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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -17.0 ± 0.59 | kJ/mol | Ccr | Good and Moore, 1970 |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -63.01 ± 0.54 | kJ/mol | Ccr | Good and Moore, 1970 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1867.3 ± 0.50 | kJ/mol | Ccr | Good and Moore, 1970 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 202.42 | J/mol*K | N/A | Messerly, Finke, et al., 1975 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
172.59 | 298.15 | Messerly, Finke, et al., 1975 | T = 11 to 335 K.; DH |
178.7 | 313. | Hough, Mason, et al., 1950 | T = 313 to 333 K.; DH |
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:
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, 2 | 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 | 67.07 | bar | N/A | Wilson, Wilson, et al., 1996 | Uncertainty assigned by TRC = 0.10 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 46. ± 6. | kJ/mol | AVG | N/A | Average of 9 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
37.98 | 390.1 | N/A | Majer and Svoboda, 1985 | |
43.9 | 318. | A | Stephenson and Malanowski, 1987 | Based on data from 303. to 391. K.; AC |
45.9 | 299. | A,IP | Stephenson and Malanowski, 1987 | Based on data from 284. to 419. K. See also Messerly, Finke, et al., 1975.; AC |
45.6 | 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 (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
299.66 to 390.6 | 4.22368 | 1302.256 | -81.788 | Hieber and Woerner, 1934 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
65.6 | 263. | IP | Stephenson and Malanowski, 1987 | Based on data from 242. to 278. K. See also Messerly, Finke, et al., 1975.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.08 | 284.1 | DSC | Lee, Chang, et al., 1997 | AC |
22.58 | 284.3 | AC | Acree, 1991 | See also Lee, Lien, et al., 1994 and Messerly, Finke, et al., 1975.; AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.4874 | 189.0 | crystaline, II | crystaline, I | Messerly, Finke, et al., 1975 | DH |
22.5831 | 284.29 | crystaline, I | liquid | Messerly, Finke, et al., 1975 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.58 | 189.0 | crystaline, II | crystaline, I | Messerly, Finke, et al., 1975 | DH |
79.44 | 284.29 | crystaline, I | liquid | Messerly, Finke, et al., 1975 | DH |
Reaction 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
By formula: (K+ • 2C2H8N2) + C2H8N2 = (K+ • 3C2H8N2)
Bond type: Polydentate bonding in non-hydrogen-bonded positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 54.0 | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: (K+ • C2H8N2) + C2H8N2 = (K+ • 2C2H8N2)
Bond type: Polydentate bonding in non-hydrogen-bonded positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 92.9 | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 134. | J/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: (C2H9N+ • 2C2H8N2) + C2H8N2 = (C2H9N+ • 3C2H8N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 73.2 | kJ/mol | HPMS | Wincel and Herman, 1973 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 199. | J/mol*K | HPMS | Wincel and Herman, 1973 | gas phase; Entropy change is questionable; M |
By formula: K+ + C2H8N2 = (K+ • C2H8N2)
Bond type: Polydentate bonding in non-hydrogen-bonded positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 108. | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 93.3 | J/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: C2H8N2 + C2H5N = C4H13N3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 82.8 ± 5.0 | kJ/mol | Cm | Dalin, Bobylev, et al., 1988 | liquid phase; solvent: Aqueous HCl; Kinetic; ALS |
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
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) | 951.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 912.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
951. ± 4. | Hahn and Wesdemiotis, 2003 | MM |
941.8 | 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 |
948.1 | 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 |
Ion clustering 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 by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: (C2H9N+ • 2C2H8N2) + C2H8N2 = (C2H9N+ • 3C2H8N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 73.2 | kJ/mol | HPMS | Wincel and Herman, 1973 | gas phase; Entropy change is questionable |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 199. | J/mol*K | HPMS | Wincel and Herman, 1973 | gas phase; Entropy change is questionable |
By formula: K+ + C2H8N2 = (K+ • C2H8N2)
Bond type: Polydentate bonding in non-hydrogen-bonded positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 108. | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 93.3 | J/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase |
By formula: (K+ • C2H8N2) + C2H8N2 = (K+ • 2C2H8N2)
Bond type: Polydentate bonding in non-hydrogen-bonded positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 92.9 | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 134. | J/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase |
By formula: (K+ • 2C2H8N2) + C2H8N2 = (K+ • 3C2H8N2)
Bond type: Polydentate bonding in non-hydrogen-bonded positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 54.0 | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Good and Moore, 1970
Good, W.D.; Moore, R.T.,
Enthalpies of formation of ethylenediamine, 1,2,-propanediamine, 1,2,-butanediamine, 2-methyl-1,2-propanediamine, and isobutylamine C-N and N-F Thermochemical bond energies,
J. Chem. Eng. Data, 1970, 15, 150-154. [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. Thermodynam., 1975, 7, 1029-1046. [all data]
Hough, Mason, et al., 1950
Hough, E.W.; Mason, D.M.; Sage, B.H.,
Heat capacities of several organic liquids,
J. Am. Chem. Soc., 1950, 72, 5775-5777. [all data]
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, 2
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]
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]
Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P.,
Binding Energies and Stabilities of Potassium Ion Complexes with Ethylene Diamine and Dimethoxyethane (Glyme) from Measurements of the Complexing Equilibria in the Gas Phase,
Can. J. Chem., 1976, 54, 16, 2594, https://doi.org/10.1139/v76-368
. [all data]
Wincel and Herman, 1973
Wincel, H.; Herman, J.A.,
Photoionization Study of Clustering Reactions in Diamines: Ethane-1,2-diamine, Propane-1,2-diamine and Propane-1,3-diamine,
J. Chem. Soc. Faraday Trans., 1973, 69, 1797, https://doi.org/10.1039/f19736901797
. [all data]
Dalin, Bobylev, et al., 1988
Dalin, A.R.; Bobylev, V.A.; Suslikov, V.F.; Kamskaya, O.I.; Tereshchenko, G.F.,
Nucleophilic cleavage and the formation of saturated heterocycles. VII. Kinetic and thermochemical study of reactions of aziridine with ethylene amines,
J. Gen. Chem. USSR, 1988, 58, 1868-1871. [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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions 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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