1,2-Ethanediol

• Formula: C₂H₆O₂
• Molecular weight: 62.0678
• IUPAC Standard InChI: InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2 Copy

  
• IUPAC Standard InChIKey: LYCAIKOWRPUZTN-UHFFFAOYSA-N Copy
• 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:
  • Pluronic f-68
• 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
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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:
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

( • ) +  = ( • 2)

By formula: (Cl^- • C₂H₆O₂) + C₂H₆O₂ = (Cl^- • 2C₂H₆O₂)

 +  = ( • )

By formula: Cl^- + C₂H₆O₂ = (Cl^- • C₂H₆O₂)

C₂H₅O₂^- +  =

By formula: C₂H₅O₂^- + H⁺ = C₂H₆O₂

 +  =  + 

By formula: C₂H₆O₂ + C₃H₆O = C₅H₁₀O₂ + H₂O

 +  =  + 

By formula: C₂H₆O₂ + HNO₃ = C₂H₅NO₄ + H₂O

 +  = C₂H₆NO₃^-

By formula: NO^- + C₂H₆O₂ = C₂H₆NO₃^-

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:
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)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₂H₅O₂^- +  =

By formula: C₂H₅O₂^- + H⁺ = C₂H₆O₂

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: John E. Bartmess

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: Cl^- + C₂H₆O₂ = (Cl^- • C₂H₆O₂)

( • ) +  = ( • 2)

By formula: (Cl^- • C₂H₆O₂) + C₂H₆O₂ = (Cl^- • 2C₂H₆O₂)

 +  = C₂H₆NO₃^-

By formula: NO^- + C₂H₆O₂ = C₂H₆NO₃^-

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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.

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]

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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]

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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]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

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Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

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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]

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Poskrobko, J.; Linkiewicz, M.; Jaworski, M., Analysis of high-boiling ethoxylates of methyl, ethyl and butyl alcohols, with the use of gas chromatography, Chem. Anal. (Warsaw), 1994, 39, 2, 153-159. [all data]

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Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y., Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion, J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037 . [all data]

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Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y., Off-flavor compounds in spray-dried skim milk powder, J. Agric. Food Chem., 1994, 42, 6, 1323-1327, https://doi.org/10.1021/jf00042a014 . [all data]

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Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y., Volatile flavor compounds in spray-dried skim milk powder, J. Agric. Food Chem., 1994, 42, 4, 984-988, https://doi.org/10.1021/jf00040a028 . [all data]

Leffingwell and Alford, 2011
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Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

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Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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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