Propiolonitrile

• Formula: C₃HN
• Molecular weight: 51.0467
• IUPAC Standard InChI: InChI=1S/C3HN/c1-2-3-4/h1H Copy

  
• IUPAC Standard InChIKey: LNDJVIYUJOJFSO-UHFFFAOYSA-N Copy
• CAS Registry Number: 1070-71-9
• 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: Cyanoacetylene; HC≡CCN; Cyanaethylene; Cyanoethyne; Propynenitrile; 2-Propynenitrile
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Reaction thermochemistry data

Go To: Top, 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₃HN = (CH₆N⁺ • C₃HN)

Free energy of reaction

C₃N^- +  =

By formula: C₃N^- + H⁺ = C₃HN

(CAS Reg. No. 36259-97-9 • 4294967295) +  = CAS Reg. No. 36259-97-9

By formula: (CAS Reg. No. 36259-97-9 • 4294967295C₃HN) + C₃HN = CAS Reg. No. 36259-97-9

 +  = ( • )

By formula: H₄N⁺ + C₃HN = (H₄N⁺ • C₃HN)

C₃H₂N⁺ +  = (C₃H₂N⁺ • )

By formula: C₃H₂N⁺ + C₃HN = (C₃H₂N⁺ • C₃HN)

 +  = C₂₃H₁₇NO

By formula: C₃HN + C₂₀H₁₄O = C₂₃H₁₇NO

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 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₃HN⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₃N^- +  =

By formula: C₃N^- + H⁺ = C₃HN

References

Go To: Top, Reaction thermochemistry 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.

Speller and Meot-Ner (Mautner), 1985
Speller, C.V.; Meot-Ner (Mautner), M., The Ionic Hydrogen Bond and Ion Solvation. 3. Bonds Involving Cyanides. Correlations with Proton Affinites, J. Phys. Chem., 1985, 81, 24, 5217, https://doi.org/10.1021/j100270a020 . [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]

Graupner, Merrigan, et al., 2006
Graupner, K.; Merrigan, T.L.; Field, T.A.; Youngs, T.G.A.; Marr, P.C., Dissociative Electron Attachment to HCCCN, New J. Phys., 2006, , 117 (2006), 7, 117, https://doi.org/10.1088/1367-2630/8/7/117 . [all data]

Bartmess, 1980
Bartmess, J.E., Solvent effects on ion-molecule reactions. Vinyl anions vs. conjugate addition, J. Am. Chem. Soc., 1980, 102, 2483. [all data]

Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I., Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles, Zh. Org. Khim., 1983, 19, 1431-1435. [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]

Goebbert, Khuseynov, et al., 2010
Goebbert, D.J.; Khuseynov, D.; Sanov, A., Photoelectron Imiaging Spectrum of Cyanovinylidene and Cyanoacetylene anion, J. Phys. Chem. A, 2010, 114, 6, 2259, https://doi.org/10.1021/jp9106102 . [all data]

Heni and Illenberger, 1986
Heni, M.; Illenberger, E., Electron attachment by saturated nitriles. Acrylonitrile (CH₂H₃CN), and benzonitrile (C₆H₅CN), Int. J. Mass Spectrom. Ion Phys., 1986, 73, 127. [all data]

Harland, 1986
Harland, P.W., Appearance energies and enthalpies of formation from ionization of cyanoacetylene by "monochromatic" electron impact, Int. J. Mass Spectrom. Ion Phys., 1986, 70, 231. [all data]

Okabe and Dibeler, 1973
Okabe, H.; Dibeler, V.H., Photon impact studies of C₂HCN and CH₃CN in the vacuum ultraviolet; heats of formation of C₂H and CH₃CN, J. Chem. Phys., 1973, 59, 2430. [all data]

Narayan, 1972
Narayan, B., Spectra and ionization potential of cyanoacetylene, Proc. Indian Acad. Sci. Sect. A, 1972, 75, 92. [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]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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