Benzonitrile

• Formula: C₇H₅N
• Molecular weight: 103.1213
• IUPAC Standard InChI: InChI=1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H Copy

  
• IUPAC Standard InChIKey: JFDZBHWFFUWGJE-UHFFFAOYSA-N Copy
• CAS Registry Number: 100-47-0
• 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: Benzene, cyano-; Benzoic acid nitrile; Cyanobenzene; Phenyl cyanide; Benzenenitrile; Fenylkyanid; UN 2224
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Henry's Law data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• Options:
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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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - 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 liquid

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

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:
B - John E. Bartmess
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

 +  = ( • )

By formula: Br^- + C₇H₅N = (Br^- • C₇H₅N)

Free energy of reaction

 +  = ( • )

By formula: Cl^- + C₇H₅N = (Cl^- • C₇H₅N)

Free energy of reaction

C₇H₄N^- +  =

By formula: C₇H₄N^- + H⁺ = C₇H₅N

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₇H₅N = (C₆H₇N⁺ • C₇H₅N)

Free energy of reaction

C₁₁H₁₀⁺ +  = (C₁₁H₁₀⁺ • )

By formula: C₁₁H₁₀⁺ + C₇H₅N = (C₁₁H₁₀⁺ • C₇H₅N)

Free energy of reaction

 +  = ( • )

By formula: NO^- + C₇H₅N = (NO^- • C₇H₅N)

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₇H₅N = (CH₆N⁺ • C₇H₅N)

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
LL - Sharon G. Lias and Joel F. Liebman
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 C₇H₅N⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₇H₄N^- +  =

By formula: C₇H₄N^- + H⁺ = C₇H₅N

Ion clustering 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:
B - John E. Bartmess
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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: Br^- + C₇H₅N = (Br^- • C₇H₅N)

Free energy of reaction

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₇H₅N = (CH₆N⁺ • C₇H₅N)

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₇H₅N = (C₆H₇N⁺ • C₇H₅N)

Free energy of reaction

C₁₁H₁₀⁺ +  = (C₁₁H₁₀⁺ • )

By formula: C₁₁H₁₀⁺ + C₇H₅N = (C₁₁H₁₀⁺ • C₇H₅N)

Free energy of reaction

 +  = ( • )

By formula: Cl^- + C₇H₅N = (Cl^- • C₇H₅N)

Free energy of reaction

 +  = ( • )

By formula: NO^- + C₇H₅N = (NO^- • C₇H₅N)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID; PERKIN-ELMER; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, 10% IN CCl4 FOR 650-240 CM^-1) VERSUS SOLVENT; DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION (10.14% IN CCl4 FOR 3800-1300, 10.05% IN CS2 FOR 1300-600, AND 10.14% IN CS2 FOR 600-250 CM^-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas; HP-GC/MS/IRD

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

UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

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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Kovats' RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Lebedev, Bykova, et al., 1985
Lebedev, B.V.; Bykova, T.A.; Kiparisova, E.G.; Chernomordik, Yu.A.; Kurapov, A.S.; Sergeev, V.A., Thermodynamic study of benzonitrile, the process of its cocyclotrimerization with phenylacetylene, and the 2,4,6-triphenylpyridine that is formed, in the interval 0-330°K, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985, 274-279. [all data]

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Lebedev, B.V.; Bykova, T.A.; Kiparisova, E.G.; Pankratov, V.A.; Mitina, L.M.; Korshak, V.V., Thermodynamics of benzonitrile, of its cyclotrimerization process, and of the triphenyl-s-triazine formed in the range 0-300°K, J. Gen. Chem. USSR, 1984, 54, 1209-1214. [all data]

Lebedev, Bykova, et al., 1985, 2
Lebedev, B.V.; Bykova, T.A.; Kiparisova, Y.G.; Chernomordik, Yu.A.; Kurapov, A.S.; Sergeev, V.A., Thermodynamic study of benzonitrile, the process of its cocyclotrimerization with phenylacetylene, and the resulting 2,4,6-triphenylpyridine at 0-300 K, Izv. Akad. Nauk SSSR, Ser. Khim., 1985, (2), 301-306. [all data]

Lebedev, Bykova, et al., 1984, 2
Lebedev, B.V.; Bykova, T.A.; Kiparisova, Y.G.; Pankratov, V.A.; Mitina, L.M.; Korshak, V.V., Thermodynamics of benzonitrile, of its cyclotrimerization process, and of the triphenyl-s-triazine formed in the range 0-330°K, Zhur. Obsch. Khim., 1984, 54, 1352-1358. [all data]

Bykova, Lebedev, et al., 1983
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Mirzaliev, Shakhuradov, et al., 1987
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Bykova, T.A.; Lebedev, B.V.; Tarasov, E.N., Thermodynamics of benzonitrile in the range 0-330 K, Termodin. Org. Soedin., 1983, 48-52. [all data]

Steele, Chirico, et al., 1994
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Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

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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]

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Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

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Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

Meot-ner and Kafafi, 1988
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Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

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El-Shall, M.S.; Meot-Ner (Mautner), M., Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors, J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017 . [all data]

Reents and Freiser, 1981
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Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

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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]

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Araki and Sato, 1996
Araki, M.; Sato, S.-i., Two-color zero kinetic energy photoelectron spectra of benzonitrile and its van der Waals complexes with argon. Adiabatic ionization potentials and cation vibrational frequencies, J. Phys. Chem., 1996, 100, 10542. [all data]

Klasinc, Kovac, et al., 1983
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Baldwin, 1979
Baldwin, M.A., Appearance energies and the kinetic shift. Loss of HCN from the benzonitrile molecular ion, Org. Mass Spectrom., 1979, 14, 601. [all data]

Behan, Johnstone, et al., 1976
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McLafferty, Bente, et al., 1973
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Palmer, Moyes, et al., 1980
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Hirt, R.C.; King, F.T., Search for weak absorption bands in benzonitrile in the near ultraviolet, J. Chem. Phys., 1952, 20, 1821-1822. [all data]

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Brown, I.; Chapman, I.L.; Nicholson, G.J., Gas chromatography of polar solutes in electron acceptor stationary phases, Aust. J. Chem., 1968, 21, 5, 1125-1141, https://doi.org/10.1071/CH9681125 . [all data]

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Evans, M.B.; Smith, J.F., Gas chromatography in qualitative analysis. IV. An investigation of the changes in relative rentention data accompanying the oxidation of apolar stationary phases, J. Chromatogr., 1967, 28, 277-284, https://doi.org/10.1016/S0021-9673(01)85968-9 . [all data]

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Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  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
  ρc	Critical density

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