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 Copy

  
• IUPAC Standard InChIKey: UVEWQKMPXAHFST-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Enthalpy of sublimation

Enthalpy of fusion

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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

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

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Meic and Baranovic, 1989
Meic, Z.; Baranovic, G., Vibrational spectra of trans-N-benzylideneaniline and its isotopomers, Pure Appl. Chem., 1989, 61, 2129. [all data]

Verevkin, Morgenthaler, et al., 1997
Verevkin, Sergey P.; Morgenthaler, Jens; Rüchardt, Christoph, Thermochemistry of imines: experimental standard molar enthalpies of formation, The Journal of Chemical Thermodynamics, 1997, 29, 10, 1175-1183, https://doi.org/10.1006/jcht.1997.0242 . [all data]

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., 235. The heats of formation of the ?N?N? and ?C?N? bonds, J. Chem. Soc., 1948, 1187, https://doi.org/10.1039/jr9480001187 . [all data]

Coates and Sutton, 1948, 2
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]

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]

Oszczapowicz, Osek, et al., 1985
Oszczapowicz, J.; Osek, J.; Ciszkowski, K.; Krawczyk, W.; Ostrowski, M., Retention Indices of Dimethylbenzamidines and Benzylideneamines on a Non-Polar Column, J. Chromatogr., 1985, 330, 79-85, https://doi.org/10.1016/S0021-9673(01)81964-6 . [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

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