Benzenamine, N-(phenylmethylene)-
- Formula: C13H11N
- Molecular weight: 181.2331
- IUPAC Standard InChI: InChI=1S/C13H11N/c1-3-7-12(8-4-1)11-14-13-9-5-2-6-10-13/h1-11H
- IUPAC Standard InChIKey: UVEWQKMPXAHFST-UHFFFAOYSA-N
- CAS Registry Number: 538-51-2
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Aniline, N-benzylidene-; Benzalaniline; Benzaldehyde anil; Benzylideneaniline; N-Benzalaniline; N-Benzylidenaniline; N-Benzylideneaniline; M4; N-Phenylbenzenemethanimine; N-Phenylbenzylideneimine; Benzylidene-phenyl-amine; N-(Phenylmethylene)benzenamine; NSC 736
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Gas phase thermochemistry data
Go To: Top, Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 278.7 ± 2.2 | kJ/mol | Ccb | Kirchner, Acree, et al., 1986 |
Condensed phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 185.0 ± 2.0 | kJ/mol | Ccb | Kirchner, Acree, et al., 1986 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -6872.7 ± 1.1 | kJ/mol | Ccb | Kirchner, Acree, et al., 1986 | |
| ΔcH°solid | -6855.5 ± 7.1 | kJ/mol | Ccb | Coates and Sutton, 1948 | Reanalyzed by Cox and Pilcher, 1970, Original value = -6858. ± 7.1 kJ/mol |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.0 | PE | Akaba, Tokumaru, et al., 1980 | LLK |
| 8.25 | PE | Akaba, Tokumaru, et al., 1980 | Vertical value; LLK |
| 8.25 | PE | Kobayashi, Yokota, et al., 1975 | Vertical value; LLK |
| 8.27 ± 0.05 | PE | Goetz, Marschner, et al., 1974 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase 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.
Kirchner, Acree, et al., 1986
Kirchner, J.J.; Acree, W.E., Jr.; Pilcher, G.; Shaofeng, L.,
Enthalpies of combustion of four N-phenylmethylene benzenamine N-oxide derivatives, of N-phenylmethylene benzenamine, and of trans-diphenyldiazene N-oxide: the dissociation enthalpy of the (N-O)bonds,
J. Chem. Thermodyn., 1986, 18, 793-799. [all data]
Coates and Sutton, 1948
Coates, G.E.; Sutton, L.E.,
The heats of formation of the -N=N- and >C=N- bonds,
J. Chem. Soc., 1948, 1187-1196. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Akaba, Tokumaru, et al., 1980
Akaba, R.; Tokumaru, K.; Kobayashi, T.; Utsunomiya, C.,
Electronic structures conformations of N-benzylideneanilines. II. Photoelectron spectral study,
Bull. Chem. Soc. Jpn., 1980, 53, 2002. [all data]
Kobayashi, Yokota, et al., 1975
Kobayashi, T.; Yokota, K.; Nagakura, S.,
Photoelectron spectra of trans-azobenzene and benzalaniline,
J. Electron Spectrosc. Relat. Phenom., 1975, 6, 167. [all data]
Goetz, Marschner, et al., 1974
Goetz, H.; Marschner, F.; Juds, H.,
Zur n-pi Wechselwirkung im Benzalanilin,
Tetrahedron, 1974, 30, 1133. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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