Benzyl nitrile

• Formula: C₈H₇N
• Molecular weight: 117.1479
• IUPAC Standard InChI: InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 Copy

  
• IUPAC Standard InChIKey: SUSQOBVLVYHIEX-UHFFFAOYSA-N Copy
• CAS Registry Number: 140-29-4
• 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: Benzyl cyanide; Benzeneacetonitrile; Acetonitrile, phenyl-; α-Cyanotoluene; α-Tolunitrile; ω-Cyanotoluene; Phenylacetonitrile; 2-Phenylacetonitrile; Toluene, α-cyano-; USAF KF-21; (Cyanomethyl)benzene; Phenyl acetyl nitrile; UN 2470; Phenacetonitrile; 2-Phenylethanenitrile; NSC 118418
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Gas phase ion energetics data

Go To: Top, Phase change 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
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C₈H₇N⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₈H₆N^- +  =

By formula: C₈H₆N^- + H⁺ = C₈H₇N

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.

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

Verevkin, 2000
Verevkin, Sergey P., Strain effects in phenyl substituted methanes. Geminal interactions between phenyl and electron-withdrawing cyano substituent in benzylcyanides, The Journal of Chemical Thermodynamics, 2000, 32, 2, 207-215, https://doi.org/10.1006/jcht.1999.0591 . [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]

Stull, 1947
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]

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]

Selim, Rabbih, et al., 1987
Selim, E.T.; Rabbih, M.A.; Fahmey, M.A., M and [M-1]⁺ ions formed for benzyl alcohol, benzyl amine and benzyl cyanide, Org. Mass Spectrom., 1987, 22, 381. [all data]

Van Der Greef, Molenaar-Langeveld, et al., 1979
Van Der Greef, J.; Molenaar-Langeveld, T.A.; Nibbering, N.M.M., The elimination of HCN (or HNC) from the molecular ions of some isomeric C₈H₇N compounds, studied by field ionization kinetic and kinetic energy release measurements, Int. J. Mass Spectrom. Ion Phys., 1979, 29, 11. [all data]

Buchs, 1970
Buchs, A., Etude par spectrometrie de masse de l'ionisation de benzonitriles, de phenylacetonitriles et de N,N-dimethylanilines substitues, Helv. Chim. Acta, 1970, 53, 2026. [all data]

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH₂-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]

Selim, Rabbih, et al., 1989
Selim, E.T.M.; Rabbih, M.A.; Fahmey Ahmad, M.A.; Shalbi, A.S., Energetic study of [C₅H₃]⁺ fragment ion produced from some benzyl derivatives, Arab Gulf J. Sci. Res., 1989, 7, 53. [all data]

Selim, Rabbih, et al., 1987, 2
Selim, E.T.; Rabbih, M.A.; Rezk, A.M.H.; Fahmey, M.A., Energetics of [C₇H₆]⁺ fragment ion using electron impact technique, Indian J. Pure Appl. Phys., 1987, 25, 451. [all data]

Selim, Rabbih, et al., 1987, 3
Selim, E.T.M.; Rabbih, M.A.; Fahmey, M.A., A mass spectrometric study of [C₇H₇]⁺ and [C₆H₇]⁺ fragment ions obtained from benzyl alcohol, benzyl amine and benzyl cyanide, Egypt. J. Phys., 1987, 18, 37. [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy 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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.