Acetic anhydride

• Formula: C₄H₆O₃
• Molecular weight: 102.0886
• IUPAC Standard InChI: InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3 Copy

  
• IUPAC Standard InChIKey: WFDIJRYMOXRFFG-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-24-7
• 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: Acetic acid, anhydride; Acetic oxide; Acetyl anhydride; Acetyl ether; Acetyl oxide; Ethanoic anhydride; (CH3CO)2O; Ethanoic anhydrate; Acetanhydride; Anhydride acetique; Anhydrid kyseliny octove; Anidride acetica; Azijnzuuranhydride; Essigsaeureanhydrid; Octowy bezwodnik; UN 1715; Acetyl acetate; Acetic acid, 1,1'-anhydride
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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  • Gas Phase Kinetics Database
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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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: C₄H₆O₃ + H₂O = 2C₂H₄O₂

 +  =  + 

By formula: C₄H₆O₃ + C₄H₁₁N = C₆H₁₃NO + C₂H₄O₂

 +  = ( • )

By formula: Na⁺ + C₄H₆O₃ = (Na⁺ • C₄H₆O₃)

Free energy of reaction

 + 2 =  + 2

By formula: C₄H₆O₃ + 2C₃H₆O₃ = C₆H₁₀O₅ + 2C₂H₄O₂

2 =  + 

By formula: 2C₂H₄O₂ = C₄H₆O₃ + H₂O

 +  =  + 

By formula: C₄H₆O₃ + C₆H₇N = C₈H₉NO + C₂H₄O₂

 +  =  + 

By formula: C₂H₃NO₄ + C₂H₄O₂ = C₄H₆O₃ + HNO₃

 +  =  + 

By formula: C₄H₆O₃ + C₉H₁₃N₃O₅ = C₁₁H₁₅N₃O₆ + C₂H₄O₂

 +  =

By formula: C₂H₂O + C₂H₄O₂ = C₄H₆O₃

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 compiled as indicated in comments:
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₄H₆O₃⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

Becker and Maelicke, 1967
Becker, F.; Maelicke, A., Thermokinetische Messungen nach dem Prinzip der Wärmefluβkalorimetrie, Z. Phys. Chem. (Neue Folge), 1967, 55, 280-295. [all data]

Wadso, 1962
Wadso, I., Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride, Acta Chem. Scand., 1962, 16, 471-478. [all data]

Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A., Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides, J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]

Wadso, 1958
Wadso, I., The heats of aminolysis of n-butyl thiolacetate and acetic anhydride, Acta Chem. Scand., 1958, 12, 635-640. [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Utkin, Bogel'fer, et al., 1991
Utkin, A.Yu.; Bogel'fer, L.Ya.; Chimishkyan, A.L., Reversible reactions in the acidolysis of methyoxyacetic acid by acetic anhydride, Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 1049-1059, In original 1974. [all data]

Knopp, Linnell, et al., 1962
Knopp, J.A.; Linnell, W.S.; Child, W.C., Jr., The thermodynamics of the thermal decomposition of acetic acid in the liquid phase, J. Phys. Chem., 1962, 66, 1513-1516. [all data]

Tsvetkov, Shmakov, et al., 1989
Tsvetkov, V.G.; Shmakov, V.A.; Sopin, V.F.; Ivanov, A.V.; Ikonnikov, A.A.; Marchenko, G.N., Enthalpies of reaction of nitric acid with acetic and trifluoroacetic anhydrides, J. Gen. Chem. USSR, 1989, 59, 1220-1222. [all data]

Shatynski and Hanesian, 1993
Shatynski, J.J.; Hanesian, D., Adiabatic kinetic studies of the cytidine/acetic anhydride reaction by utilizing temperature versus time data, Ind. Eng. Chem. Res., 1993, 32, 594-599. [all data]

Blake, Davies, et al., 1971
Blake, P.G.; Davies, H.H.; Speis, A., Reactions of keten. Part II. The thermodynamics of the gas-phase equilibrium: acetic acid + keten = acetic anhydride, J. Chem. Soc. B, 1971, 2050-2052. [all data]

Bock, Hirabayashi, et al., 1981
Bock, H.; Hirabayashi, T.; Mohmand, S., Thermische erzeugung von alkyl- und halogenketenen, Chem. Ber., 1981, 114, 2595. [all data]

Traeger, McLouglin, et al., 1982
Traeger, J.C.; McLouglin, R.G.; Nicholson, A.J.C., Heat of formation for acetyl cation in the gas phase, J. Am. Chem. Soc., 1982, 104, 5318. [all data]

Shigorin, Filyugina, et al., 1967
Shigorin, D.N.; Filyugina, A.D.; Potapov, V.K., Role of intramolecular hydrogen bonding in the ionisation and dissociation of compounds, Zh. Fiz. Khim., 1967, 41, 2336, In original 1255. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  T	Temperature
  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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