Benzonitrile, 4-methyl-

• Formula: C₈H₇N
• Molecular weight: 117.1479
• IUPAC Standard InChI: InChI=1S/C8H7N/c1-7-2-4-8(6-9)5-3-7/h2-5H,1H3 Copy

  
• IUPAC Standard InChIKey: VCZNNAKNUVJVGX-UHFFFAOYSA-N Copy
• CAS Registry Number: 104-85-8
• 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: p-Tolunitrile; p-Cyanotoluene; p-Methylbenzonitrile; p-Toluenenitrile; p-Toluic nitrile; p-Toluonitrile; p-Tolylnitrile; 4-Methylbenzonitrile; 4-Tolunitrile; p-Tolunitril; Nitril kyseliny p-toluylove; 1-Methyl-4-cyanobenzene; 4-Cyanotoluene; 4-Methylcyanobenzene; 4-Toluenkarbonitril; 1-Cyano-4-methylbenzene; NSC 70985
• 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:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Options:
  • Switch to SI 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, Reaction thermochemistry 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:
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

Reduced pressure boiling point

Enthalpy of vaporization

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 by: John E. Bartmess

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

C₈H₆N^- +  =

By formula: C₈H₆N^- + H⁺ = C₈H₇N

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 compiled as indicated in comments:
B - John E. Bartmess
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 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, 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.

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Wright, 1961
Wright, F.J., Influence of temperature on viscosity of nonassociated liquids, J. Chem. Eng. Data, 1961, 6, 454. [all data]

Wright, 1960
Wright, F.J., Latent Heat of Vaporization and Composition, Recl. Trav. Chim. Pays-Bas, 1960, 79, 784-9. [all data]

Perkin, 1896
Perkin, W.H., LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds, J. Chem. Soc., 1896, 69, 1025-1257. [all data]

Stephenson, 1994
Stephenson, R.M., Mutual Solubility of Water and Nitriles, J. Chem. Eng. Data, 1994, 39, 225-7. [all data]

Turner and Merry, 1910
Turner, W.E.S.; Merry, E.W., The Molecular Complexity in the Liq. State of Tervalent Nitrogen Comp., J. Chem. Soc., 1910, 97, 2069. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Kahn, Hehre, et al., 1984
Kahn, S.D.; Hehre, W.J.; Bartmess, J.E.; Caldwell, G., Effect of Metal Complexation on the Gas-phase Acidities of Alkylbenzenes, Organomet., 1984, 3, 11, 1740, https://doi.org/10.1021/om00089a024 . [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]

Johnstone and Mellon, 1973
Johnstone, R.A.W.; Mellon, F.A., Effects of induction and resonance in the calculation of ionization potentials of substituted benzenes by perturbation molecular orbital theory, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 36. [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]

Crable and Kearns, 1962
Crable, G.F.; Kearns, G.L., Effect of substituent groups on the ionization potentials of benzenes, J. Phys. Chem., 1962, 66, 436. [all data]

Palmer, Moyes, et al., 1980
Palmer, M.H.; Moyes, W.; Spiers, M., The electronic structure of substituted benzenes: Ab initio calculations and photoelectron spectra for benzonitrile, the tolunitriles, fluorobenzonitriles, dicyanobenzenes and ethynylbenzene, J. Mol. Struct., 1980, 62, 165. [all data]

Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted benzenes, Bull. Chem. Soc. Jpn., 1974, 47, 2563. [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
  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

• 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.