Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

NOTICE: Due to scheduled maintenance at our Gaithersburg campus, this site will not be available from 5:00 pm EDT (21:00 UTC) on Friday October 25 until 5:00 pm (21:00 UTC) on Sunday October 27. We apologize for any inconvenience this outage may cause.

Benzenamine, N-(phenylmethylene)-

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
Deltafgas66.61 ± 0.53kcal/molCcbKirchner, Acree, et al., 1986 

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
Deltafsolid44.22 ± 0.48kcal/molCcbKirchner, Acree, et al., 1986 
Quantity Value Units Method Reference Comment
Deltacsolid-1642.6 ± 0.26kcal/molCcbKirchner, Acree, et al., 1986 
Deltacsolid-1638.5 ± 1.7kcal/molCcbCoates and Sutton, 1948Reanalyzed by Cox and Pilcher, 1970, Original value = -1639. ± 1.7 kcal/mol

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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:
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.

Quantity Value Units Method Reference Comment
Tfus324.15KN/AMeic and Baranovic, 1989Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Deltasub23.4 ± 0.29kcal/molTVerevkin, Morgenthaler, et al., 1997AC
Deltasub22.4 ± 0.2kcal/molCKirchner, Acree, et al., 1986ALS
Deltasub22.4kcal/molN/AKirchner, Acree, et al., 1986DRB
Deltasub22.4 ± 0.2kcal/molCKirchner, Acree, et al., 1986AC

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
23.3 ± 0.29309.TVerevkin, Morgenthaler, et al., 1997Based on data from 294. - 326. K.; AC
20.4 ± 0.50293.ESTCoates and Sutton, 1948, 2AC
20.5 ± 0.5293.VCoates and Sutton, 1948ALS

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
4.880329.7Verevkin, Morgenthaler, et al., 1997AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
8.0PEAkaba, Tokumaru, et al., 1980LLK
8.25PEAkaba, Tokumaru, et al., 1980Vertical value; LLK
8.25PEKobayashi, Yokota, et al., 1975Vertical value; LLK
8.27 ± 0.05PEGoetz, Marschner, et al., 1974Vertical value; LLK

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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: Coblentz Society, Inc.

Condensed Phase Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

IR spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

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

View scan of original (hardcopy) spectrum.

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Owner COBLENTZ SOCIETY
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin DOW CHEMICAL COMPANY
Source reference COBLENTZ NO. 6257
Date 1965/07/07
Name(s) N-phenyl-N-[(E)-phenylmethylidene]amine
N-[(E)-phenylmethylidene]aniline
State SOLUTION (10% IN CCl4 FOR 3800-1340, 10% IN CS2 FOR 1340-400 CM-1) VS. SOLVENT
Instrument DOW KBr FOREPRISM-GRATING
Instrument parameters BLAZED AT 3.5, 12.0, 20.0 MICRONS AND CHANGED AT 5.0, 7.5, 14.9 MICRONS
Path length 0.011 CM, 0.011 CM
Resolution 2
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS)

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-5563
NIST MS number 229011

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

UVVis spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Source Haselbach and Heilbronner, 1968
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 15188
Instrument unknown
Melting point 52
Boiling point 128-132

References

Go To: Top, 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, 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]

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]


Notes

Go To: Top, 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, References