p-Aminotoluene

• Formula: C₇H₉N
• Molecular weight: 107.1531
• IUPAC Standard InChI: InChI=1S/C7H9N/c1-6-2-4-7(8)5-3-6/h2-5H,8H2,1H3 Copy

  
• IUPAC Standard InChIKey: RZXMPPFPUUCRFN-UHFFFAOYSA-N Copy
• CAS Registry Number: 106-49-0
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: p-Toluidine; p-Methylaniline; p-Methylbenzenamine; p-Tolylamine; C.I. Azoic coupling component 107; 1-Amino-4-methylbenzene; 4-Aminotoluene; 4-Methylaniline; 4-Methylbenzenamine; 4-Toluidine; Benzenamine, 4-methyl-; 4-Amino-1-methylbenzene; 4-Tolylamine; p-Toluidin; Aniline, p-methyl-; 4-Aminotoluen; Rcra waste number U353; C.I. 37107; Naphtol AS-KG; Naphtol AS-KGLL; NSC 15350
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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.

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

Constant pressure heat capacity of solid

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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

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^- +  =

By formula: C₇H₈N^- + H⁺ = C₇H₉N

 +  =  + 

By formula: C₇H₉N + C₇H₅IO = HI + C₁₄H₁₃NO

 +  =  + 

By formula: C₇H₉N + C₇H₅BrO = HBr + C₁₄H₁₃NO

 +  =  + 

By formula: C₇H₉N + C₇H₅ClO = C₁₄H₁₃NO + HCl

C₁₅H₁₆N₂O =  + 

By formula: C₁₅H₁₆N₂O = C₇H₉N + C₈H₇NO

= 0.5 + 0.5

By formula: C₈H₁₁N = 0.5C₇H₉N + 0.5C₉H₁₃N

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (11% IN CCl4 FOR 3800-1300, 11% IN TMP FOR 1300-650, AND 11% IN CCl4 FOR 650-250 CM^-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

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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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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