Aniline, N-methyl-

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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
Δfgas20.1 ± 1.5kcal/molCmGuthrie, Barker, et al., 1993 
Δfgas20.4kcal/molCcbVriens and Hill, 1952 

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid8.0 ± 1.8kcal/molCmGuthrie, Barker, et al., 1993ALS
Δfliquid7.7kcal/molCcbVriens and Hill, 1952ALS
Quantity Value Units Method Reference Comment
Δcliquid-973.5kcal/molCcbVriens and Hill, 1952ALS
Δcliquid-974.4kcal/molCcbGarner and Abernethy, 1921ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
49.50298.Lesbats and Lichanot, 1987T = 220 to 325 K.; DH
55.00290.Kurnakov and Voskresenskaya, 1936DH

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, Chris Muzny director
DH - Eugene S. Domalski and Elizabeth D. Hearing
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
Tboil468. ± 3.KAVGN/AAverage of 13 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus216.KN/ALesbats and Lichanot, 1987DH
Quantity Value Units Method Reference Comment
Pc51.3000atmN/AHerz and Neukirch, 1923Uncertainty assigned by TRC = 0.6999 atm; TRC
Quantity Value Units Method Reference Comment
Δvap12.1 ± 1.0kcal/molEGuthrie, Barker, et al., 1993ALS
Δvap12.1kcal/molN/AGuthrie, Barker, et al., 1993DRB
Δvap12.7kcal/molVVriens and Hill, 1952ALS
Δvap12.8kcal/molN/AVriens and Hill, 1952DRB

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
12.8324.AStephenson and Malanowski, 1987Based on data from 309. to 469. K.; AC
10.84466.6VMathews and Fehlandt, 1931ALS

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
323. to 472.764.988382226.576-22.456Nelson and Wales, 1925Coefficents 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

C7H9N+ + Aniline, N-methyl- = (C7H9N+ • Aniline, N-methyl-)

By formula: C7H9N+ + C7H9N = (C7H9N+ • C7H9N)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr16.4kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr23.3cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C7H8N- + Hydrogen cation = Aniline, N-methyl-

By formula: C7H8N- + H+ = C7H9N

Quantity Value Units Method Reference Comment
Δr364.8 ± 2.1kcal/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr357.5 ± 2.0kcal/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale; B

Aniline, N-methyl- = 0.5Benzenamine, N,N-dimethyl- + 0.5Aniline

By formula: C7H9N = 0.5C8H11N + 0.5C6H7N

Quantity Value Units Method Reference Comment
Δr-0.8kcal/molEqkMatvienko, Kachurin, et al., 1982liquid phase; Methansulfonic acid; ALS
Δr-0.9kcal/molKinKachurin, Matvienko, et al., 1979liquid 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
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C7H9N+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)7.32 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)219.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity212.7kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.38 ± 0.05EQMautner(Meot-Ner), Nelsen, et al., 1984LBLHLM
7.3PEKlasinc, Kovac, et al., 1983LBLHLM
7.35 ± 0.02PEMaier and Turner, 1973LLK
7.32PECowling and Johnstone, 1973LLK
7.30 ± 0.05PIAkopyan and Vilesov, 1964RDSH
7.34 ± 0.02PIVilesov and Terenin, 1957RDSH
7.53PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
7.73PEBaker, May, et al., 1968Vertical value; RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H6+10.98 ± 0.09?EISelim, Rabbih, et al., 1992LL
C7H8N+11.0 ± 0.1HPIAkopyan and Vilesov, 1964RDSH

De-protonation reactions

C7H8N- + Hydrogen cation = Aniline, N-methyl-

By formula: C7H8N- + H+ = C7H9N

Quantity Value Units Method Reference Comment
Δr364.8 ± 2.1kcal/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr357.5 ± 2.0kcal/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale; B

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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: 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

C7H9N+ + Aniline, N-methyl- = (C7H9N+ • Aniline, N-methyl-)

By formula: C7H9N+ + C7H9N = (C7H9N+ • C7H9N)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr16.4kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Δr23.3cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated

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, Notes

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

Guthrie, Barker, et al., 1993
Guthrie, J.P.; Barker, J.; Cullimore, P.A.; Lu, J.; Pike, D.C., The tetrahedral intermediate from the hydration of N-methylformanilide, Can. J. Chem., 1993, 71, 2111-2122. [all data]

Vriens and Hill, 1952
Vriens, G.N.; Hill, A.G., Equilibria of several reactions of aromatic amines, Ind. Eng. Chem., 1952, 44, 2732-27. [all data]

Garner and Abernethy, 1921
Garner, W.E.; Abernethy, C.L., Heats of combustion and formation of nitro-compounds. Part I. - Benzene, toluene, phenol and methylaniline series, Proc. Roy. Soc. London A, 1921, 213-235. [all data]

Lesbats and Lichanot, 1987
Lesbats, C.; Lichanot, A., Capacites calorifiques de durcisseurs amines et resines epoxydes, Thermochim. Acta, 1987, 109, 317-329. [all data]

Kurnakov and Voskresenskaya, 1936
Kurnakov, N.S.; Voskresenskaya, N.K., Calorimetry of liquid binary systems, Izv. Akad. Nauk SSSR, Otdel. Mat. i Estestv. Nauk. Ser. Khim, 1936, 1936, 439-461. [all data]

Herz and Neukirch, 1923
Herz, W.; Neukirch, E., On Knowldge of the Critical State, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1923, 104, 433-50. [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]

Mathews and Fehlandt, 1931
Mathews, J.H.; Fehlandt, P.R., The heats of vaporization of some organic compounds, J. Am. Chem. Soc., 1931, 53, 3212-32. [all data]

Nelson and Wales, 1925
Nelson, O.A.; Wales, H., Vapor Pressures and Boiling Points of Mono- and Dimthylanilines and Mono- and Diethylanilines, J. Am. Chem. Soc., 1925, 47, 3, 867-872, https://doi.org/10.1021/ja01680a040 . [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]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Matvienko, Kachurin, et al., 1982
Matvienko, N.M.; Kachurin, O.I.; Chekhuta, V.G., Kinetics and equilibrium of the transalkylation reaction of N-methylarylamines, Russ. Chem. Rev., 1982, 48, 42-45. [all data]

Kachurin, Matvienko, et al., 1979
Kachurin, O.I.; Matvienko, N.M.; Chekhuta, V.G., Disproportionation of N-methylaniline, Russ. Chem. Rev., 1979, 45, 43-47. [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]

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]

Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H., Photoelectron spectra of acenes. Electronic structure and substituent effects, Pure Appl. Chem., 1983, 55, 289. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [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]

Akopyan and Vilesov, 1964
Akopyan, M.E.; Vilesov, F.I., Excited states of positive ions and dissociative photoionization of aromatic amines, Dokl. Akad. Nauk SSSR, 1964, 158, 1386, In original 965. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [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]

Selim, Rabbih, et al., 1992
Selim, E.T.M.; Rabbih, M.A.; Fahmey, M.A.; Hawash, M.F., Electron impact study of [C6H6]+ fragment ions produced from isomeric C7H9N precursors using the deconvoluted first differential technique and kinetic release measurements, Int. J. Mass Spectrom. Ion Processes, 1992, 113, 133. [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, References