Benzonitrile, 4-methyl-
- Formula: C8H7N
- Molecular weight: 117.1479
- IUPAC Standard InChIKey: VCZNNAKNUVJVGX-UHFFFAOYSA-N
- 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
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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
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Individual Reactions
C8H6N- + =
By formula: C8H6N- + H+ = C8H7N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 360.5 ± 2.4 | kcal/mol | G+TS | Kahn, Hehre, et al., 1984 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 353.3 ± 2.3 | kcal/mol | IMRE | Kahn, Hehre, et al., 1984 | gas phase; value altered from reference due to change in acidity scale |
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 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
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.32 | EI | Van Der Greef, Molenaar-Langeveld, et al., 1979 | LLK |
9.31 | EI | Johnstone and Mellon, 1973 | LLK |
9.56 ± 0.05 | EI | Buchs, 1970 | RDSH |
9.76 | EI | Crable and Kearns, 1962 | RDSH |
9.38 | PE | Palmer, Moyes, et al., 1980 | Vertical value; LLK |
9.33 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H6+ | 12.22 | HCN | EI | Van Der Greef, Molenaar-Langeveld, et al., 1979 | LLK |
De-protonation reactions
C8H6N- + =
By formula: C8H6N- + H+ = C8H7N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 360.5 ± 2.4 | kcal/mol | G+TS | Kahn, Hehre, et al., 1984 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 353.3 ± 2.3 | kcal/mol | IMRE | Kahn, Hehre, et al., 1984 | gas phase; value altered from reference due to change in acidity scale; B |
IR Spectrum
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
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. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 881 |
NIST MS number | 228796 |
UV/Visible spectrum
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.
Spectrum
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Additional Data
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Source | Bol'shakov, et al., 1969 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 20185 |
Instrument | SF-4 |
Melting point | 29.5 |
Boiling point | 217 |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Bol'shakov, et al., 1969
Bol'shakov, G.F., et al.,
Ultraviolet spectra of heteroorganic compounds, 1969, 175. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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