Aniline

• Formula: C₆H₇N
• Molecular weight: 93.1265
• IUPAC Standard InChI: InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 Copy

  
• IUPAC Standard InChIKey: PAYRUJLWNCNPSJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 62-53-3
• 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.
• Isotopologues:
  • Benzen-d5-amine
• Other names: Benzenamine; Aminobenzene; Aminophen; Anyvim; Benzene, amino-; Blue Oil; C.I. 76000; Phenylamine; Aniline Oil; Aniline reagent; Anilin; Anilina; Benzidam; C.I. Oxidation base 1; Cyanol; Huile D'aniline; Krystallin; Kyanol; NCI-C03736; Rcra waste number U012; UN 1547; Benzeneamine
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
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

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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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

Gas phase ion energetics data

Go To: Top, Phase change data, Ion clustering data, References, Notes

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

View reactions leading to C₆H₇N⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₆H₆N^- +  =

By formula: C₆H₆N^- + H⁺ = C₆H₇N

Ion clustering data

Go To: Top, Phase change 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 as indicated in comments:
B - John E. Bartmess
M - 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

 +  = ( • )

By formula: Br^- + C₆H₇N = (Br^- • C₆H₇N)

Free energy of reaction

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₆H₇N = (C₆H₇N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

C₇H₉N⁺ +  = (C₇H₉N⁺ • )

By formula: C₇H₉N⁺ + C₆H₇N = (C₇H₉N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

C₈H₁₁N⁺ +  = (C₈H₁₁N⁺ • )

By formula: C₈H₁₁N⁺ + C₆H₇N = (C₈H₁₁N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

C₉H₁₃N⁺ +  = (C₉H₁₃N⁺ • )

By formula: C₉H₁₃N⁺ + C₆H₇N = (C₉H₁₃N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

 +  = ( • )

By formula: F^- + C₆H₇N = (F^- • C₆H₇N)

 +  = ( • )

By formula: I^- + C₆H₇N = (I^- • C₆H₇N)

 +  = ( • )

By formula: K⁺ + C₆H₇N = (K⁺ • C₆H₇N)

References

Go To: Top, Phase change 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.

Hatton, Hildenbrand, et al., 1962
Hatton, W.E.; Hildenbrand, D.L.; Sinke, G.C.; Stull, D.R., Chemical Thermodynamic Properties of Aniline, J. Chem. Eng. Data, 1962, 7, 229. [all data]

Ziegler and Andrews, 1942
Ziegler, W.T.; Andrews, D.H., The heat capacity of benzene-d6, J. Am. Chem. Soc., 1942, 64, 2482. [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal Data on Organic Compounds. XI. The Heat Capacities, Entropies and Free Energies of Ten Compounds Containing Oxygen or Nitrogen, J. Am. Chem. Soc., 1933, 55, 7, 2733, https://doi.org/10.1021/ja01334a016 . [all data]

Lagutkin and Kuropatkin, 1981
Lagutkin, O.D.; Kuropatkin, E.I., Critical coefficient of compressibility and critical dens. of aniline, Zh. Fiz. Khim., 1981, 55, 1329. [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturation Line: Measurements for Benzenamine, Butylbenzene, sec -Butylbenzene, tert -Butylbenzene, 2,2-Dimethylbutanoic Acid, Tridecafluoroheptanoic Acid, 2-Butyl-2-ethyl-1,3-propanediol, 2,2,4-Trimethyl-1,3-pentanediol, and 1-Chloro-2-propanol, J. Chem. Eng. Data, 2002, 47, 4, 648-666, https://doi.org/10.1021/je010083e . [all data]

Lee, Chen, et al., 1992
Lee, Chang Ha; Chen, Quen; Mohamed, Rahoma S.; Holder, Gerald D., Vapor-liquid equilibria in the system of toluene/aniline, aniline/naphthalene, and naphthalene/quinoline, J. Chem. Eng. Data, 1992, 37, 2, 179-183, https://doi.org/10.1021/je00006a011 . [all data]

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Majer and Svoboda, 1985
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Maher and Smith, 1979
Maher, Patrick J.; Smith, Buford D., A new total pressure vapor-liquid equilibrium apparatus. The ethanol + aniline system at 313.15, 350.81, and 386.67 K, J. Chem. Eng. Data, 1979, 24, 1, 16-22, https://doi.org/10.1021/je60080a022 . [all data]

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Hatton, Hildenbrand, et al., 1962, 2
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Ahmed and Eades, 1972
Ahmed, A.M.I.; Eades, R.G., Proton relaxation in solid aniline and some methyl derivatives, J. Chem. Soc., Faraday Trans. 2, 1972, 68, 2017, https://doi.org/10.1039/f29726802017 . [all data]

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Ziegler, W.T.; Andrews, D.H., The heat capacity of benzene-d6, J. Am. Chem. Soc., 1942, 64, 2482-2485. [all data]

Parks, Huffman, et al., 1933, 2
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [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]

Meek, Sekreta, et al., 1985
Meek, J.T.; Sekreta, E.; Wilson, W.; Viswanathan, K.S.; Reilly, J.P., The laser photoelectron spectrum of gas phase aniline, J. Chem. Phys., 1985, 82, 1741. [all data]

Hager, Smith, et al., 1985
Hager, J.; Smith, M.; Wallace, S., Autoionizing Rydberg structure observed in the vibrationally selective, two-color threshold photoionization spectrum of jet-cooled aniline, J. Chem. Phys., 1985, 83, 4820. [all data]

Smith, Hager, et al., 1984
Smith, M.A.; Hager, J.W.; Wallace, S.C., Two color photoionization spectroscopy of jet cooled aniline: Vibrational frequencies of the aniline X2B1 radical cation, J. Chem. Phys., 1984, 80, 3097. [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]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

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Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W., An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes, Org. Mass Spectrom., 1976, 11, 207. [all data]

Baldwin, Loudon, et al., 1976
Baldwin, M.A.; Loudon, A.G.; Maccoll, A.; Webb, K.S., The nature and fragmentation pathways of the molecular ions of some arylureas, arylthioureas, acetanilides, thioacetanilides and related compounds, Org. Mass Spectrom., 1976, 11, 1181. [all data]

Debies and Rabalais, 1974
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. III. Bonding with Group V substituents, Inorg. Chem., 1974, 13, 308. [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]

Gilbert, Leach, et al., 1973
Gilbert, J.R.; Leach, W.P.; Miller, J.R., Ionisation appearance potential measurements in arene chromium tricarbonyls, J. Organomet. Chem., 1973, 49, 219. [all data]

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Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. II. Seven valence electron substituents, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 355. [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]

Cooks, Bertrand, et al., 1973
Cooks, R.G.; Bertrand, M.; Beynon, J.H.; Rennekamp, M.E.; Setser, D.W., Energy partitioning data as an ion structure probe. Substituted anisoles, J. Am. Chem. Soc., 1973, 95, 1732. [all data]

Johnstone and Mellon, 1972
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Gross, 1972
Gross, M.L., Ion cyclotron resonance spectrometry. A means of evaluating 'kinetic shifts', Org. Mass Spectrom., 1972, 6, 827. [all data]

Potapov and Iskakov, 1971
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Akopyan and Vilesov, 1964
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Terenin, 1961
Terenin, A., Charge transfer in organic solids, induced by light, Proc. Chem. Soc., London, 1961, 321. [all data]

Watanabe and Mottl, 1957
Watanabe, K.; Mottl, J.R., Ionization potentials of ammonia and some amines, J. Chem. Phys., 1957, 26, 1773. [all data]

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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]

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Meeks, J.; Wahlborg, A.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls: Benzoic acid and its derivatives, J. Electron Spectrosc. Relat. Phenom., 1981, 22, 43. [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]

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Kobayashi, T., A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes, Phys. Lett., 1978, 69, 105. [all data]

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Wren, Vogelhuber, et al., 2012
Wren, S.W.; Vogelhuber, K.M.; Ichino, T.; Stanton, J.F.; Lineberger, W.C., Photoelectron Spectroscopy of Anilinide and Acidity of Aniline, J. Phys. Chem. A, 2012, 116, 12, 3118-3123, https://doi.org/10.1021/jp211463r . [all data]

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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]

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Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

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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]

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Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

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Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P., Binding Energies and Stabilities of Potassium Ion Complexes from Studies of Gas Phase Ion Equilibria K+ + M = K+.M, J. Am. Chem. Soc., 1976, 98, 20, 6133, https://doi.org/10.1021/ja00436a011 . [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Zc	Critical compressability factor
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

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