2-Propenenitrile

• Formula: C₃H₃N
• Molecular weight: 53.0626
• IUPAC Standard InChI: InChI=1S/C3H3N/c1-2-3-4/h2H,1H2 Copy

  
• IUPAC Standard InChIKey: NLHHRLWOUZZQLW-UHFFFAOYSA-N Copy
• CAS Registry Number: 107-13-1
• 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: Acrylonitrile; Acrylon; Carbacryl; Cyanoethylene; Fumigrain; Propenenitrile; Ventox; Vinyl cyanide; VCN; CH2CHCN; Acritet; Acrylnitril; Acrylonitrile monomer; Akrylonitryl; Cianuro di vinile; Cyanure de vinyle; ENT 54; Miller's fumigrain; Nitrile acrilico; Nitrile acrylique; TL 314; Akrylonitril; Rcra waste number U009; UN 1093; Vinylkyanid; Cyanoethene; Propenitrile; Propenonitrile; NSC 6362
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction 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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C₃H₂N^- +  =

By formula: C₃H₂N^- + H⁺ = C₃H₃N

 +  = C₂₃H₁₇NO

By formula: C₃H₃N + C₂₀H₁₄O = C₂₃H₁₇NO

(CAS Reg. No. 42117-12-4 • 4294967295) +  = CAS Reg. No. 42117-12-4

By formula: (CAS Reg. No. 42117-12-4 • 4294967295C₃H₃N) + C₃H₃N = CAS Reg. No. 42117-12-4

C₃H₄N⁺ +  = (C₃H₄N⁺ • )

By formula: C₃H₄N⁺ + C₃H₃N = (C₃H₄N⁺ • C₃H₃N)

 + 2 = 2 + ammonium sulphide

By formula: C₆H₈N₂S + 2H₃N = 2C₃H₃N + ammonium sulphide

(CAS Reg. No. 180058-39-3 • 4294967295) +  = CAS Reg. No. 180058-39-3

By formula: (CAS Reg. No. 180058-39-3 • 4294967295C₃H₃N) + C₃H₃N = CAS Reg. No. 180058-39-3

2 + ammonium sulphide =  + 2

By formula: 2C₃H₃N + ammonium sulphide = C₆H₈N₂S + 2H₃N

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₃H₃N⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₃H₂N^- +  =

By formula: C₃H₂N^- + H⁺ = C₃H₃N

References

Go To: Top, Phase change data, 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.

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [all data]

Timmermans, 1922
Timmermans, J., Investigation of the Freezing Point of Organic Substances VII, Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]

Finke, Messerly, et al., 1972
Finke, H.L.; Messerly, J.F.; Todd, S.S., Thermodynamic properties of acrylonitrile, 1-aminopropane, 2-aminopropane, and 2-methyl-2-aminopropane, J. Chem. Thermodyn., 1972, 4, 359. [all data]

Wilson, Wilson, et al., 1996
Wilson, L.C.; Wilson, H.L.; Wilding, W.V.; Wilson, G.M., Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method, J. Chem. Eng. Data, 1996, 41, 1252-4. [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]

Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Davis and Wiedeman, 1945
Davis, H.S.; Wiedeman, O.F., Physical properties of acrylonitrile, Ind. Chim. Belge, 1945, 37, 482-485. [all data]

Gubkov, Fermor, et al., 1964
Gubkov, A.N.; Fermor, N.A.; Smirnov, N.I., Zh. Prikl. Khim. (S.-Peterburg), 1964, 37, 2204. [all data]

Sevrugova, Sokorskii, et al., 1964
Sevrugova, N.N.; Sokorskii, V.A.; Zhavoronkov, N.M., Zh. Prikl. Khim. (Leningrad), 1964, 37, 1989. [all data]

Gubkov, Fermor, et al., 1964, 2
Gubkov, A.N.; Fermor, N.A.; Smirnov, N.I., Vapor Pressure of Mono-Poly Systems, Zh. Prikl. Khim. (Leningrad), 1964, 37, 2204-2210. [all data]

Sevrugova, Sokorskii, et al., 1964, 2
Sevrugova, N.N.; Sokorskii, V.A.; Zhavoronkov, N.M., Phase of Equilibrium for Mixtures Acrylonitrile-Acetonitrile, Zh. Prikl. Khim. (Leningrad), 1964, 37, 9, 1989-1993. [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]

Finke, Messerly, et al., 1972, 2
Finke, H.L.; Messerly, J.F.; Todd, S.S., Thermodynamic properties of acrylonitrile, 1-aminopropane, 2-aminopropane, and 2-methyl-2-aminopropane, J. Chem. Thermodynam., 1972, 4, 359-374. [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]

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]

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]

Kiselev, Ustyugov, et al., 1977
Kiselev, V.D.; Ustyugov, A.N.; Breus, I.P.; Konovalov, A.I., Kinetic and thermochemical study of the Diels-Alder reaction, Dokl. Phys. Chem. (Engl. Transl.), 1977, 234, 320-322, In original 1089. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Meot-Ner (Mautner) and Sieck, 1991
Meot-Ner (Mautner), M.; Sieck, L.W., Proton affinity ladders from variable-temperature equilibrium measurements. 1. A reevaluation of the upper proton affinity range, J. Am. Chem. Soc., 1991, 113, 12, 4448, https://doi.org/10.1021/ja00012a012 . [all data]

Gladstone and Chang, 1966
Gladstone, S.; Chang, H.Y., Determination of the standard heat of formation of 3,3'-thiodipropionitrile, J. Chem. Eng. Data, 1966, 11, 238-239. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

Suess, Liu, et al., 2003
Suess, L.; Liu, Y.; Parthasarathy, R.; Dunning, F.B., Dipole-bound negative ions: Collisional destruction and blackbody-radiation-induced photodetachment, J. Chem. Phys., 2003, 119, 24, 12890-12894, https://doi.org/10.1063/1.1628215 . [all data]

Desfrancois, Abdoul-Carime, et al., 1994
Desfrancois, C.; Abdoul-Carime, H.; Khelifa, N.; Schermann, J.P., Fork 1/r to 1/r2 Potentials: Electron Exchange between Rydberg Atoms and Polar Molecules, Phys. Rev. Lett., 1994, 73, 18, 2436, https://doi.org/10.1103/PhysRevLett.73.2436 . [all data]

Ohno, Matumoto, et al., 1984
Ohno, K.; Matumoto, S.; Imai, K.; Haraa, Y., Penning ionization electron spectroscopy of nitriles, J. Phys. Chem., 1984, 88, 206. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Lake and Thompson, 1970
Lake, R.F.; Thompson, H., The photoelectron spectra of some molecules containing the C N group, Proc. Roy. Soc. (London), 1970, A317, 187. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]

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Houk, K.N.; Munchausen, L.L., Ionization potentials, electron affinities, reactivities of cyanoalkenes related electron-deficient alkenes. A frontier molecular orbital treatment of cyanoalkene reactivities in cycloaddition, electrophilic, nucleophilic, and radical reactions., J. Am. Chem. Soc., 1976, 98, 937. [all data]

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Momigny, J.; Urbain, J.; Wankenne, H., Les effets de l'impact electronique sur la pyridine et les diazines isomeres, Bull. Soc. Roy. Sci. Liege, 1965, 34, 337. [all data]

Chelobov, Dubov, et al., 1969
Chelobov, F.N.; Dubov, S.S.; Tikhomirov, M.V.; Dobrovitskii, M.I.; Gitel', P.O.; Rozenshtein, S.M., Processes in fluoroacrylonitriles under electron impact, Zh. Fiz. Khim., 1969, 43, 33, In original 15. [all data]

Notes

Go To: Top, Phase change data, 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
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction 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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