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
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry 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:
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

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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:
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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes

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]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Westrum, 1961
Westrum, E.F., Jr., The thermophysical properties of three globular molecules, J. Phys. Chem. Solids, 1961, 18, 83-85. [all data]

Chang and Westrum, 1960
Chang, S.-S.; Westrum, E.F., Jr., Heat capacities and thermodynamic properties of globular molecules. II. Triethylenediamine, J. Phys. Chem., 1960, 64, 1551-1552. [all data]

Trowbridge and Westrum, 1963
Trowbridge, J.C.; Westrum, E.F., Jr., Heat capacities and thermodynamic properties of globular molecules. VII. Transition and fusion of triethylenediamine, J. Phys. Chem., 1963, 67, 2381-2385. [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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  IE (evaluated)	Recommended ionization energy
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions

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