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:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Reaction 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:
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

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

Gas Phase Spectrum

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Additional Data

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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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.

Harland, 1986
Harland, P.W., Appearance energies and enthalpies of formation from ionization of cyanoacetylene by "Monochromatic" electron impact, Int. J. Mass Spectrom. Ion Processes, 1986, 70, 231-236. [all data]

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]

Do and Raulin, 1992
Do, L.; Raulin, F., Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column, J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R . [all data]

Do and Raulin, 1989
Do, L.; Raulin, F., Gas chromatography of Titan's atmosphere. I. Analysis of low-molecular-weight hydrocarbons and nitriles with a PoraPLOT Q porous polymer coated open-tubular capillary column, J. Chromatogr., 1989, 481, 45-54, https://doi.org/10.1016/S0021-9673(01)96751-2 . [all data]

Notes

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• Symbols used in this document:
  

  T	Temperature
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  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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