2-Butynedinitrile

• Formula: C₄N₂
• Molecular weight: 76.0562
• IUPAC Standard InChI: InChI=1S/C4N2/c5-3-1-2-4-6 Copy

  
• IUPAC Standard InChIKey: ZEHZNAXXOOYTJM-UHFFFAOYSA-N Copy
• CAS Registry Number: 1071-98-3
• 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: Acetylenedicarbonitrile; Dicyanoacetylene; 1,2-Dicyanoacetylene; NCC≡CCN; Dicyanoethyne; Sous-azote de carbone; C4N2
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Enthalpy of sublimation

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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, 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.

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]

Armstrong and Marantz, 1963
Armstrong, G.T.; Marantz, S., The heat of combustion of dicyanoacetylene [Correction Ref. 60ARM/MAR], J. Phys. Chem., 1963, 67, 2888. [all data]

Saggiomo, 1957
Saggiomo, A.J., The dinitriles of acetylenedicarboxylic and polyacetylenedicarboxylic acids. I. Dicyanoacetylene and dicycanodiacetylene, J. Org. Chem., 1957, 22, 1171. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

SAGGIOMO, 1957
SAGGIOMO, ANDREW J., The Dinitriles of Acetylenedicarboxylic and Polyacetylenedicarboxylic Acids. ¹ I. ² Dicyanoacetylene and Dicyanodiacetylene, J. Org. Chem., 1957, 22, 10, 1171-1175, https://doi.org/10.1021/jo01361a009 . [all data]

Govers, 1975
Govers, H.A.J., Derivation of carbon--nitrogen, hydrogen--nitrogen and nitrogen--nitrogen non-bonded potential parameters in molecular crystals, Acta Crystallogr Sect A Cryst Phys Diffr Theor Gen Crystallogr', 1975, 31, 3, 380-385, https://doi.org/10.1107/S0567739475000800 . [all data]

Maier, Misev, et al., 1982
Maier, J.P.; Misev, L.; Thommen, F., Dicyanoacetylene cation. Laser-induced fluorescence and photoelectron-photon coincidence studies, J. Phys. Chem., 1982, 86, 514. [all data]

Baker and Turner, 1968
Baker, C.; Turner, D.W., High resolution molecular photoelectron spectroscopy. III.Acetylenes and azaacetylenes, Proc. Roy. Soc. (London), 1968, A308, 19. [all data]

Dibeler, Reese, et al., 1961
Dibeler, V.H.; Reese, R.M.; Franklin, J.L., Mass spectrometric study of cyanogen and cyanoacetylenes, J. Am. Chem. Soc., 1961, 83, 1813. [all data]

Asbrink, Von Niessen, et al., 1980
Asbrink, L.; Von Niessen, W.; Bieri, G., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1980, 21, 93. [all data]

Bieri, Heilbronner, et al., 1979
Bieri, G.; Heilbronner, E.; Hornung, V.; Kloster-Jensen, E.; Maier, J.P.; Thommen, F.; von Niessen, W., Electronic states of substituted haloacetylene and cyanoacetylene radical cations, Chem. Phys., 1979, 36, 1. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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