Benzonitrile
- Formula: C7H5N
- Molecular weight: 103.1213
- IUPAC Standard InChIKey: JFDZBHWFFUWGJE-UHFFFAOYSA-N
- CAS Registry Number: 100-47-0
- 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: Benzene, cyano-; Benzoic acid nitrile; Cyanobenzene; Phenyl cyanide; Benzenenitrile; Fenylkyanid; UN 2224
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Gas phase thermochemistry 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 219.0 | kJ/mol | N/A | Lebedev, Bykova, et al., 1985 | Value computed using ΔfHliquid° value of 163.2±1.5 kj/mol from Lebedev, Bykova, et al., 1985 and ΔvapH° value of 55.8 kj/mol from Evans and Skinner, 1959.; DRB |
ΔfH°gas | 219. | kJ/mol | Ccb | Evans and Skinner, 1959 | ALS |
Reaction thermochemistry data
Go To: Top, Gas phase 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
By formula: Br- + C7H5N = (Br- • C7H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.5 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff measured at 423 K, ΔSaff taken as that of PhNO2..Br-; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 84. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 26. ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff measured at 423 K, ΔSaff taken as that of PhNO2..Br-; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
26. | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
By formula: Cl- + C7H5N = (Cl- • C7H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.9 | kJ/mol | PHPMS | Paul and Kebarle, 1991 | gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 84. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
41.8 | 300. | PHPMS | Paul and Kebarle, 1991 | gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M |
C7H4N- + =
By formula: C7H4N- + H+ = C7H5N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1603. ± 10. | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1567. ± 8.4 | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
By formula: C6H7N+ + C7H5N = (C6H7N+ • C7H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 81.2 | kJ/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 88. | J/mol*K | N/A | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
51.5 | 338. | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
By formula: C11H10+ + C7H5N = (C11H10+ • C7H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.5 | kJ/mol | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
29. | 301. | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; Entropy change calculated or estimated; M |
By formula: NO- + C7H5N = (NO- • C7H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 172. | kJ/mol | ICR | Reents and Freiser, 1981 | gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M |
By formula: CH6N+ + C7H5N = (CH6N+ • C7H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 123. | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 131. | J/mol*K | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; M |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry 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 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
LL - Sharon G. Lias and Joel F. Liebman
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
View reactions leading to C7H5N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.73 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 811.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 780.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.26 ± 0.10 | ECD | Zlatkis, Lee, et al., 1983 | B |
0.256 ± 0.017 | ECD | Wentworth, Kao, et al., 1975 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.7316 ± 0.0002 | TE | Araki and Sato, 1996 | LL |
9.6 | PE | Klasinc, Kovac, et al., 1983 | LBLHLM |
10.13 ± 0.03 | EI | Baldwin, 1979 | LLK |
9.69 | PE | Behan, Johnstone, et al., 1976 | LLK |
9.62 | PE | Rabalais and Colton, 1973 | LLK |
9.7 | EI | McLafferty, Bente, et al., 1973 | LLK |
9.77 | EI | Cooks, Bertrand, et al., 1973 | LLK |
9.71 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.79 | PE | Klasinc, Kovac, et al., 1983 | Vertical value; LBLHLM |
9.8 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
9.71 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
9.71 | PE | Palmer, Moyes, et al., 1980 | Vertical value; LLK |
9.70 | PE | Neijzen and DeLange, 1978 | Vertical value; LLK |
9.72 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
9.70 | PE | Griebel, Hohlneicher, et al., 1974 | Vertical value; LLK |
10.02 | PE | Baker, May, et al., 1968 | Vertical value; RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H4+ | 13.8 ± 0.1 | HCN | EI | Burgers and Holmes, 1982 | LBLHLM |
C6H4+ | 12.54 ± 0.03 | HCN | EI | Maccoll and Mathur, 1981 | LLK |
C6H4+ | 12.64 ± 0.03 | HCN | PIPECO | Rosenstock, Stockbauer, et al., 1980 | LLK |
C6H4+ | 13.38 ± 0.03 | HCN | EI | Baldwin, 1979 | LLK |
C6H4+ | 13.80 ± 0.06 | HCN | EI | Bentley, Johnstone, et al., 1973 | LLK |
C6H4+ | 13.9 ± 0.1 | HCN | EI | Gross, 1972 | LLK |
C6H4+ | 14.60 | HCN | EI | Howe and Williams, 1969 | RDSH |
C6H5+ | 13.52 ± 0.05 | CN | EI | Burgers and Holmes, 1984 | LBLHLM |
C6H5+ | 13.8 | CN | EI | Burgers and Holmes, 1984 | LBLHLM |
De-protonation reactions
C7H4N- + =
By formula: C7H4N- + H+ = C7H5N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1603. ± 10. | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1567. ± 8.4 | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
References
Go To: Top, Gas phase thermochemistry 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.
Lebedev, Bykova, et al., 1985
Lebedev, B.V.; Bykova, T.A.; Kiparisova, E.G.; Chernomordik, Yu.A.; Kurapov, A.S.; Sergeev, V.A.,
Thermodynamic study of benzonitrile, the process of its cocyclotrimerization with phenylacetylene, and the 2,4,6-triphenylpyridine that is formed, in the interval 0-330°K,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985, 274-279. [all data]
Evans and Skinner, 1959
Evans, F.W.; Skinner, H.A.,
The heats of combustion of organic compounds of nitrogen Part 2.-n-Propyl, isopropyl and phenyl cyandies,
Trans. Faraday Soc., 1959, 55, 255-259. [all data]
Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P.,
Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-,
J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014
. [all data]
Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A.,
Carbon Acidities of Aromatic Compounds,
J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003
. [all data]
Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B.,
Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine,
J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z
. [all data]
Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S.,
Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems,
J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026
. [all data]
El-Shall and Meot-Ner (Mautner), 1987
El-Shall, M.S.; Meot-Ner (Mautner), M.,
Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors,
J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017
. [all data]
Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S.,
Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes,
J. Am. Chem. Soc., 1981, 103, 2791. [all data]
Farid and McMahon, 1978
Farid, R.; McMahon, T.B.,
Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy,
Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0
. [all data]
Speller and Meot-Ner (Mautner), 1985
Speller, C.V.; Meot-Ner (Mautner), M.,
The Ionic Hydrogen Bond and Ion Solvation. 3. Bonds Involving Cyanides. Correlations with Proton Affinites,
J. Phys. Chem., 1985, 81, 24, 5217, https://doi.org/10.1021/j100270a020
. [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]
Zlatkis, Lee, et al., 1983
Zlatkis, A.; Lee, C.K.; Wentworth, W.E.; Chen, E.C.M.,
Constant current linearization for determination of electron capture mechanisms,
Anal. Chem., 1983, 55, 1596. [all data]
Wentworth, Kao, et al., 1975
Wentworth, W.E.; Kao, L.W.; Becker, R.S.,
Electron affinities of substituted aromatic compounds,
J. Phys. Chem., 1975, 79, 1161. [all data]
Araki and Sato, 1996
Araki, M.; Sato, S.-i.,
Two-color zero kinetic energy photoelectron spectra of benzonitrile and its van der Waals complexes with argon. Adiabatic ionization potentials and cation vibrational frequencies,
J. Phys. Chem., 1996, 100, 10542. [all data]
Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H.,
Photoelectron spectra of acenes. Electronic structure and substituent effects,
Pure Appl. Chem., 1983, 55, 289. [all data]
Baldwin, 1979
Baldwin, M.A.,
Appearance energies and the kinetic shift. Loss of HCN from the benzonitrile molecular ion,
Org. Mass Spectrom., 1979, 14, 601. [all data]
Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W.,
An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes,
Org. Mass Spectrom., 1976, 11, 207. [all data]
Rabalais and Colton, 1973
Rabalais, J.W.; Colton, R.J.,
Electronic interaction between the phenyl group and its unsaturated substituents,
J. Electron Spectrosc. Relat. Phenom., 1973, 1, 83. [all data]
McLafferty, Bente, et al., 1973
McLafferty, F.W.; Bente, P.F., III; Kornfeld, R.; Tsai, S.-C.; Howe, I.,
Collisional activation spectra of organic ions,
J. Am. Chem. Soc., 1973, 95, 2120. [all data]
Cooks, Bertrand, et al., 1973
Cooks, R.G.; Bertrand, M.; Beynon, J.H.; Rennekamp, M.E.; Setser, D.W.,
Energy partitioning data as an ion structure probe. Substituted anisoles,
J. Am. Chem. Soc., 1973, 95, 1732. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [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]
Neijzen and DeLange, 1978
Neijzen, B.J.M.; DeLange, C.A.,
Photoelectron spectroscopy of mono-dicyanobenzenes their perfluoro derivatives,
J. Electron Spectrosc. Relat. Phenom., 1978, 14, 187. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Griebel, Hohlneicher, et al., 1974
Griebel, R.; Hohlneicher, G.; Dorr, F.,
A photoelectron spectroscopic study of benzonitrile, ethynylbenzene and some of its substituted derivatives,
J. Electron Spectrosc. Relat. Phenom., 1974, 4, 185. [all data]
Baker, May, et al., 1968
Baker, A.D.; May, D.P.; Turner, D.W.,
Molecular photoelectron spectroscopy. Part VII. The vertical ionisation potentials of benzene and some of its monosubstituted and 1,4-disubstituted derivatives,
J. Chem. Soc. B, 1968, 22. [all data]
Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L.,
Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks,
Org. Mass Spectrom., 1982, 17, 123. [all data]
Maccoll and Mathur, 1981
Maccoll, A.; Mathur, D.,
On the heat of formation of [C6H4],
Org. Mass Spectrom., 1981, 16, 261. [all data]
Rosenstock, Stockbauer, et al., 1980
Rosenstock, H.M.; Stockbauer, R.; Parr, A.C.,
Photoelectron-photoion coincidence study of benzonitrile,
J. Chim. Phys., 1980, 77, 745. [all data]
Bentley, Johnstone, et al., 1973
Bentley, T.W.; Johnstone, R.A.W.; McMaster, B.N.,
Appearance potentials of metastable and normal ions and the kinetic shift,
J. Chem. Soc., Chem. Commun., 1973, 510. [all data]
Gross, 1972
Gross, M.L.,
Ion cyclotron resonance spectrometry. A means of evaluating 'kinetic shifts',
Org. Mass Spectrom., 1972, 6, 827. [all data]
Howe and Williams, 1969
Howe, I.; Williams, D.H.,
Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes,
J. Am. Chem. Soc., 1969, 91, 7137. [all data]
Burgers and Holmes, 1984
Burgers, P.C.; Holmes, J.L.,
Fragmentation rate constants and appearance energies for reactions having a large kinetic shift and the energy partitioning in their metastable decomposition,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 15. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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