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p-Aminotoluene

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Deltafgas9.99kcal/molCcbDraeger, 1984ALS
Deltafgas14.9kcal/molN/APushin, 1954Value computed using «DELTA»fHliquid° value of 19 kj/mol from Pushin, 1954 and «DELTA»vapH° value of 43.18 kj/mol from missing citation.; DRB

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
Deltafliquid4.5kcal/molCcbPushin, 1954Author's hf298_condensed=1.8 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-970.2kcal/molCcbPushin, 1954Author's hf298_condensed=1.8 kcal/mol; ALS
Deltacliquid-970.69kcal/molCcbSwarts, 1909ALS

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
39.48298.15Meva'a and Lichanot, 1990T = 273 to 368 K. Cp(c) = 147.505 + 0.604T + 3.525x10-3T2 + 2.351x10-5T3 J/mol*K (-100 to 30 C). Cp(liq) = 212.982 + 0.182T J/mol*K (50 to 95 C).; DH
29.71293.Campbell and Campbell, 1940DH

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
AC - William E. Acree, Jr., James S. Chickos
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
Tboil474. ± 1.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus317. ± 2.KAVGN/AAverage of 25 out of 26 values; Individual data points
Quantity Value Units Method Reference Comment
Tc667.15KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc23.5000atmN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2.0000 atm; TRC
Quantity Value Units Method Reference Comment
Deltavap13.8 ± 0.07kcal/molGSEmel'yanenk and Verevkin, 2005Based on data from 319. - 345. K.; AC
Deltavap10.32kcal/molCGlaser and Ruland, 1957ALS
Deltavap14.8kcal/molN/AGlaser and Rüland, 1957Based on data from 474. - 641. K. See also Emel'yanenk and Verevkin, 2005.; AC
Deltavap13.4kcal/molEBBerliner and May, 1927Based on data from 313. - 473. K. See also Emel'yanenk and Verevkin, 2005.; AC
Quantity Value Units Method Reference Comment
Deltasub18.2 ± 0.07kcal/molGSEmel'yanenk and Verevkin, 2005Based on data from 284. - 313. K.; AC
Deltasub18.8 ± 0.1kcal/molN/AChao, Gadalla, et al., 1990AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
12.2408.AStephenson and Malanowski, 1987Based on data from 393. - 474. K.; AC
13.1330.N/AStull, 1947Based on data from 315. - 473. K.; AC

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
315. - 473.64.713131961.716-57.00Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
4.1348316.55Meva'a and Lichanot, 1990DH
4.109317.Censký, Lipovská, et al., 2001AC
4.276316.5Acree, 1991AC
4.13316.6Meva'a and Lichanot, 1990AC
4.52316.9Rastogi, Nigam, et al., 1963AC
4.130315.6Eykman, 1889AC
4.1300315.6Eykman, 1889, 2DH

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
13.316.55Meva'a and Lichanot, 1990DH

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:
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

C7H8N- + Hydrogen cation = p-Aminotoluene

By formula: C7H8N- + H+ = C7H9N

Quantity Value Units Method Reference Comment
Deltar367.3 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar360.1 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

p-Aminotoluene + Benzoyl iodide = Hydrogen iodide + Benzamide, N-(4-methylphenyl)-

By formula: C7H9N + C7H5IO = HI + C14H13NO

Quantity Value Units Method Reference Comment
Deltar-40.2 ± 0.4kcal/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene; ALS

p-Aminotoluene + Benzoyl bromide = Hydrogen bromide + Benzamide, N-(4-methylphenyl)-

By formula: C7H9N + C7H5BrO = HBr + C14H13NO

Quantity Value Units Method Reference Comment
Deltar-40.7 ± 0.2kcal/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene; ALS

p-Aminotoluene + Benzoyl chloride = Benzamide, N-(4-methylphenyl)- + Hydrogen chloride

By formula: C7H9N + C7H5ClO = C14H13NO + HCl

Quantity Value Units Method Reference Comment
Deltar-39.3 ± 0.3kcal/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene; ALS

C15H16N2O = p-Aminotoluene + Benzene, 1-isocyanato-4-methyl-

By formula: C15H16N2O = C7H9N + C8H7NO

Quantity Value Units Method Reference Comment
Deltar34.9 ± 0.2kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

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-0.3kcal/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

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C7H9N+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)214.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity206.7kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.37PECowling and Johnstone, 1973LLK
7.24 ± 0.02PIPotapov and Iskakov, 1971LLK
7.6 ± 0.1CTSFarrell and Newton, 1966RDSH
7.6 ± 0.1EIEland, Shepherd, et al., 1966RDSH
7.58CTSKinoshita, 1962RDSH
7.65CTSBriegleb and Czekalla, 1959RDSH
7.81PEPalmer, Moyes, et al., 1979Vertical value; LLK
7.85 ± 0.05PESzepes, Distefano, et al., 1974Vertical value; LLK
7.62PEKobayashi and Nagakura, 1972Vertical value; LLK
7.78PEBaker, May, et al., 1968Vertical value; RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H8N+11.0 ± 0.1HPIPotapov and Iskakov, 1971LLK
C7H8N+10.80HEIHowe and Williams, 1969RDSH

De-protonation reactions

C7H8N- + Hydrogen cation = p-Aminotoluene

By formula: C7H8N- + H+ = C7H9N

Quantity Value Units Method Reference Comment
Deltar367.3 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar360.1 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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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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-8703
NIST MS number 228036

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, 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

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UVVis spectrum
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Additional Data

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Source Lang (editor), 1961
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. 19750
Instrument Beckman Model DU
Melting point 44-45

References

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

Draeger, 1984
Draeger, J.A., Chemical-thermodynamic properties of molecules that undergo inversion. II. The methylanilines, J. Chem. Thermodyn., 1984, 16, 1067-1073. [all data]

Pushin, 1954
Pushin, N.A., Heats of combustion and heats of formation of isomeric organic compounds, Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]

Swarts, 1909
Swarts, M.F., Sur la chaleur de formation de l'aniline et de quelquesuns de ses derives, Recl. Trav. Chim. Pays-Bas, 1909, 28, 155-165. [all data]

Meva'a and Lichanot, 1990
Meva'a, L.M.; Lichanot, A., Proprietes thermodynamiques en phase condensee des ortho, meta et para fluorotoluene, cresol et toluidine, Thermochim. Acta, 1990, 158, 335-345. [all data]

Campbell and Campbell, 1940
Campbell, A.N.; Campbell, A.J.R., The heats of solution, heats of formation, specific heats and equilibrium diagrams of certain molecular compounds. J. Am. Chem. Soc., 1940, 62, 291-297. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Emel'yanenk and Verevkin, 2005
Emel'yanenk, Vladimir N.; Verevkin, Sergey P., Enthalpies of Formation and Substituent Effects of o rtho -, m eta- , and p ara -Aminotoluenes from Thermochemical Measurements and from Ab Initio Calculations, J. Phys. Chem. A, 2005, 109, 17, 3960-3966, https://doi.org/10.1021/jp045450i . [all data]

Glaser and Rüland, 1957
Glaser, Fritz; Rüland, Heinz, Untersuchungen über Dampfdruckkurven und kritische Daten einiger technisch wichtiger organischer Substanzen, Chemie Ing. Techn., 1957, 29, 12, 772-775, https://doi.org/10.1002/cite.330291204 . [all data]

Berliner and May, 1927
Berliner, J.F.T.; May, Orville E., STUDIES IN VAPOR PRESSURE. III. THE TOLUIDINES, J. Am. Chem. Soc., 1927, 49, 4, 1007-1011, https://doi.org/10.1021/ja01403a017 . [all data]

Chao, Gadalla, et al., 1990
Chao, J.; Gadalla, N.A.M.; Gammon, B.E.; Marsh, K.N.; Rodgers, A.S.; Somayajulu, G.R.; Wilhoit, R.C., Thermodynamic and Thermophysical Properties of Organic Nitrogen Compounds. Part I. Methanamine, Ethanamine, 1- and 2-Propanamine, Benzenamine, 2-, 3-, and 4-Methylbenzenamine, J. Phys. Chem. Ref. Data, 1990, 19, 6, 1547, https://doi.org/10.1063/1.555849 . [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]

Censký, Lipovská, et al., 2001
Censký, M.; Lipovská, M.; Schmidt, H.-G.; Ruzicka, V.; Wolf, G., Journal of Thermal Analysis and Calorimetry, 2001, 63, 3, 879-899, https://doi.org/10.1023/A:1010125128496 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Rastogi, Nigam, et al., 1963
Rastogi, R.P.; Nigam, R.K.; Sharma, R.N.; Girdhar, H.L., Entropy of Fusion of Molecular Complexes, J. Chem. Phys., 1963, 39, 11, 3042, https://doi.org/10.1063/1.1734140 . [all data]

Eykman, 1889
Eykman, J.F., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1889, 4, 497. [all data]

Eykman, 1889, 2
Eykman, J.F., Zur kryoskopischen Molekulargewichtsbestimmung, Z. Physik. Chem., 1889, 4, 497-519. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Kiselev, Khuzyasheva, et al., 1979
Kiselev, V.D.; Khuzyasheva, d.G.; Konovalov, A.I., Thermochemical study of the acylation of para-substituted anilines, J. Gen. Chem. USSR, 1979, 49, 2273-2276. [all data]

Chimishkyan, Svetlova, et al., 1984
Chimishkyan, A.L.; Svetlova, L.P.; Leonova, T.V.; Gluyaev, N.D., Thermal decomposition of substituted ureas, J. Gen. Chem. USSR, 1984, 54, 1317-1320. [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]

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]

Potapov and Iskakov, 1971
Potapov, V.K.; Iskakov, L.I., Electronic structure and photoionization of aromatic amines, High Energy Chem., 1971, 5, 237, In original 264. [all data]

Farrell and Newton, 1966
Farrell, P.G.; Newton, J., Ionization potentials of primary aromatic amines and aza-hydrocarbons, Tetrahedron Lett., 1966, 5517. [all data]

Eland, Shepherd, et al., 1966
Eland, J.H.D.; Shepherd, P.J.; Danby, C.J., Ionization potentials of aromatic molecules determined by analytical interpretation of electron impact data, Z. Naturforsch., 1966, 21a, 1580. [all data]

Kinoshita, 1962
Kinoshita, M., The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil, Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]

Briegleb and Czekalla, 1959
Briegleb, G.; Czekalla, J., Die Bestimmung von lonisierungsenergien aus den Spektren von Elektronenubergangskomplexen, Z.Elektrochem., 1959, 63, 6. [all data]

Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Spiers, M.; Ridyard, J.N.A., The electronic structure of substituted benzenes; a study of aniline, the toluidines, phenylenediamines and fluoroanilines by photoelectron spectroscopy and ab initio calculations, J. Mol. Struct., 1979, 53, 235. [all data]

Szepes, Distefano, et al., 1974
Szepes, L.; Distefano, G.; Pignataro, S., Steric inhibition of resonance in acetanilides by UV photoelectron spectroscopy, Ann. Chim., 1974, 64, 159. [all data]

Kobayashi and Nagakura, 1972
Kobayashi, T.; Nagakura, S., Photoelectron spectra of anilines, Chem. Lett., 1972, 1013. [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]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [all data]

Lang (editor), 1961
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1961, 2, 173. [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, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References