Triethylenediamine
- Formula: C6H12N2
- Molecular weight: 112.1729
- IUPAC Standard InChIKey: IMNIMPAHZVJRPE-UHFFFAOYSA-N
- 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 6.75 ± 0.88 | kcal/mol | Ccr | Rapport, Westrum, et al., 1971 | Author was aware that data differs from previously reported values; ALS |
ΔfH°solid | -3.4 ± 2.0 | kcal/mol | Ccb | Parris, Raybin, et al., 1964 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -3.2 ± 2.2 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -980.95 ± 0.86 | kcal/mol | Ccr | Rapport, Westrum, et al., 1971 | Author was aware that data differs from previously reported values; ALS |
ΔcH°solid | -970.8 ± 2.0 | kcal/mol | Ccb | Parris, Raybin, et al., 1964 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 37.670 | cal/mol*K | N/A | Westrum, 1961 | DH |
S°solid,1 bar | 37.670 | cal/mol*K | N/A | Chang and Westrum, 1960 | DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
36.800 | 300. | Trowbridge and Westrum, 1963 | crystaline, II phase; T = 300 to 450 K.; DH |
36.611 | 298.15 | Westrum, 1961 | T = 5 to 350 K. Only value at 298.15 K given.; DH |
36.561 | 298.15 | Chang and Westrum, 1960 | T = 5 to 353 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 447.15 | K | N/A | Farkas, Mills, et al., 1959 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 431.15 | K | N/A | Farkas, Mills, et al., 1959 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 432.99 | K | N/A | Trowbridge and Westrum, 1963, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 14.9 | kcal/mol | N/A | Rapport, Westrum, et al., 1971 | DRB |
ΔsubH° | 14.8 | kcal/mol | V | Wada, Kishida, et al., 1960 | ALS |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.0 | 348. | Bondi, 1963 | Based on data from 323. to 373. K.; AC |
14.8 ± 0.79 | 338. | Wada, Kishida, et al., 1960, 2 | Based on data from 324. to 351. K. See also Cox and Pilcher, 1970.; AC |
12.5 ± 0.79 | 361. | Wada, Kishida, et al., 1960, 2 | Based on data from 353. to 369. K. See also Cox and Pilcher, 1970.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.78 | 433. | Domalski and Hearing, 1996 | AC |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.5239 | 351.08 | crystaline, II | crystaline, I | Trowbridge and Westrum, 1963 | Transformation to plastic crystalline phase.; DH |
1.776 | 432.99 | crystaline, I | liquid | Trowbridge and Westrum, 1963 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
7.189 | 351.08 | crystaline, II | crystaline, I | Trowbridge and Westrum, 1963 | Transformation; DH |
4.101 | 432.99 | crystaline, I | liquid | Trowbridge and Westrum, 1963 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.321 ± 0.001 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 230.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 223.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.321155 ± 0.000005 | S | Boogaarts, Holleman, et al., 1996 | LL |
7.197 ± 0.001 | S | Smith, Hager, et al., 1984 | LBLHLM |
7.20 | PI | Parker and El-Sayed, 1979 | LLK |
7.52 ± 0.02 | PE | Aue, Webb, et al., 1976 | Vertical value; LLK |
7.61 | PE | Nelsen and Buschek, 1974 | Vertical value; LLK |
7.609 | PE | Nelsen and Buschek, 1974, 2 | Vertical value; LLK |
7.70 | PE | Hamada, Hirakawa, et al., 1973 | Vertical value; LLK |
7.52 | PE | Heilbronner and Muszkat, 1970 | Vertical value; RDSH |
7.52 | PE | Bischof, Hashmall, et al., 1969 | Vertical value; RDSH |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1392 |
NIST MS number | 228321 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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.
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]
Farkas, Mills, et al., 1959
Farkas, A.; Mills, G.A.; Erner, W.E.; Maerker, J.B.,
Triethylenediamine. Physical, Chemical, and Catalytic Properties,
J. Chem. Eng. Data, 1959, 4, 334. [all data]
Trowbridge and Westrum, 1963, 2
Trowbridge, J.C.; Westrum, E.F.,
Heat capacities and thermodynamic properties of globular molecules. VII. Transition and fusion of triethylenediamine,
J. Phys. Chem., 1963, 67, 2381-5. [all data]
Wada, Kishida, et al., 1960
Wada, T.; Kishida, E.; Tomhe, Y.; Suga, H.; Seki, S.; Nitta, I.,
Crystal structure and thermodynamical investigations of triethylenediamine, C6H12N2,
Bull. Chem. Soc. Jpn., 1960, 33, 1317. [all data]
Bondi, 1963
Bondi, A.,
Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments.,
J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027
. [all data]
Wada, Kishida, et al., 1960, 2
Wada, Tadayoshi; Kishida, Etsuko; Tomiie, Yujiro; Suga, Hiroshi; Seki, Syûzô; Nitta, Isamu,
Crystal Structure and Thermodynamical Investigations of Triethylenediamine, C6H12N2,
Bull. Chem. Soc. Jpn., 1960, 33, 9, 1317-1318, https://doi.org/10.1246/bcsj.33.1317
. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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[4.4.1.13,8]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, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.