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Benzenamine, N,N,4-trimethyl-

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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

Quantity Value Units Method Reference Comment
Deltafgas68.9 ± 7.4kJ/molCcbRiberio da Silva, Riberio da Silva, et al., 1996 

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

Quantity Value Units Method Reference Comment
Deltafliquid11.7 ± 2.7kJ/molCcbRiberio da Silva, Riberio da Silva, et al., 1996 
Quantity Value Units Method Reference Comment
Deltacliquid-5411.2 ± 2.4kJ/molCcbRiberio da Silva, Riberio da Silva, et al., 1996 

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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil484.2KN/AWeast and Grasselli, 1989BS
Tboil483.15KN/ABroxton, Deady, et al., 1970Uncertainty assigned by TRC = 2. K; TRC
Tboil484.3KN/APerkin, 1896Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Deltavap57.2 ± 6.9kJ/molVRiberio da Silva, Riberio da Silva, et al., 1996ALS
Deltavap57.2kJ/molN/ARiberio da Silva, Riberio da Silva, et al., 1996DRB

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
60.7338.AStephenson and Malanowski, 1987Based on data from 323. - 483. K. See also Stull, 1947.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
323.3 - 482.73.716711364.255-116.036Stull, 1947Coefficents calculated by NIST from author's data.

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:


Reaction 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C9H13N+ + Benzenamine, N,N,4-trimethyl- = (C9H13N+ bullet Benzenamine, N,N,4-trimethyl-)

By formula: C9H13N+ + C9H13N = (C9H13N+ bullet C9H13N)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar70.7kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar(110.)J/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
34.331.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C9H12N- + Hydrogen cation = Benzenamine, N,N,4-trimethyl-

By formula: C9H12N- + H+ = C9H13N

Quantity Value Units Method Reference Comment
Deltar1614. ± 21.kJ/molG+TSCaldwell and Bartmessgas phase; B
Quantity Value Units Method Reference Comment
Deltar1586. ± 21.kJ/molIMRBCaldwell and Bartmessgas phase; B

C10H10Fe+ + Benzenamine, N,N,4-trimethyl- = (C10H10Fe+ bullet Benzenamine, N,N,4-trimethyl-)

By formula: C10H10Fe+ + C9H13N = (C10H10Fe+ bullet C9H13N)

Quantity Value Units Method Reference Comment
Deltar51.0kJ/molPHPMSMeot-Ner (Mautner), 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar86.2J/mol*KPHPMSMeot-Ner (Mautner), 1989gas phase; M

Benzenamine, N,4-dimethyl- = 0.5p-Aminotoluene + 0.5Benzenamine, N,N,4-trimethyl-

By formula: C8H11N = 0.5C7H9N + 0.5C9H13N

Quantity Value Units Method Reference Comment
Deltar-1.kJ/molKinKachurin, Matvienko, et al., 1980liquid phase; ALS

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 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
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

Quantity Value Units Method Reference Comment
IE (evaluated)6.93 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)950.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity918.1kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
6.93EQLias, Jackson, et al., 1985LBLHLM
6.95 ± 0.05EQMautner(Meot-Ner), Nelsen, et al., 1984LBLHLM
6.9 ± 0.1PEEgdell, Green, et al., 1975LLK
6.95PECowling and Johnstone, 1973LLK
7.33CTSFarrell and Newton, 1965RDSH
7.27PEKobayashi and Nagakura, 1974Vertical value; LLK
7.48PEBaker, May, et al., 1968Vertical value; RDSH

De-protonation reactions

C9H12N- + Hydrogen cation = Benzenamine, N,N,4-trimethyl-

By formula: C9H12N- + H+ = C9H13N

Quantity Value Units Method Reference Comment
Deltar1614. ± 21.kJ/molG+TSCaldwell and Bartmessgas phase; B
Quantity Value Units Method Reference Comment
Deltar1586. ± 21.kJ/molIMRBCaldwell and Bartmessgas phase; B

Ion clustering 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: 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C9H13N+ + Benzenamine, N,N,4-trimethyl- = (C9H13N+ bullet Benzenamine, N,N,4-trimethyl-)

By formula: C9H13N+ + C9H13N = (C9H13N+ bullet C9H13N)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar70.7kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Deltar(110.)J/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
34.331.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated

C10H10Fe+ + Benzenamine, N,N,4-trimethyl- = (C10H10Fe+ bullet Benzenamine, N,N,4-trimethyl-)

By formula: C10H10Fe+ + C9H13N = (C10H10Fe+ bullet C9H13N)

Quantity Value Units Method Reference Comment
Deltar51.0kJ/molPHPMSMeot-Ner (Mautner), 1989gas phase
Quantity Value Units Method Reference Comment
Deltar86.2J/mol*KPHPMSMeot-Ner (Mautner), 1989gas phase

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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, 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

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Mass spectrum
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Additional Data

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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- 584
NIST MS number 229670

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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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

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UVVis spectrum
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Additional Data

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Source Bol'shakov, et al., 1969
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. 20179
Instrument SF-4
Boiling point 211

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedCarbowax 20M150.1642.6Ellis and Still, 1979Chromosorb W, AW-DMCS
PackedPEG-20M210.1673.9Still, Evans, et al., 1972Chromosorb G; Column length: 3. m
PackedPEG-20M210.1673.9Still, Evans, et al., 1972Chromosorb G; Column length: 3. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-11160.4Gautzsch and Zinn, 19968. K/min; Tstart: 35. C; Tend: 300. C

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone1162.Zenkevich, 2001Program: not specified
CapillaryMethyl Silicone1163.Zenkevich, 2001Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

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

Riberio da Silva, Riberio da Silva, et al., 1996
Riberio da Silva, M.A.V.; Riberio da Silva, M.D.M.C.; Monteiro, M.F.B.M.; Gomes, M.L.A.C.N.; Chickos, J.S.; Smith, A.P.; Liebman, J.F., Thermochemical studies for determination of the molar enthalpy of formation of aniline derivatives, Struct. Chem., 1996, 7, 367-373. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Broxton, Deady, et al., 1970
Broxton, T.J.; Deady, L.W.; Katritzky, A.R.; Liu, A.; Topsom, R.D., Infrared Intensities as a Quantitative Measure of Intermolecular Inter- actions XII. «pi»-Distortions in teh Ground States of Some p-Alkylbenzenes, J. Am. Chem. Soc., 1970, 92, 6845. [all data]

Perkin, 1896
Perkin, W.H., LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds, J. Chem. Soc., 1896, 69, 1025-1257. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E., , Unpublished results. [all data]

Meot-Ner (Mautner), 1989
Meot-Ner (Mautner), M., Ion DChemistry of Ferrocene. Thermochemistry of Ionization and Protonation and Solvent Clustering. Slow and Entropy - Driven Proton - Transfer Kinetics, J. Am. Chem. Soc., 1989, 111, 8, 2830, https://doi.org/10.1021/ja00190a014 . [all data]

Kachurin, Matvienko, et al., 1980
Kachurin, O.I.; Matvienko, N.M.; Chekhuta, V.G., N-Methylated p-toluidines, Russ. Chem. Rev., 1980, 46, 64-67. [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]

Lias, Jackson, et al., 1985
Lias, S.G.; Jackson, J.-A.A.; Argentar, H.; Liebman, J.F., Substituted N,N-dialkylanilines: Relative ionization energies and proton affinities through determinations of ion-molecule reaction equilibrium constants, J. Org. Chem., 1985, 50, 333. [all data]

Mautner(Meot-Ner), Nelsen, et al., 1984
Mautner(Meot-Ner), M.; Nelsen, S.F.; Willi, M.R.; Frigo, T.B., Special effects of an unusually large neutral to radical cation geometry change. Adiabatic ionization energies and proton affinities of alkylhydrazines, J. Am. Chem. Soc., 1984, 106, 7384. [all data]

Egdell, Green, et al., 1975
Egdell, R.; Green, J.C.; Rao, C.N.R., Photoelectron spectra of substituted benzenes, Chem. Phys. Lett., 1975, 33, 600. [all data]

Cowling and Johnstone, 1973
Cowling, S.A.; Johnstone, R.A.W., Photoelectron spectroscopy: The effects of steric inhibition to resonance in anilines, J. Electron Spectrosc. Relat. Phenom., 1973, 2, 161. [all data]

Farrell and Newton, 1965
Farrell, P.G.; Newton, J., Ionization potentials of aromatic amines, J. Phys. Chem., 1965, 69, 3506. [all data]

Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted benzenes, Bull. Chem. Soc. Jpn., 1974, 47, 2563. [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]

Bol'shakov, et al., 1969
Bol'shakov, G.F., et al., Ultraviolet spectra of heteroorganic compounds, 1969, 167. [all data]

Ellis and Still, 1979
Ellis, T.S.; Still, R.H., Thermal degradation of polymers. XXI. Vacuum pyrolysis of poly(m-N,N-dimethylaminostyrene); the products volatile at pyrolysis temperature, liquid at room temperature, J. Appl. Polym. Sci., 1979, 23, 10, 2837-2854, https://doi.org/10.1002/app.1979.070231002 . [all data]

Still, Evans, et al., 1972
Still, R.H.; Evans, M.B.; Whitehead, A., Thermal Degradation of Polymers. V. Vacuum Pyrolysis of Poly (p-N,N-dimethylaminostyrene) . The Products Volatile at Pyrolysis Temperature, Liquid or Gaseous at Room Temperature, J. Appl. Polym. Sci., 1972, 16, 12, 3207-3221, https://doi.org/10.1002/app.1972.070161213 . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Zenkevich, 2001
Zenkevich, I.G., Comparative Characterization of Conditions for Unambuguous Chromatographic Identification of Organic Compounds, Zh. Anal. Khim., 2001, 56, 9, 915-924. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References