Triethylenediamine

• Formula: C₆H₁₂N₂
• Molecular weight: 112.1729
• IUPAC Standard InChI: InChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2 Copy

  
• IUPAC Standard InChIKey: IMNIMPAHZVJRPE-UHFFFAOYSA-N Copy
• CAS Registry Number: 280-57-9
• 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: 1,4-Diazabicyclo[2.2.2]octane; Bicyclo[2.2.2]-1,4-diazaoctane; D 33LV; Dabco; Dabco 33LV; N,N'-endo-Ethylenepiperazine; 1,4-Diaza[2.2.2]bicyclooctane; 1,4-Ethylenepiperazine; Dabco R-8020; Dabco S-25; Dabco crystalline; TEDA-L33; Tegoamin 33; Texacat TD-33; Bicyclo[2.2.2]octane, 1,4-diaza-; Dabco Crystal; NSC 56362; TED; TEDA; Texacat TD 100; 1,4-diazabicyclooctane; 1,4 Diazabicyclo (2,2,2)octane
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• Information on this page:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• 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.

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
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

Ionization energy determinations

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Rapport, Westrum, et al., 1971
Rapport, N.J.; Westrum, E.F., Jr.; Andrews, J.T.S., Enthalpies of formation for globular molecules. III. Succinonitrile and triethylenediamine, J. Am. Chem. Soc., 1971, 93, 4363-4365. [all data]

Parris, Raybin, et al., 1964
Parris, M.; Raybin, P.S.; Labowitz, L.C., Enthalpy of combustion and related thermodynamic properties of triethylenediamine, J. Chem. Eng. Data, 1964, 9, 221-223. [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]

Boogaarts, Holleman, et al., 1996
Boogaarts, M.G.H.; Holleman, I.; Jongma, R.T.; Parker, D.H.; Meijer, G.; Even, U., High Rydberg states of DABCO: Spectroscopy, ionization potential, and comparison with mass analyzed threshold ionization, J. Chem. Phys., 1996, 104, 4357. [all data]

Smith, Hager, et al., 1984
Smith, M.A.; Hager, J.W.; Wallace, S.C., Two-color laser photoionization spectroscopy in a collisionless free-jet expansion: Spectroscopy and excited-state dynamics of diazabicyclooctane, J. Phys. Chem., 1984, 88, 2250. [all data]

Parker and El-Sayed, 1979
Parker, D.H.; El-Sayed, M.A., Determination of excited state lifetimes and ionization potentials by dual beam visible lasars, Chem. Phys., 1979, 42, 379. [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]

Nelsen and Buschek, 1974
Nelsen, S.F.; Buschek, J.M., Photoelectron spectra of some cyclic di- and polyamines. Lone pair-lone pair interaction in 1,3- and 1,4-diamines, J. Am. Chem. Soc., 1974, 96, 7930. [all data]

Nelsen and Buschek, 1974, 2
Nelsen, S.F.; Buschek, J.M., Charge delocalization in saturated systems. The radical cation of 1,3,6,8-tetraazatricyclo[4.4.1.1^3,8]dodecane, J. Am. Chem. Soc., 1974, 96, 6424. [all data]

Hamada, Hirakawa, et al., 1973
Hamada, Y.; Hirakawa, A.Y.; Tsuboi, M.; Ogata, H., Interaction between lone pair electrons on the nitrogen atoms in 1,5-diazabicyclo[3.2.1]octane, Bull. Chem. Soc. Jpn., 1973, 46, 2244. [all data]

Heilbronner and Muszkat, 1970
Heilbronner, E.; Muszkat, K.A., On the relative importance of through-space vs. through-bond interaction between the lone pairs in 1,4-diazabicyclo[2.2.2.]octane, J. Am. Chem. Soc., 1970, 92, 3818. [all data]

Bischof, Hashmall, et al., 1969
Bischof, P.; Hashmall, J.A.; Heilbronner, E.; Hornung, V., Nitrogen lone pair interaction in 1,4-diaza-bicyclo[2.2.2]octane (DABCO), Tetrahedron Lett., 1969, 4025. [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Notes

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• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  ΔfH°gas	Enthalpy of formation of gas at standard conditions

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