthalpies of formation for globular molecules III. Succinonitrile and triethylenediamine, J. Am. Chem. Soc., 1971, 93, 18, 4363-4365, https://doi.org/10.1021/ja00747a005 . [all data]

Stull, Westrum, et al., 1969
Stull, D.R.; Westrum, E.F., Jr.; Sinke, G.C., The Chemical Thermodyanmics of Organic Compounds, John Wiley & Sons Inc., New York, 1969, 865. [all data]

Rai, Singh, et al., 1987
Rai, U.S.; Singh, O.P.; Singh, N.B., Some thermodynamic aspects of organic eutectics, succinonitrile-phenanthrene system, Indian J. Chem., 1987, 26A, 947-949. [all data]

Rai and Reddi, 2009
Rai, R.N.; Reddi, R.S.B., Thermal, solid--liquid equilibrium, crystallization, and microstructural studies of organic monotectic alloy: 4,4´-Dibromobiphenyl--succinonitrile, Thermochimica Acta, 2009, 496, 1-2, 13-17, https://doi.org/10.1016/j.tca.2009.06.012 . [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]

Desfrancois, Bouteiller, et al., 2004
Desfrancois, C.; Bouteiller, Y.; Schermann, J.P.; Radisic, D.; Stokes, S.T.; Bowen, K.H.; Hammer, N.I.; Compto, Long-range electron binding to quadrupolar molecules, Phys. Rev. Lett., 2004, 92, 8, 840-850, https://doi.org/10.1103/PhysRevLett.92.083003 . [all data]

Chess, Lapp, et al., 1982
Chess, E.K.; Lapp, R.L.; Gross, M.L., The question of tautomerism of alkylnitrile and isonitrile radical cations, Org. Mass Spectrom., 1982, 17, 475. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  EA	Electron affinity
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

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