Benzenamine, N,N-dimethyl-

• Formula: C₈H₁₁N
• Molecular weight: 121.1796
• IUPAC Standard InChI: InChI=1S/C8H11N/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3 Copy

  
• IUPAC Standard InChIKey: JLTDJTHDQAWBAV-UHFFFAOYSA-N Copy
• CAS Registry Number: 121-69-7
• 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: Aniline, N,N-dimethyl-; (Dimethylamino)benzene; Dimethylaniline; Dimethylphenylamine; N,N-Dimethylaniline; Versneller NL 63/10; N,N-Dimethylbenzenamine; Dwumetyloanilina; N,N-(Dimethylamino)benzene; N,N-Dimethylphenylamine; NCI-C56428; N,N-Dimethylbenzeneamine; UN 2253; NL 63-10P; NSC 7195; N,N-dimethylanilin
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • IR 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 liquid

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

Ion clustering 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
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^- + C₈H₁₁N = (Br^- • C₈H₁₁N)

Free energy of reaction

C₈H₁₁N⁺ +  = (C₈H₁₁N⁺ • )

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

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

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, Gas phase ion energetics data, Ion clustering data, 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.

Furukawa, Sakiyama, et al., 1982
Furukawa, J.; Sakiyama, M.; Seki, S.; Saito, Y.; Kusano, K., Standard enthalpies of combustion and vaporization of N,N-dimethylaniline, Bull. Chem. Soc. Jpn., 1982, 55, 3329-3330. [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]

de Kolossowsky and Udowenko, 1934
de Kolossowsky, N.; Udowenko, W.W., Determination des chaleurs specifiques des liquides, Compt. rend., 1934, 198, 1394-1395. [all data]

Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W., Specific heat of liquids. II., Zhur. Obshchei Khim., 1934, 4, 1027-1033. [all data]

Radulescu and Jula, 1934
Radulescu, D.; Jula, O., Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen, Z. Phys. Chem., 1934, B26, 390-393. [all data]

Bramley, 1916
Bramley, A., The study of binary mixtures. Part IV. Heats of reaction and specific heats, J. Chem. Soc. (London), 1916, 109, 496-515. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Verevkin, 1997
Verevkin, Sergey P., Thermochemistry of amines: experimental standard molar enthalpies of formation of some aliphatic and aromatic amines, The Journal of Chemical Thermodynamics, 1997, 29, 8, 891-899, https://doi.org/10.1006/jcht.1997.0212 . [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]

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]

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]

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]

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]

Hansen and Undheim, 1975
Hansen, P.E.; Undheim, K., Mass spectrometry of onium compounds. XXIX. Ionisation potential in structure analysis of valence isomers, Acta Chem. Scand., Ser. B, 1975, 29, 221. [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]

Kobayashi, Kobayashi, et al., 1973
Kobayashi, H.; Kobayashi, M.; Kaizu, Y., Molecular complexes of arenetricarbonylchromium, Bull. Chem. Soc. Jpn., 1973, 46, 3109. [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]

Finch, 1964
Finch, A.C.M., Charge-transfer spectra and the ionization energy of azulene, J. Chem. Soc., 1964, 2272. [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]

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]

Foster, 1959
Foster, R., Ionization potentials of electron donors, Nature (London), 1959, 183, 1253. [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]

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

Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted benzenes, Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]

Schafer and Schweig, 1972
Schafer, W.; Schweig, A., Zur Konjugation in aromatischen Aminen und Phosphanen, Angew. Chem., 1972, 84, 898. [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]

Gowenlock, Jones, et al., 1961
Gowenlock, B.G.; Jones, P.P.; Majer, J.R., Bond dissociation energies in some molecules containing alkyl substituted CH₃, NH₂, and OH, J. Chem. Soc. Faraday Trans., 1961, 57, 23. [all data]

Paul and Kebarle, 1991
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]

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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  T	Temperature
  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
  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

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