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Benzyl nitrile

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Phase change data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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

Quantity Value Units Method Reference Comment
Tboil506. ± 4.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus250.71KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.3 K; TRC
Tfus251.15KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Deltavap14.5 ± 0.2kcal/molGSVerevkin, 2000Based on data from 283. - 328. K.; AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
14.4 ± 0.2306.GSVerevkin, 2000Based on data from 283. - 328. K.; AC
13.1348.AStephenson and Malanowski, 1987Based on data from 333. - 507. K. See also Stull, 1947.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
333. - 506.74.887352288.897-38.465Stull, 1947Coefficents calculated by NIST from author's data.

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 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- + Hydrogen cation = Benzyl nitrile

By formula: C8H6N- + H+ = C8H7N

Quantity Value Units Method Reference Comment
Deltar350.7 ± 2.3kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar351.5 ± 3.2kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar344.1 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar344.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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)

Quantity Value Units Method Reference Comment
IE (evaluated)9.39 ± 0.07eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)192.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity185.2kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.32 ± 0.05EISelim, Rabbih, et al., 1987LBLHLM
9.34EIVan Der Greef, Molenaar-Langeveld, et al., 1979LLK
9.50 ± 0.04EIBuchs, 1970RDSH
9.40 ± 0.05EIPignataro, Foffani, et al., 1966RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H3+17.31 ± 0.10HCN+H+C2H2EISelim, Rabbih, et al., 1989LL
C5H3+18.36 ± 0.12CN+H2+C2H2EISelim, Rabbih, et al., 1989LL
C7H6+12.23 ± 0.05HCNEISelim, Rabbih, et al., 1987, 2LBLHLM
C7H6+12.19HCNEIVan Der Greef, Molenaar-Langeveld, et al., 1979LLK
C7H7+12.58 ± 0.09CNEISelim, Rabbih, et al., 1987, 3LBLHLM
C8H6N+12.46 ± 0.06HEISelim, Rabbih, et al., 1987LBLHLM

De-protonation reactions

C8H6N- + Hydrogen cation = Benzyl nitrile

By formula: C8H6N- + H+ = C8H7N

Quantity Value Units Method Reference Comment
Deltar350.7 ± 2.3kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar351.5 ± 3.2kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar344.1 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar344.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

IR Spectrum

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

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


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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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
NIST MS number 2007

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References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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]

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]

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]


Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References