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:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
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Gas phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

IR Spectrum

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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: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

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.

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]

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]

Coates and Sutton, 1948, 2
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]

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]

Haselbach and Heilbronner, 1968
Haselbach, E.; Heilbronner, E., Helv. Chim. Acta, 1968, 51, 16. [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
  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
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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