Benzonitrile, 3-methyl-
- Formula: C8H7N
- Molecular weight: 117.1479
- IUPAC Standard InChI: InChI=1S/C8H7N/c1-7-3-2-4-8(5-7)6-9/h2-5H,1H3
- IUPAC Standard InChIKey: BOHCMQZJWOGWTA-UHFFFAOYSA-N
- CAS Registry Number: 620-22-4
- 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: m-Tolunitrile; m-Cyanotoluene; m-Methylbenzonitrile; m-Toluenenitrile; m-Toluonitrile; 3-Methylbenzonitrile; 3-Tolunitrile; meta-Tolunitrile; m-Tolylnitrile; MTN; Nitril kyseliny m-toluylove; 1-Methyl-3-cyanobenzene; 3-Cyanotoluene; 3-Toluenkarbonitril; m-Tolynitrile; NSC 75453
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Gas phase ion energetics data
Go To: Top, 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 |
|---|---|---|---|
| 9.58 ± 0.05 | EI | Buchs, 1970 | RDSH |
| 9.66 ± 0.05 | EI | Pignataro, Foffani, et al., 1966 | RDSH |
| 9.34 | PE | Palmer, Moyes, et al., 1980 | Vertical value; LLK |
| 9.40 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
De-protonation reactions
C8H6N- + =
By formula: C8H6N- + H+ = C8H7N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 369.2 ± 2.1 | kcal/mol | G+TS | Caldwell and Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 362.1 ± 2.0 | kcal/mol | IMRE | Caldwell and Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, 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.
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]
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]
Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E.,
, Unpublished results. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
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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