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
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Gas phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 90.4 ± 6.7 | kJ/mol | Ccr | Rapport, Westrum, et al., 1971 | Author was aware that data differs from previously reported values; ALS |
ΔfH°gas | 48.0 | kJ/mol | N/A | Parris, Raybin, et al., 1964 | Value computed using ΔfHsolid° value of -14.2±8.4 kj/mol from Parris, Raybin, et al., 1964 and ΔsubH° value of 62.2 kj/mol from Rapport, Westrum, et al., 1971.; DRB |
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
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 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 62.2 | kJ/mol | N/A | Rapport, Westrum, et al., 1971 | DRB |
ΔsubH° | 61.9 | kJ/mol | V | Wada, Kishida, et al., 1960 | ALS |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
54.4 | 348. | Bondi, 1963 | Based on data from 323. to 373. K.; AC |
61.9 ± 3.3 | 338. | Wada, Kishida, et al., 1960, 2 | Based on data from 324. to 351. K. See also Cox and Pilcher, 1970.; AC |
52.3 ± 3.3 | 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 (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.45 | 433. | Domalski and Hearing, 1996 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
10.560 | 351.08 | crystaline, II | crystaline, I | Trowbridge and Westrum, 1963, 2 | Transformation to plastic crystalline phase.; DH |
7.431 | 432.99 | crystaline, I | liquid | Trowbridge and Westrum, 1963, 2 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
30.08 | 351.08 | crystaline, II | crystaline, I | Trowbridge and Westrum, 1963, 2 | Transformation; DH |
17.16 | 432.99 | crystaline, I | liquid | Trowbridge and Westrum, 1963, 2 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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) | 963.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 934.6 | kJ/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 |
IR Spectrum
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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: Coblentz Society, Inc.
Condensed Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | COBLENTZ SOC. Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | WESTERN REGIONAL RES. USDA |
Source reference | COBLENTZ NO. 05852 |
Date | 1966/02/24 |
Name(s) | 1,4-diazabicyclo[2.2.2]octane |
State | SOLUTION (10% CCl4 FOR 4000-1200, 10% CS2 FOR 1200-450 CM-1) VS SOLVENT |
Instrument | CARY 90 (GRATING) |
Instrument parameters | ORDER CHANGES: 3000, 2000, 1200 CM-1 |
Path length | 0.010 CM, AND 0.011 CM |
Resolution | 2 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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
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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 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PMS-100 | 130. | 1018. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 150. | 1023. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 180. | 1040. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 152. | 1520. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 1535. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 180. | 1531. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1548. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1548. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]
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
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]
Trowbridge and Westrum, 1963, 2
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[4.4.1.13,8]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]
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
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfH°gas Enthalpy of formation of gas 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
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