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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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
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 490.8 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 491.3 | K | N/A | Wright, 1961 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tboil | 491.3 | K | N/A | Wright, 1960 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 490.75 | K | N/A | Perkin, 1896 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 299.7 | K | N/A | Stephenson, 1994 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 301.55 | K | N/A | Turner and Merry, 1910 | Uncertainty assigned by TRC = 0.5 K; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
377.7 | 0.026 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.5 | 330. | A | Stephenson and Malanowski, 1987 | Based on data from 315. to 491. K. See also Stull, 1947.; AC |
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- + =
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
Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
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
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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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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 |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | OV-101 | 100. | 1072. | West and Hall, 1975 | Gas Chrom Q; Column length: 2. m |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1928. | Shimoda, Shigematsu, et al., 1995 | 60. m/0.25 mm/0.25 μm, 2. K/min; Tstart: 50. C; Tend: 230. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 1050. | Ibrahim and Suffet, 1988 | N2; Column length: 60. m; Column diameter: 0.32 mm; Program: 50C(8min) => 3C/min => 150C => 35C/min => 275C (10min) |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 177.8 | Wang, Hou, et al., 2007 | 30. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
Capillary | HP-5 | 178.1 | Shao, Wang, et al., 2006 | 30. m/0.3 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]
West and Hall, 1975
West, S.D.; Hall, R.C.,
Substituent contributions to the Kováts retention indices of benzene derivatives,
J. Chromatogr. Sci., 1975, 13, 5-11. [all data]
Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y.,
Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion,
J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037
. [all data]
Ibrahim and Suffet, 1988
Ibrahim, E.A.; Suffet, I.H.,
Freon FC-113, an Alternative to Methylene Chloride for Liquid-Liquid Extraction of Trace Organics from Chlorinated Drinking Water,
J. Chromatogr., 1988, 454, 217-232, https://doi.org/10.1016/S0021-9673(00)88615-X
. [all data]
Wang, Hou, et al., 2007
Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S.,
Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods,
Chem. Anal., 2007, 52, 141-156. [all data]
Shao, Wang, et al., 2006
Shao, X.; Wang, G.; Sun, Y.; Zhang, R.; Xie, K.; Liu, H.,
Determination and Characterization of the Pyrolysis Products of Isoprocarb by GC-MS,
J. Chromatogr. Sci., 2006, 44, 3, 141-147, https://doi.org/10.1093/chromsci/44.3.141
. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
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