Glyoxal

• Formula: C₂H₂O₂
• Molecular weight: 58.0361
• IUPAC Standard InChI: InChI=1S/C2H2O2/c3-1-2-4/h1-2H Copy

  
• IUPAC Standard InChIKey: LEQAOMBKQFMDFZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 107-22-2
• 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: Ethanedial; Biformal; Biformyl; Diformyl; Ethanedione; Glyoxal aldehyde; Glyoxylaldehyde; Oxal; Oxalaldehyde; 1,2-Ethanedione; (CHO)2; Diformal; Ethane-1,2-dione; Ethandial; Aerotex glyoxal 40; ODIX; Protectol GL 40
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Vibrational and/or electronic energy levels
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Mass spectrum (electron ionization)
• 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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 by: Robert L. Brown and Stephen E. Stein

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:
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

View reactions leading to C₂H₂O₂⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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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: Tanya L. Myers, Russell G. Tonkyn, Ashley M. Oeck, Tyler O. Danby, John S. Loring, Matthew S. Taubman, Stephen W. Sharpe, Jerome C. Birnbaum, and Timothy J. Johnson

Condensed Phase Spectrum

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Additional Data

Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   C_2h     Symmetry Number σ = 2

Source: Shimanouchi, 1972

Notes

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Fletcher and Pilcher, 1970
Fletcher, R.A.; Pilcher, G., Measurements of heats of combustion by flame calorimetry, Trans. Faraday Soc., 1970, 66, 794-799. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Compton D.A.C., 1977
Compton D.A.C., Values for the gas-phase thermodynamic functions of conjugated compounds existing as a mixture of conformers, J. Chem. Soc. Perkin Trans. 2, 1977, 1307-1311. [all data]

Hollenstein H., 1980
Hollenstein H., Sum of states, isomeric group and symmetry number of nonrigid molecules, Chem. Phys., 1980, 47, 269-285. [all data]

Natarajan A., 1982
Natarajan A., Vibrational analysis of glyoxal-h2, -d2 and -hd, J. Indian Chem. Soc., 1982, 59, 1156-1157. [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]

Compton, Reinhardt, et al., 1983
Compton, R.N.; Reinhardt, P.W.; Schweinler, H.C., Formation of gas-phase negative ions in vinylene carbonate, Int. J. Mass Spectrom. Ion Phys., 1983, 49, 113. [all data]

Buhl, Kramme, et al., 1991
Buhl, M.; Kramme, R.; Martin, H.; Mayer, B.; Nowack, G., Konformation und lichtabsorption von hexa-1,5-den-3,4-dion (divinylglyoxal), Chem. Ber., 1991, 124, 821. [all data]

Traeger, 1985
Traeger, J.C., Heat of formation for the formyl cation by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1985, 66, 271. [all data]

Reed and Brand, 1958
Reed, R.I.; Brand, J.C.D., Electron impact studies. Part 4. Glyoxal, methylglyoxal and diacetyl, J. Chem. Soc. Faraday Trans., 1958, 54, 478. [all data]

Verheijdt and Cerfontain, 1982
Verheijdt, P.L.; Cerfontain, H., Dipole moments, spectroscopy, and ground and excited state conformations of cycloalkane-1,2-diones, J. Chem. Soc. Perkin Trans. 2, 1982, 1541. [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]

Arnett, Newkome, et al., 1974
Arnett, J.F.; Newkome, G.; Mattice, W.L.; McGlynn, S.P., Excited electronic states of the α-dicarbonyls, J. Am. Chem. Soc., 1974, 96, 4385. [all data]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume II, J. Phys. Chem. Ref. Data, 1972, 6, 3, 993-1102. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  ΔcH°gas	Enthalpy of combustion of gas at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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