Triethylamine

• Formula: C₆H₁₅N
• Molecular weight: 101.1900
• IUPAC Standard InChI: InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 Copy

  
• IUPAC Standard InChIKey: ZMANZCXQSJIPKH-UHFFFAOYSA-N Copy
• CAS Registry Number: 121-44-8
• 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: Ethanamine, N,N-diethyl-; (C2H5)3N; (Diethylamino)ethane; N,N-Diethylethanamine; TEN; Triaethylamin; Trietilamina; UN 1296; 1069-58-5 (maleate); 554-68-7 (chloride)
• 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
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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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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:
LL - Sharon G. Lias and Joel F. Liebman
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

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 by: 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

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₆H₁₅N = (C₃H₉Sn⁺ • C₆H₁₅N)

Free energy of reaction

C₆H₁₆N⁺ +  = (C₆H₁₆N⁺ • )

By formula: C₆H₁₆N⁺ + C₆H₁₅N = (C₆H₁₆N⁺ • C₆H₁₅N)

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.

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Joukovsky, 1934
Joukovsky, N.I., Experimental Study of the Theory of Concentrated Solutions. XI. Thermodynamic Properties of Concentrated Solutions of Aliphatic Organic Compounds Containing Nitrogen., Bull. Soc. Chim. Belg., 1934, 43, 397. [all data]

Timmermans and Hennaut-Roland, 1932
Timmermans, J.; Hennaut-Roland, M., The Work of the International Bureau of Physical-Chemical Standards. V. Study of the Physical Constants of Twenty Organic Compounds., J. Chim. Phys. Phys.-Chim. Biol., 1932, 29, 529-68. [all data]

Timmermans, 1914
Timmermans, J., Freezing temperature of organic compounds. II., Bull. Soc. Chim. Belg., 1914, 27, 334. [all data]

Herz and Neukirch, 1923
Herz, W.; Neukirch, E., On Knowldge of the Critical State, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1923, 104, 433-50. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Mokbel, Razzouk, et al., 2009
Mokbel, Ilham; Razzouk, Antonio; Sawaya, Terufat; Jose, Jacques, Experimental Vapor Pressures of 2-Phenylethylamine, Benzylamine, Triethylamine, and cis -2,6-Dimethylpiperidine in the Range between 0.2 Pa and 75 kPa, J. Chem. Eng. Data, 2009, 54, 3, 819-822, https://doi.org/10.1021/je800603z . [all data]

WANG, FANG, et al., 2006
WANG, Z.; FANG, W.; LIN, R.; GUO, Y.; ZHOU, X., Volatility of blended fuel of endothermic hydrocarbon fuel and triethylamine, Fuel, 2006, 85, 12-13, 1794-1797, https://doi.org/10.1016/j.fuel.2006.02.011 . [all data]

Baev, 2001
Baev, A.K., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 2001, 44, 1, 3. [all data]

Dutt, Kahol, et al., 1990
Dutt, N.V.K.; Kahol, A.P.; Reddy, P.J.; Raghunandanan, K.S., Isobaric vapor-liquid equilibria for the binary systems of benzene/triethylamine, benzene/trimethyl phosphite, and triethylamine/trimethyl phosphite, J. Chem. Eng. Data, 1990, 35, 2, 114-117, https://doi.org/10.1021/je00060a004 . [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]

Majer, Svoboda, et al., 1979
Majer, Vladimír; Svoboda, Václav; Koubek, Josef; Pick, Jirí, Temperature dependence of heats of vaporization, saturated vapour pressures and cohesive energies for a group of amines, Collect. Czech. Chem. Commun., 1979, 44, 12, 3521-3528, https://doi.org/10.1135/cccc19793521 . [all data]

Bayles and Letcher, 1971
Bayles, John W.; Letcher, Trevor M., Thermodynamics of some binary liquid mixtures containing aliphatic amines, J. Chem. Eng. Data, 1971, 16, 3, 266-271, https://doi.org/10.1021/je60050a026 . [all data]

Thompson and Linnett, 1936
Thompson, H.W.; Linnett, J.W., The vapour pressures and association of some metallic and non-metallic alkyls, Trans. Faraday Soc., 1936, 32, 681, https://doi.org/10.1039/tf9363200681 . [all data]

Thompson and Linnett, 1936, 2
Thompson, H.W.; Linnett, J.W., The vapour pressures and association of some metallic and non-metallic alkyls, Trans. Faraday Soc., 1936, 32, 681-685. [all data]

Bittrich and Kauer, 1962
Bittrich, H.J.; Kauer, E., Zur Thermodynamik des Systems Diathylamin-Triathylamin. I. Das Flussigkeits-Dampf-Gleichgewicht, Z. Phys. Chem. (Frankfurt/Main), 1962, 219, 224-238. [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]

Mathis and Compton, 1996
Mathis, J.E.; Compton, R.N., Single and multiple photon ionization of triethylamine, J. Chem. Phys., 1996, 104, 8341. [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T., Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines, J. Am. Chem. Soc., 1976, 98, 311. [all data]

Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T., Photoelectron spectrum and gas-phase basicity of manxine. Evidence for a planar bridgehead nitrogen, J. Am. Chem. Soc., 1975, 97, 4136. [all data]

Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W., Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials, J. Chem. Soc., 1964, 4434. [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]

Zverev and Titova, 1996
Zverev, V.V.; Titova, Z.S., Theoretical and experimental investigation of stereoelectronic interactions in H-complexes of sulfenamide derivatives, Izv. Akad. Nauk Ser. Khim., 1996, 2894. [all data]

Utsunomiya, Kobayashi, et al., 1976
Utsunomiya, C.; Kobayashi, T.; Nagakura, S., Photoelectron spectra of electron donor-acceptor complexes between bromine and alkylamines, Chem. Phys. Lett., 1976, 39, 245. [all data]

Leavell, Steichen, et al., 1973
Leavell, S.; Steichen, J.; Franklin, J.L., Photoelectron spectra of intramolecularly hydrogen bonded compounds, J. Chem. Phys., 1973, 59, 4343. [all data]

SenSharma and Franklin, 1973
SenSharma, D.K.; Franklin, J.L., Heat of formation of free radicals by mass spectrometry, J. Am. Chem. Soc., 1973, 95, 6562. [all data]

Plotnikov, Bogolyubov, et al., 1969
Plotnikov, V.F.; Bogolyubov, G.M.; Maretina, I.A.; Petrov, A.A., Organic derivatives of elements of Groups V and VI. V. Mass spectra of 1-buten-3-ynylamines, Zh. Org. Khim., 1969, 5, 1137, In original 1157. [all data]

Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH₃)₃Sn⁺ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

Meot-Ner M. and Sieck, 1983
Meot-Ner M.; Sieck, L.W., The Ionic Hydrogen Bond. 1. Sterically Hindered Bonds. Solvation and Clustering of Sterically Hindered Amines and Pyridines, J. Am. Chem. Soc., 1983, 105, 10, 2956, https://doi.org/10.1021/ja00348a005 . [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
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  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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