Acetic anhydride
- Formula: C4H6O3
- Molecular weight: 102.0886
- IUPAC Standard InChIKey: WFDIJRYMOXRFFG-UHFFFAOYSA-N
- 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Ion clustering 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 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
By formula: C4H6O3 + H2O = 2C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -13.53 ± 0.96 | kcal/mol | Cm | Becker and Maelicke, 1967 | liquid phase; ALS |
ΔrH° | -14.00 ± 0.09 | kcal/mol | Cm | Wadso, 1962 | liquid phase; ALS |
ΔrH° | -14.0 ± 0.1 | kcal/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydrolysis at 303 K; ALS |
By formula: C4H6O3 + C4H11N = C6H13NO + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -27.06 ± 0.11 | kcal/mol | Cm | Wadso, 1962 | liquid phase; ALS |
ΔrH° | -39.13 ± 0.06 | kcal/mol | Cm | Wadso, 1958 | liquid phase; Heat of aminolysis; ALS |
By formula: Na+ + C4H6O3 = (Na+ • C4H6O3)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
31.1 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
By formula: C4H6O3 + 2C3H6O3 = C6H10O5 + 2C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.0 | kcal/mol | Eqk | Utkin, Bogel'fer, et al., 1991 | liquid phase; NMR; ALS |
By formula: 2C2H4O2 = C4H6O3 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.22 ± 0.28 | kcal/mol | Eqk | Knopp, Linnell, et al., 1962 | liquid phase; ALS |
By formula: C4H6O3 + C6H7N = C8H9NO + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -24.11 ± 0.06 | kcal/mol | Cm | Wadso, 1962 | liquid phase; ALS |
By formula: C2H3NO4 + C2H4O2 = C4H6O3 + HNO3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 3.99 | kcal/mol | Cm | Tsvetkov, Shmakov, et al., 1989 | liquid phase; ALS |
By formula: C4H6O3 + C9H13N3O5 = C11H15N3O6 + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -10.5 | kcal/mol | Kin | Shatynski and Hanesian, 1993 | solid phase; ALS |
By formula: C2H2O + C2H4O2 = C4H6O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -20.9 ± 0.53 | kcal/mol | Eqk | Blake, Davies, et al., 1971 | gas phase; ALS |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, Ion clustering 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 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
IE (eV) | Method | Reference | Comment |
---|---|---|---|
~10.0 | PE | Bock, Hirabayashi, et al., 1981 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O+ | 10.14 | CH3COO | PI | Traeger, McLouglin, et al., 1982 | LBLHLM |
C2H3O+ | 10.19 ± 0.02 | ? | PI | Shigorin, Filyugina, et al., 1967 | RDSH |
C2H4O2+ | 9.65 ± 0.02 | CH2=CO? | PI | Shigorin, Filyugina, et al., 1967 | RDSH |
C3H3O3+ | 10.14 ± 0.02 | CH3 | PI | Shigorin, Filyugina, et al., 1967 | RDSH |
Ion clustering data
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: Robert C. Dunbar
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: Na+ + C4H6O3 = (Na+ • C4H6O3)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
31.1 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89 |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References
- 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.