1,2-Ethanediol
- Formula: C2H6O2
- Molecular weight: 62.0678
- IUPAC Standard InChIKey: LYCAIKOWRPUZTN-UHFFFAOYSA-N
- CAS Registry Number: 107-21-1
- 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. - Species with the same structure:
- Other names: Ethylene glycol; Ethylene alcohol; Glycol; Glycol alcohol; Lutrol 9; Macrogol 400 BPC; Monoethylene glycol; Ramp; Tescol; 1,2-Dihydroxyethane; 2-Hydroxyethanol; HOCH2CH2OH; Aethylenglykol; Ethane-1,2-diol; Fridex; MEG 100; 1,2-Ethandiol; Ucar 17; Dowtherm SR 1; Norkool; Zerex; Ilexan E; 1,2-Ethylene glycol; 146AR; Ethylene dihydrate; NSC 93876; Union Carbide XL 54 Type I De-icing Fluid; Dihydroxyethane; Ethanediol; Ethylene gycol; Glygen; Athylenglykol; M.e.g.; Aliphatic diol
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Gas phase thermochemistry data
Go To: Top, Reaction 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -394.4 ± 2.8 | kJ/mol | Ccr | Knauth and Sabbah, 1990 | see Knauth and Sabbah, 1989; ALS |
ΔfH°gas | -388. ± 2. | kJ/mol | Ccb | Gardner and Hussain, 1972 | ALS |
ΔfH°gas | -390.3 | kJ/mol | N/A | McClaine, 1947 | Value computed using ΔfHliquid° value of -455.9 kj/mol from McClaine, 1947 and ΔvapH° value of 65.6 kj/mol from Knauth and Sabbah, 1990.; DRB |
ΔfH°gas | -389.3 | kJ/mol | N/A | Parks, West, et al., 1946 | Value computed using ΔfHliquid° value of -454.9±0.3 kj/mol from Parks, West, et al., 1946 and ΔvapH° value of 65.6 kj/mol from Knauth and Sabbah, 1990.; DRB |
ΔfH°gas | -387.5 | kJ/mol | N/A | Moureu and Dode, 1937 | Value computed using ΔfHliquid° value of -453.1±1.2 kj/mol from Moureu and Dode, 1937 and ΔvapH° value of 65.6 kj/mol from Knauth and Sabbah, 1990.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 311.84 | J/mol*K | N/A | Chao J., 1986 | Other third-law entropy values at 298.15 K known from literature are 284.5 [ Buckley P., 1967], 312.5 [ Stull D.R., 1969], and 315.47(5.36) J/mol*K [ Yeh T.-S., 1994].; GT |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
59.79 | 200. | Yeh T.-S., 1994 | Other statistically calculated values of entropy at 298.15 K (274.76 [ Buckley P., 1967], 293.76 [ Frei H., 1977], 303.8 [ Chao J., 1986], and 323.55 J/mol*K [ Dyatkina M.E., 1954]) are in worse agreement with third-law entropy value.; GT |
77.99 | 298.15 | ||
78.41 | 300. | ||
97.99 | 400. | ||
113.64 | 500. | ||
125.65 | 600. | ||
135.23 | 700. | ||
143.26 | 800. | ||
150.25 | 900. | ||
156.40 | 1000. |
Reaction thermochemistry data
Go To: Top, Gas 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:
B - John E. Bartmess
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: (Cl- • C2H6O2) + C2H6O2 = (Cl- • 2C2H6O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.5 ± 5.0 | kJ/mol | TDAs | Zhang, Beglinger, et al., 1995 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 39. ± 4.2 | kJ/mol | TDAs | Zhang, Beglinger, et al., 1995 | gas phase; B |
By formula: Cl- + C2H6O2 = (Cl- • C2H6O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 106. ± 4.2 | kJ/mol | TDAs | Zhang, Beglinger, et al., 1995 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 69.5 ± 4.2 | kJ/mol | TDAs | Zhang, Beglinger, et al., 1995 | gas phase; B |
C2H5O2- + =
By formula: C2H5O2- + H+ = C2H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1528. ± 10. | kJ/mol | G+TS | Crowder and Bartmess, 1993 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1510. ± 8.4 | kJ/mol | IMRE | Crowder and Bartmess, 1993 | gas phase; B |
By formula: C2H6O2 + C3H6O = C5H10O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -10. | kJ/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
By formula: C2H6O2 + HNO3 = C2H5NO4 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.9 | kJ/mol | Cm | Tsvetkov, Sopin, et al., 1986 | liquid phase; ALS |
+
= C2H6NO3-
By formula: NO- + C2H6O2 = C2H6NO3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 113.0 | kJ/mol | N/A | Hendricks, de Clercq, et al., 2002 | gas phase; B |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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
Data compiled as indicated in comments:
B - John E. Bartmess
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
View reactions leading to C2H6O2+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 815.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 773.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.16 | EI | Holmes and Lossing, 1982 | LBLHLM |
10.55 | PE | Ohno, Imai, et al., 1985 | Vertical value; LBLHLM |
10.55 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.5 | PE | Von Niessen, Bieri, et al., 1980 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3O+ | 11.12 ± 0.05 | CH2OH | EI | Holmes and Lossing, 1984 | LBLHLM |
CH3O+ | 12.5 ± 0.15 | CH2O+H | EI | Holmes, Lossing, et al., 1983 | LBLHLM |
CH4O+[CH2OH2+] | 11.42 ± 0.05 | CH2O | EI | Holmes, Lossing, et al., 1982 | LBLHLM |
CH5O+[CH3OH2+] | 10.7 ± 0.1 | CHO | EI | Burgers, Holmes, et al., 1987 | LBLHLM |
De-protonation reactions
C2H5O2- + =
By formula: C2H5O2- + H+ = C2H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1528. ± 10. | kJ/mol | G+TS | Crowder and Bartmess, 1993 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1510. ± 8.4 | kJ/mol | IMRE | Crowder and Bartmess, 1993 | gas phase; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, 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
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 | NIST Mass Spectrometry Data Center |
NIST MS number | 341866 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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.
Knauth and Sabbah, 1990
Knauth, P.; Sabbah, R.,
Energetics of intra- and intermolecular bonds in ω-alkanediols (II) Thermochemical study of 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, and 1,5-pentanediol at 298.15K,
Struct. Chem., 1990, 1, 43-46. [all data]
Knauth and Sabbah, 1989
Knauth, P.; Sabbah, R.,
Combustion calorimetry on milligram samples of liquid substances with a CRMT rocking bomb calorimeter. Application to the study of ω-alkanediol at 298.15 K,
J. Chem. Thermodyn., 1989, 21, 203-210. [all data]
Gardner and Hussain, 1972
Gardner, P.J.; Hussain, K.S.,
The standard enthalpies of formation of some aliphatic diols,
J. Chem. Thermodyn., 1972, 4, 819-827. [all data]
McClaine, 1947
McClaine, L.A.,
Thermodynamic data for some compounds containing carbon, hydrogen and oxygen, Ph.D. Thesis for Stanford University, 1947, 1-57. [all data]
Parks, West, et al., 1946
Parks, G.S.; West, T.J.; Naylor, B.F.; Fujii, P.S.; McClaine, L.A.,
Thermal data on organic compounds. XXIII. Modern combustion data for fourteen hydrocarbons and five polyhydroxy alcohols,
J. Am. Chem. Soc., 1946, 68, 2524-2527. [all data]
Moureu and Dode, 1937
Moureu, H.; Dode, M.,
Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues,
Bull. Soc. Chim. France, 1937, 4, 637-647. [all data]
Chao J., 1986
Chao J.,
Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties,
J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]
Buckley P., 1967
Buckley P.,
Infrared studies on rotational isomerism. I. Ethylene glycol,
Can. J. Chem., 1967, 45, 397-407. [all data]
Stull D.R., 1969
Stull D.R., Jr.,
The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]
Yeh T.-S., 1994
Yeh T.-S.,
Global conformational analysis of 1,2-ethanediol,
J. Phys. Chem., 1994, 98, 8921-8929. [all data]
Frei H., 1977
Frei H.,
Ethylene glycol: infrared spectra, ab initio calculation, vibrational analysis and conformations of 5 matrix isolated isotopic modifications,
Chem. Phys., 1977, 25, 271-298. [all data]
Dyatkina M.E., 1954
Dyatkina M.E.,
Thermodynamic functions of normal alcohols (propanol, butanol, ethylene glycol),
Zh. Fiz. Khim., 1954, 28, 377. [all data]
Zhang, Beglinger, et al., 1995
Zhang, W.; Beglinger, C.; Stone, J.A.,
High-pressure mass spectrometric study of the gas-phase association of Cl- with alpha,omega-diols,
J. Phys. Chem., 1995, 99, 30, 11673, https://doi.org/10.1021/j100030a009
. [all data]
Crowder and Bartmess, 1993
Crowder, C.; Bartmess, J.,
The Gas Phase Acidities of Diols,
J. Am. Soc. Mass Spectrom., 1993, 4, 9, 723, https://doi.org/10.1016/1044-0305(93)80051-Y
. [all data]
Anteunis and Rommelaere, 1970
Anteunis, M.; Rommelaere, Y.,
NMR experiments on acetals. XXIX. The ease of acetonide formation of some glycols,
Bull. Soc. Chim. Belg., 1970, 79, 523-530. [all data]
Tsvetkov, Sopin, et al., 1986
Tsvetkov, V.G.; Sopin, V.P.; Tsvetkova, L.Ya.; Marchenko, G.N.,
Enthalpy of reaction of nitric acid with some organic compounds,
J. Gen. Chem. USSR, 1986, 56, 471-474. [all data]
Hendricks, de Clercq, et al., 2002
Hendricks, J.H.; de Clercq, H.L.; Freidhoff, C.B.; Arnold, S.T.; Eaton, J.G.; Fancher, C.; Lyapustina, S.A.; S.,
Anion solvation at the microscopic level: Photoelectron spectroscopy of the solvated anion clusters, NO-(Y)(n), where Y=Ar, Kr, Xe, N2O, H2S, NH3, H2O, and C2H4(OH)(2),
J. Chem. Phys., 2002, 116, 18, 7926-7938, https://doi.org/10.1063/1.1457444
. [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]
Holmes and Lossing, 1982
Holmes, J.L.; Lossing, F.P.,
Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part II. The effect of substitution at charge-bearing sites,
Can. J. Chem., 1982, 60, 2365. [all data]
Ohno, Imai, et al., 1985
Ohno, K.; Imai, K.; Harada, Y.,
Variations in reactivity of lone-pair electrons due to intramolecular hydrogen bonding as observed by penning ionization electron spectroscopy,
J. Am. Chem. Soc., 1985, 107, 8078. [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]
Von Niessen, Bieri, et al., 1980
Von Niessen, W.; Bieri, G.; Asbrink, L.,
30.4 nm He(II) photoelectron spectra of organic molecules. Part III. Oxo-compounds (C,H,O),
J. Electron Spectrosc. Relat. Phenom., 1980, 21, 175. [all data]
Holmes and Lossing, 1984
Holmes, J.L.; Lossing, F.P.,
Heats of formation of organic radicals from appearance energies,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 113. [all data]
Holmes, Lossing, et al., 1983
Holmes, J.L.; Lossing, F.P.; Terlouw, J.K.; Burgers, P.C.,
Novel gas-phase ions. The radical cations [CH2XH]+. (X = F, Cl, Br, I, OH, NH2, SH) and [CH2CH2NH3]+.,
Can. J. Chem., 1983, 61, 2305. [all data]
Holmes, Lossing, et al., 1982
Holmes, J.L.; Lossing, F.P.; Terlouw, J.K.; Burgers, P.C.,
The radical cation [CH2OH2]+ and related stable gas phase ion-dipole complexes,
J. Am. Chem. Soc., 1982, 104, 2931. [all data]
Burgers, Holmes, et al., 1987
Burgers, P.C.; Holmes, J.L.; Hop, C.E.C.A.; Postma, R.; Ruttink, P.J.A.; Terlouw, J.K.,
The isomeric [C2H6O2]+ hydrogen-bridged radical cations [CH2-O(H)...H...O=CH2]+, [CH3-O...H...O=CH2]+, and [CH3-O(H)...H...O=CH]+: Theory and experiment,
J. Am. Chem. Soc., 1987, 109, 7315. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas S°gas Entropy of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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