Ethylenediamine
- Formula: C2H8N2
- Molecular weight: 60.0983
- IUPAC Standard InChIKey: PIICEJLVQHRZGT-UHFFFAOYSA-N
- CAS Registry Number: 107-15-3
- 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: 1,2-Ethanediamine; β-Aminoethylamine; Dimethylenediamine; Ethane-1,2-diamine; 1,2-Diaminoethane; 1,2-Ethylenediamine; H2NCH2CH2NH2; Aethaldiamin; Aethylenediamin; 1,2-Diaminoaethan; 1,2-Diamino-ethaan; 1,2-Diamino-ethano; Ethyleendiamine; Ethylendiamine; NCI-C60402; UN 1604
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Phase change data
Go To: Top, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 391.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 390.29 | K | N/A | Kato and Tanaka, 1989 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tboil | 389.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 390.1 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 391.65 | K | N/A | Anderson and Shimanskaya, 1969 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 284.290 | K | N/A | Messerly, Finke, et al., 1975 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; adiabatic, A=0.03361/K; B=0.00208/K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 613.1 | K | N/A | Wilson, Wilson, et al., 1996 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 66.19 | atm | N/A | Wilson, Wilson, et al., 1996 | Uncertainty assigned by TRC = 0.099 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11. ± 2. | kcal/mol | AVG | N/A | Average of 9 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.077 | 390.1 | N/A | Majer and Svoboda, 1985 | |
10.5 | 318. | A | Stephenson and Malanowski, 1987 | Based on data from 303. to 391. K.; AC |
11.0 | 299. | A,IP | Stephenson and Malanowski, 1987 | Based on data from 284. to 419. K. See also Messerly, Finke, et al., 1975, 2.; AC |
10.9 | 314. | N/A | Hieber and Woerner, 1934 | Based on data from 299. to 390. K. See also Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
299.66 to 390.6 | 4.21797 | 1302.256 | -81.788 | Hieber and Woerner, 1934 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.7 | 263. | IP | Stephenson and Malanowski, 1987 | Based on data from 242. to 278. K. See also Messerly, Finke, et al., 1975, 2.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
5.038 | 284.1 | DSC | Lee, Chang, et al., 1997 | AC |
5.397 | 284.3 | AC | Acree, 1991 | See also Lee, Lien, et al., 1994 and Messerly, Finke, et al., 1975, 2.; AC |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.1165 | 189.0 | crystaline, II | crystaline, I | Messerly, Finke, et al., 1975, 2 | DH |
5.39749 | 284.29 | crystaline, I | liquid | Messerly, Finke, et al., 1975, 2 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.617 | 189.0 | crystaline, II | crystaline, I | Messerly, Finke, et al., 1975, 2 | DH |
18.99 | 284.29 | crystaline, I | liquid | Messerly, Finke, et al., 1975, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change 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
Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 227.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 218.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
227.3 ± 1. | Hahn and Wesdemiotis, 2003 | MM |
225.1 | Wang, Chu, et al., 1999 | KM results obtained from CID of complexes with secondary amines at E(cm) = 0 eV, extrapolated from CID at E(cm) = 0.8, 1.5, 2.0 eV; MM |
226.6 | Wang, Chu, et al., 1999 | KM results obtained from CID of complexes with secondary amines using Fenselau/Wesdemiotis correction; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.6 | PE | Kimura, Katsumata, et al., 1981 | LLK |
9.25 | PE | Kimura, Katsumata, et al., 1981 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH4N+ | 9.56 | CH2NH2 | EI | Burkey, Castelhano, et al., 1983 | LBLHLM |
References
Go To: Top, Phase change 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.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Kato and Tanaka, 1989
Kato, M.; Tanaka, H.,
Vapor-Liquid Equilibrium Determination with a Flow-Type Ebulliometer for Six Binary Systems Made of Alcohol and Amine,
J. Chem. Eng. Data, 1989, 34, 203. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]
Anderson and Shimanskaya, 1969
Anderson, A.A.; Shimanskaya, M.V.,
Gas-Liquid Chromatography of some Aliphatic and Heterocyclic Polyfunctional Amines: II. Solution Thermodyn. of Amines in Fix. Phas.,
Latv. PSR Zinat. Akad. Vestis, Kim. Ser., 1969, No. 5, 527. [all data]
Messerly, Finke, et al., 1975
Messerly, J.F.; Finke, H.L.; Osborn, A.G.; Douslin, D.R.,
Low-temperature calorimetric and vapor-pressure studies on alkanediamines,
J. Chem. Thermodyn., 1975, 7, 1029-46. [all data]
Wilson, Wilson, et al., 1996
Wilson, L.C.; Wilson, H.L.; Wilding, W.V.; Wilson, G.M.,
Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method,
J. Chem. Eng. Data, 1996, 41, 1252-4. [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]
Messerly, Finke, et al., 1975, 2
Messerly, J.F.; Finke, H.L.; Osborn, A.G.; Douslin, D.R.,
Low-temperature calorimetric and vapor-pressure studies on alkanediamines,
J. Chem. Thermodynam., 1975, 7, 1029-1046. [all data]
Hieber and Woerner, 1934
Hieber, W.; Woerner, A.,
Thermochemische Messungen an Komplexbildenden Aminen und Alkoholen,
Zeitschrift für Elektrochemie und angewandte physikalische Chemie, 1934, 40, 5, 252-256, https://doi.org/10.1002/bbpc.19340400508
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Lee, Chang, et al., 1997
Lee, Ming-Jer; Chang, Yao-Kun; Lin, Ho-mu; Chen, Chang-Hsin,
Solid-Liquid Equilibria for 4-Methoxyphenol with Catechol, Ethylenediamine, or Piperazine,
J. Chem. Eng. Data, 1997, 42, 2, 349-352, https://doi.org/10.1021/je960201b
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Lee, Lien, et al., 1994
Lee, Ming-Jer; Lien, Pei-Jung; Huang, Wen-Kuo,
Solid-Liquid Equilibria for Binary Mixtures Containing Cresols, Ethylenediamine, and Anisole,
Ind. Eng. Chem. Res., 1994, 33, 11, 2853-2858, https://doi.org/10.1021/ie00035a040
. [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]
Hahn and Wesdemiotis, 2003
Hahn, I.S.; Wesdemiotis, C.,
Protonation Thermochemistry of beta-Alanine. An Evaluation of Proton Affinities and Entropies Determined by the Extended Kinetic Method,
Int. J. Mass Spectrometry, 2003, 222, 465. [all data]
Wang, Chu, et al., 1999
Wang, Z.; Chu, I.K.; Rodriquez, C.F.; Hopkinson, A.C.; Siu, K.W.M.,
α,ω-Diaminoalkanes as models for bases that dicoordinate the proton: An evaluation of the kinetic method for estimating their proton affinities,
J. Phys. Chem. A., 1999, 103, 8700. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Burkey, Castelhano, et al., 1983
Burkey, T.J.; Castelhano, A.L.; Griller, D.; Lossing, F.P.,
Heats of formation and ionization potentials of some α-aminoalkyl radicals,
J. Am. Chem. Soc., 1983, 105, 4701. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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