p-Aminotoluene

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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 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
Δfgas41.8kJ/molCcbDraeger, 1984ALS
Δfgas62.2kJ/molN/APushin, 1954Value computed using ΔfHliquid° value of 19 kj/mol from Pushin, 1954 and ΔvapH° 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
Δfliquid19.kJ/molCcbPushin, 1954Author's hf298_condensed=1.8 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-4059.kJ/molCcbPushin, 1954Author's hf298_condensed=1.8 kcal/mol; ALS
Δcliquid-4061.4kJ/molCcbSwarts, 1909ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
165.2298.15Meva'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
124.3293.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
Pc23.8114barN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2.0265 bar; TRC
Quantity Value Units Method Reference Comment
Δvap57.8 ± 0.3kJ/molGSEmel'yanenk and Verevkin, 2005Based on data from 319. to 345. K.; AC
Δvap43.18kJ/molCGlaser and Ruland, 1957ALS
Δvap62.1kJ/molN/AGlaser and Rüland, 1957Based on data from 474. to 641. K. See also Emel'yanenk and Verevkin, 2005.; AC
Δvap55.9kJ/molEBBerliner and May, 1927Based on data from 313. to 473. K. See also Emel'yanenk and Verevkin, 2005.; AC
Quantity Value Units Method Reference Comment
Δsub76.2 ± 0.3kJ/molGSEmel'yanenk and Verevkin, 2005Based on data from 284. to 313. K.; AC
Δsub78.8 ± 0.5kJ/molN/AChao, Gadalla, et al., 1990AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
51.1408.AStephenson and Malanowski, 1987Based on data from 393. to 474. K.; AC
54.9330.N/AStull, 1947Based on data from 315. to 473. K.; 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
315. to 473.64.718841961.716-57.00Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
17.300316.55Meva'a and Lichanot, 1990DH
17.19317.Censký, Lipovská, et al., 2001AC
17.89316.5Acree, 1991AC
17.3316.6Meva'a and Lichanot, 1990AC
18.9316.9Rastogi, Nigam, et al., 1963AC
17.28315.6Eykman, 1889AC
17.280315.6Eykman, 1889, 2DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
55.316.55Meva'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:


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)896.7kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity864.8kJ/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
Δr1537. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1507. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]

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]

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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References