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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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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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° | 12.9 | kcal/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 26.3 | cal/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° | 22.2 | kcal/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 32.0 | cal/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: (C2H9N+ • 2C2H8N2) + C2H8N2 = (C2H9N+ • 3C2H8N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.5 | kcal/mol | HPMS | Wincel and Herman, 1973 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 47.6 | cal/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° | 25.7 | kcal/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22.3 | cal/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: C2H8N2 + C2H5N = C4H13N3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 19.8 ± 1.2 | kcal/mol | Cm | Dalin, Bobylev, et al., 1988 | liquid phase; solvent: Aqueous HCl; Kinetic; ALS |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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
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 |
Gas Chromatography
Go To: Top, Reaction 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 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 | 150. | 625. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 180. | 612. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 200. | 600. | 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 | 150. | 1195. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 152. | 1265. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 1235. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 180. | 1192. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1183. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1220. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-Wax | 1233. | Peng, 2000 | 15. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
Peng, 2000
Peng, C.T.,
Prediction of retention indices. V. Influence of electronic effects and column polarity on retention index,
J. Chromatogr. A, 2000, 903, 1-2, 117-143, https://doi.org/10.1016/S0021-9673(00)00901-8
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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