Acetic acid
- Formula: C2H4O2
- Molecular weight: 60.0520
- IUPAC Standard InChIKey: QTBSBXVTEAMEQO-UHFFFAOYSA-N
- CAS Registry Number: 64-19-7
- 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. - Isotopologues:
- Other names: Ethanoic acid; Ethylic acid; Glacial acetic acid; Methanecarboxylic acid; Vinegar acid; CH3COOH; Acetasol; Acide acetique; Acido acetico; Azijnzuur; Essigsaeure; Octowy kwas; Acetic acid, glacial; Kyselina octova; UN 2789; Aci-jel; Shotgun; Ethanoic acid monomer; NSC 132953
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- Information on this page:
- Other data available:
- Gas phase thermochemistry data
- Condensed phase thermochemistry data
- Phase change data
- Reaction thermochemistry data: reactions 51 to 79
- Henry's Law data
- Ion clustering data
- IR Spectrum
- Mass spectrum (electron ionization)
- UV/Visible spectrum
- Vibrational and/or electronic energy levels
- Gas Chromatography
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Reaction thermochemistry data
Go To: Top, 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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.
Reactions 1 to 50
By formula: F- + C2H4O2 = (F- • C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 185. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 107. | J/mol*K | N/A | Larson and McMahon, 1983 | gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 153. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B,M |
By formula: C2H5O+ + C2H4O2 = (C2H5O+ • C2H4O2)
Bond type: Hydrogen bonds of the type OH-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 118. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 123. | kJ/mol | ICR | Larson and McMahon, 1982 | gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 118. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 117. | J/mol*K | N/A | Larson and McMahon, 1982 | gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 88.7 | kJ/mol | ICR | Larson and McMahon, 1982 | gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M |
By formula: Cl- + C2H4O2 = (Cl- • C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 102.1 ± 0.84 | kJ/mol | TDAs | Sieck, 1985 | gas phase; B,M |
ΔrH° | 90.4 ± 8.4 | kJ/mol | TDAs | Yamdagni and Kebarle, 1971 | gas phase; B,M |
ΔrH° | 100. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 82.0 | J/mol*K | PHPMS | Sieck, 1985 | gas phase; M |
ΔrS° | 100. | J/mol*K | N/A | Larson and McMahon, 1984, 2 | gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
ΔrS° | 80.8 | J/mol*K | PHPMS | Yamdagni and Kebarle, 1971 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 77.8 ± 1.3 | kJ/mol | TDAs | Sieck, 1985 | gas phase; B |
ΔrG° | 66.1 ± 8.4 | kJ/mol | TDAs | Yamdagni and Kebarle, 1971 | gas phase; B |
ΔrG° | 69.9 ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
By formula: C2H3O2- + H+ = C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1457. ± 5.9 | kJ/mol | CIDC | Angel and Ervin, 2006 | gas phase; B |
ΔrH° | 1456. ± 9.2 | kJ/mol | G+TS | Taft and Topsom, 1987 | gas phase; B |
ΔrH° | 1459. ± 8.8 | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
ΔrH° | 1459. ± 9.2 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1435.9 ± 2.9 | kJ/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1427. ± 8.4 | kJ/mol | IMRE | Taft and Topsom, 1987 | gas phase; B |
ΔrG° | 1429. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
ΔrG° | 1430. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: C2H7O+ + C2H4O2 = (C2H7O+ • C2H4O2)
Bond type: Hydrogen bonds of the type OH-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 123. | kJ/mol | ICR | Larson and McMahon, 1982 | gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 119. | J/mol*K | N/A | Larson and McMahon, 1982 | gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 87.0 | kJ/mol | ICR | Larson and McMahon, 1982 | gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M |
By formula: CH6N+ + C2H4O2 = (CH6N+ • C2H4O2)
Bond type: Hydrogen bonds of the type NH+-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 92.0 | kJ/mol | PHPMS | Meot-Ner, 1984 | gas phase; M |
ΔrH° | 89.5 | kJ/mol | PHPMS | Meot-Ner, 1984 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 102. | J/mol*K | PHPMS | Meot-Ner, 1984 | gas phase; M |
ΔrS° | 100. | J/mol*K | N/A | Meot-Ner, 1984 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
43.1 | 459. | PHPMS | Meot-Ner, 1984 | gas phase; Entropy change calculated or estimated; M |
By formula: (C2H5O+ • 3C2H4O2) + C2H4O2 = (C2H5O+ • 4C2H4O2)
Bond type: Hydrogen bonds of the type OH-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 50. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | N/A | Meot-Ner (Mautner), 1992 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
26. | 245. | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; Entropy change calculated or estimated; M |
By formula: (C2H3O2- • 2C2H4O2 • H2O) + C2H4O2 = (C2H3O2- • 3C2H4O2 • H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.3 ± 2.5 | kJ/mol | N/A | Meot-ner, Elmore, et al., 1999 | gas phase; B |
ΔrH° | 67.8 ± 4.2 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 24.0 | kJ/mol | TDAs | Meot-ner, Elmore, et al., 1999 | gas phase; B |
ΔrG° | 26. ± 4.2 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
By formula: (C2H3O2- • C2H4O2 • H2O) + C2H4O2 = (C2H3O2- • 2C2H4O2 • H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 82.4 ± 2.1 | kJ/mol | N/A | Meot-ner, Elmore, et al., 1999 | gas phase; B |
ΔrH° | 67.8 ± 4.2 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 45.23 | kJ/mol | TDAs | Meot-ner, Elmore, et al., 1999 | gas phase; B |
ΔrG° | 26. ± 4.2 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
By formula: C2H3ClO + H2O = C2H4O2 + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -94.47 | kJ/mol | Cm | Devore and O'Neal, 1969 | liquid phase; Heat of hydrolysis; ALS |
ΔrH° | -92.30 | kJ/mol | Cm | Pritchard and Skinner, 1950 | liquid phase; Heat of hydrolysis at 298 K, see Carson and Skinner, 1949; ALS |
ΔrH° | -92.42 | kJ/mol | Cm | Carson and Skinner, 1949 | liquid phase; ALS |
By formula: C4H6O3 + H2O = 2C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -56.6 ± 4.0 | kJ/mol | Cm | Becker and Maelicke, 1967 | liquid phase; ALS |
ΔrH° | -58.6 ± 0.4 | kJ/mol | Cm | Wadso, 1962 | liquid phase; ALS |
ΔrH° | -58.4 ± 0.4 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydrolysis at 303 K; ALS |
By formula: I- + C2H4O2 = (I- • C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 70.7 ± 4.2 | kJ/mol | TDAs | Caldwell and Kebarle, 1984 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 89.1 | J/mol*K | PHPMS | Caldwell and Kebarle, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 43.9 ± 4.2 | kJ/mol | TDAs | Caldwell and Kebarle, 1984 | gas phase; B |
C2H3O2- + =
By formula: C2H3O2- + H+ = C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1540. ± 13. | kJ/mol | G+TS | Grabowski and Cheng, 1989 | gas phase; B |
ΔrH° | 1539. ± 19. | kJ/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1511. ± 13. | kJ/mol | IMRB | Grabowski and Cheng, 1989 | gas phase; B |
By formula: C6H5NO2- + C2H4O2 = (C6H5NO2- • C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 94.56 ± 0.42 | kJ/mol | TDAs | Sieck, 1985 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 112. | J/mol*K | PHPMS | Sieck, 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 61.09 ± 0.84 | kJ/mol | TDAs | Sieck, 1985 | gas phase; B |
By formula: C6H5O- + C2H4O2 = (C6H5O- • C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 115. | kJ/mol | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; calculated from CH3COO-.C6H5OH; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; calculated from CH3COO-.C6H5OH; M |
By formula: (C2H5O+ • 2C2H4O2) + C2H4O2 = (C2H5O+ • 3C2H4O2)
Bond type: Hydrogen bonds of the type OH-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 54.8 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 93.7 | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
By formula: (C2H5O+ • C2H4O2) + C2H4O2 = (C2H5O+ • 2C2H4O2)
Bond type: Hydrogen bonds of the type OH-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 77.4 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 103. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
By formula: C6H12NO3+ + C2H4O2 = (C6H12NO3+ • C2H4O2)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 75.7 | kJ/mol | PHPMS | Meot-Ner, 1984, 2 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 114. | J/mol*K | PHPMS | Meot-Ner, 1984, 2 | gas phase; M |
By formula: C4H7NO2 + H2O = C2H5NO + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -18.1 ± 0.2 | kJ/mol | Cm | Hill and Wadso, 1968 | solid phase; Heat of hydrolysis; ALS |
ΔrH° | -18.1 ± 0.2 | kJ/mol | Cm | Wadso, 1965 | solid phase; Heat of hydrolysis; ALS |
By formula: C4H10NO+ + C2H4O2 = (C4H10NO+ • C2H4O2)
Bond type: Hydrogen bonds of the type OH-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 77.0 | kJ/mol | PHPMS | Meot-Ner, 1984, 2 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 103. | J/mol*K | PHPMS | Meot-Ner, 1984, 2 | gas phase; M |
By formula: C2H3IO + H2O = HI + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -93.97 | kJ/mol | Cm | Devore and O'Neal, 1969 | liquid phase; Heat of hydrolysis; ALS |
ΔrH° | -90.33 | kJ/mol | Cm | Carson and Skinner, 1949 | liquid phase; Heat of hydrolysis; ALS |
By formula: (C2H3O2- • H2O) + C2H4O2 = (C2H3O2- • C2H4O2 • H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 123. ± 4.2 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 85.4 ± 6.7 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
By formula: C4H6O3 + C4H11N = C6H13NO + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -113.2 ± 0.46 | kJ/mol | Cm | Wadso, 1962 | liquid phase; ALS |
ΔrH° | -163.7 ± 0.3 | kJ/mol | Cm | Wadso, 1958 | liquid phase; Heat of aminolysis; ALS |
By formula: C2H3BrO + H2O = HBr + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -97.53 | kJ/mol | Cm | Devore and O'Neal, 1969 | liquid phase; Heat of hydrolysis; ALS |
ΔrH° | -96.48 | kJ/mol | Cm | Carson and Skinner, 1949 | liquid phase; ALS |
+
= C8H9O2S-
By formula: C6H5S- + C2H4O2 = C8H9O2S-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 84.94 ± 0.42 | kJ/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 52.3 ± 1.7 | kJ/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
By formula: (C2H3O2- • 2C2H4O2) + C2H4O2 = (C2H3O2- • 3C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 67.8 | kJ/mol | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 139. | J/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
By formula: (C2H3O2- • C2H4O2) + C2H4O2 = (C2H3O2- • 2C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 82.0 | kJ/mol | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
By formula: C6H5S- + C2H4O2 = (C6H5S- • C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 84.9 | kJ/mol | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | PHPMS | Sieck and Meot-ner, 1989 | gas phase; M |
By formula: Li+ + C2H4O2 = (Li+ • C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 174. | kJ/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 interpolated; M |
By formula: C2H3O2- + C2H4O2 = (C2H3O2- • C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 123. | kJ/mol | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 124. | J/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
By formula: C8H14O4 + 2H2O = C4H10O2 + 2C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -22.3 ± 2.1 | kJ/mol | Cm | Shlechter, Othmer, et al., 1945 | liquid phase; Heat of formation derived by Cox and Pilcher, 1970; ALS |
By formula: C5H6N2O + H2O = C3H4N2 + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -20.2 ± 0.2 | kJ/mol | Cm | Wadso, 1960 | liquid phase; solvent: Aqueous; Heat of hydrolysis; ALS |
By formula: C4H10O2 + 2C2H4O2 = C8H14O4 + 2H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 22.30 | kJ/mol | Eqk | Shlechter, Othmer, et al., 1945 | liquid phase; Heat of esterification at 338-453 K; ALS |
By formula: C6H12O3 + C2H4O2 = C8H14O4 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1.85 | kJ/mol | Eqk | Shlechter, Othmer, et al., 1945 | liquid phase; Heat of esterification at 338-453 K; ALS |
By formula: C6H9NO3 + 2H2O = C2H5NO + 2C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -103.5 ± 0.08 | kJ/mol | Cm | Hill and Wadso, 1968 | liquid phase; Heat of hydrolysis; ALS |
By formula: 2H2O + C4H8O2 = C2H4O2 + 2CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -74.4 ± 3.6 | kJ/mol | Cm | Guthrie and Liu, 1995 | liquid phase; Heat of hydrolysis; ALS |
By formula: C10H14 + C2H4O2 = C12H18O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -182.0 ± 0.3 | kJ/mol | Cac | Wiberg, Connon, et al., 1979 | liquid phase; solvent: Acetic acid; ALS |
By formula: C2H4OS + H2O = C2H4O2 + H2S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -2.7 ± 0.3 | kJ/mol | Cm | Sunner and Wadso, 1957 | liquid phase; Heat of hydrolysis; ALS |
By formula: C2H5NO + H2O = C2H4O2 + H3N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 76.1 ± 1.4 | kJ/mol | Cm | Hill and Wadso, 1968 | solid phase; Heat of hydrolysis; ALS |
By formula: C6H13NO + C2H4O2 = C8H15NO2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 40.5 ± 0.50 | kJ/mol | Cm | Wadso, 1965 | liquid phase; Heat of hydrolysis; ALS |
By formula: C5H10OS + H2O = C3H8S + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -3.9 ± 0.3 | kJ/mol | Cm | Wadso, 1957 | liquid phase; Heat of hydrolysis; ALS |
+
= C10H11NO2 +
By formula: C8H9NO + C2H4O2 = C10H11NO2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 45.5 ± 0.3 | kJ/mol | Cm | Wadso, 1965 | solid phase; Heat of hydrolysis; ALS |
By formula: C9H10O2 + H2O = C7H8O + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -18.4 ± 0.59 | kJ/mol | Cm | Sunner, 1957 | liquid phase; Heat of hydrolysis; ALS |
By formula: H2O + C6H12OS = C4H10S + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.6 ± 0.3 | kJ/mol | Cm | Wadso, 1957 | liquid phase; Heat of hydrolysis; ALS |
By formula: C3H4N4O + H2O = CH2N4 + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -43.1 ± 0.4 | kJ/mol | Cm | Wadso, 1960 | solid phase; Heat of hydrolysis; ALS |
By formula: C9H8O3S + H2O = C7H6O2S + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -11.5 ± 0.4 | kJ/mol | Cm | Nelander, 1964 | solid phase; Heat of hydrolysis; ALS |
By formula: C8H9NO + H2O = C6H7N + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -42.0 ± 0.3 | kJ/mol | Cm | Wadso, 1965 | solid phase; Heat of hydrolysis; ALS |
By formula: C2H4O2 + C3H6O = C5H8O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 60.2 ± 0.3 | kJ/mol | Cm | Sunner, 1957 | liquid phase; Heat of hydrolysis; ALS |
By formula: C4H8OS + H2O = C2H4O2 + C2H6S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.0 ± 0.3 | kJ/mol | Cm | Wadso, 1957 | liquid phase; Heat of hydrolysis; ALS |
By formula: H2O + C5H10OS = C2H4O2 + C3H8S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -5.8 ± 0.3 | kJ/mol | Cm | Wadso, 1957 | liquid phase; Heat of hydrolysis; ALS |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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
L - 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman
View reactions leading to C2H4O2+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 10.65 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 783.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 752.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.63 | PI | Traeger, McLouglin, et al., 1982 | LBLHLM |
10.66 | EI | Holmes, Fingas, et al., 1981 | LLK |
10.66 ± 0.05 | EI | Holmes and Lossing, 1980 | LLK |
10.66 | EI | Holmes and Lossing, 1980, 2 | LLK |
10.66 ± 0.05 | PI | Akopyan and Villem, 1976 | LLK |
10.664 ± 0.003 | PI | Watanabe, Yokoyama, et al., 1974 | LLK |
10.644 ± 0.002 | PI | Knowles and Nicholson, 1974 | LLK |
10.65 | PE | Watanabe, Yokoyama, et al., 1973 | LLK |
10.69 ± 0.03 | PE | Thomas, 1972 | LLK |
10.70 | PE | Sweigart and Turner, 1972 | LLK |
10.37 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
10.38 ± 0.03 | PI | Vilesov, 1960 | RDSH |
10.35 ± 0.03 | PI | Watanabe, 1957 | RDSH |
10.9 | PE | Von Niessen, Bieri, et al., 1980 | Vertical value; LLK |
10.84 | PE | Carnovale, Gan, et al., 1980 | Vertical value; LLK |
10.63 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
11.5 | PE | Rao, 1975 | Vertical value; LLK |
10.87 | PE | Kimura, Katsumata, et al., 1975 | Vertical value; LLK |
10.8 | PE | Green and Hayes, 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C+ | 22.0 ± 0.5 | H2+HCOOH | EI | Stepanov, Perov, et al., 1988 | LL |
CHO2+ | 12.27 ± 0.05 | CH3 | EI | Haney and Franklin, 1969 | RDSH |
CHO2+ | 12.9 ± 0.1 | CH3 | EI | Shigorin, Filyugina, et al., 1966 | RDSH |
CH3+ | 14.0 ± 0.15 | ? | EI | Haney and Franklin, 1969 | RDSH |
CH3O+ | 12.05 ± 0.10 | CHO | EI | Selim and Helal, 1981 | LLK |
CO+ | 15.3 ± 0.1 | CH3OH | EI | Shigorin, Filyugina, et al., 1966 | RDSH |
C2H3O+ | 11.54 | OH | PI | Traeger, McLouglin, et al., 1982 | LBLHLM |
C2H3O+ | 11.75 | OH | EI | Haney and Franklin, 1969 | RDSH |
C2H3O+ | 11.4 ± 0.15 | OH | EI | Shigorin, Filyugina, et al., 1966 | RDSH |
OH+ | 15.1 | ? | EI | Majer, Patrick, et al., 1961 | RDSH |
De-protonation reactions
By formula: C2H3O2- + H+ = C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1457. ± 5.9 | kJ/mol | CIDC | Angel and Ervin, 2006 | gas phase; B |
ΔrH° | 1456. ± 9.2 | kJ/mol | G+TS | Taft and Topsom, 1987 | gas phase; B |
ΔrH° | 1459. ± 8.8 | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
ΔrH° | 1459. ± 9.2 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1435.9 ± 2.9 | kJ/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1427. ± 8.4 | kJ/mol | IMRE | Taft and Topsom, 1987 | gas phase; B |
ΔrG° | 1429. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
ΔrG° | 1430. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
C2H3O2- + =
By formula: C2H3O2- + H+ = C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1540. ± 13. | kJ/mol | G+TS | Grabowski and Cheng, 1989 | gas phase; B |
ΔrH° | 1539. ± 19. | kJ/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1511. ± 13. | kJ/mol | IMRB | Grabowski and Cheng, 1989 | gas phase; B |
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.
Larson and McMahon, 1983
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Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding,
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Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria,
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Cumming and Kebarle, 1978
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Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
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Meot-Ner, 1984
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The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects,
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Ionic Hydrogen Bond Effects on the Acidities, Basicities, Solvation, Solvent Bridging and Self-assembly of Carboxylic Groups,
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The ionic hydrogen bond and ion solvation. 5. OH...O- bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions,
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Devore and O'Neal, 1969
Devore, J.A.; O'Neal, H.E.,
Heats of formation of the acetyl halides and of the acetyl radical,
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Pritchard and Skinner, 1950
Pritchard, H.O.; Skinner, H.A.,
The heats of hydrolysis of the chloro-substituted acetyl chlorides,
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Carson and Skinner, 1949
Carson, A.S.; Skinner, H.A.,
201. Carbon-halogen bond energies in the acetyl halides,
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Becker and Maelicke, 1967
Becker, F.; Maelicke, A.,
Thermokinetische Messungen nach dem Prinzip der Wärmefluβkalorimetrie,
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Wadso, 1962
Wadso, I.,
Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride,
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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,
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Caldwell and Kebarle, 1984
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Binding energies and structural effects in halide anion-ROH and -RCOOH complexes from gas phase equilibria measurements,
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Grabowski and Cheng, 1989
Grabowski, J.J.; Cheng, X.,
Gas-Phase Formation of the Enolate Monoanion of Acetic Acid by Proton Abstraction,
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Meot-Ner, 1984, 2
Meot-Ner, (Mautner),
The Ionic Hydrogen Bond. 4. Intramolecular and Multiple Bonds. Proton Affinities, Hydration and Complexes of Amides and Amino Acid Derivatives,
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Hill and Wadso, 1968
Hill, J.O.; Wadso, I.,
Some thermochemical properties of N,N,N-triacetylammonia,
Acta Chem. Scand., 1968, 22, 1590-1594. [all data]
Wadso, 1965
Wadso, I.,
Thermochemical properties of diacetimide, N-butyldiacetimide and N-phenyldiacetimide,
Acta Chem. Scand., 1965, 19, 1079-1087. [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]
Sieck and Meot-ner, 1989
Sieck, L.W.; Meot-ner, M.,
Ionic Hydrogen Bond and Ion Solvation. 8. RS-..HOR Bond Strengths. Correlation with Acidities.,
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Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L.,
Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases,
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Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P.,
Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n,
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. [all data]
Shlechter, Othmer, et al., 1945
Shlechter, N.; Othmer, D.F.; Marshak, S.,
Esterification of 2,3-butylene glycol with acetic acid,
Ind. Eng. Chem., 1945, 37, 900-905. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Wadso, 1960
Wadso, I.,
Heats of hydrolysis of N-acetylated imidazole, 1,2,4-triazole and tetrazole,
Acta Chem. Scand., 1960, 14, 903-908. [all data]
Guthrie and Liu, 1995
Guthrie, J.P.; Liu, Z.,
The enols of acetic acid and methyl acetate,
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Wiberg, Connon, et al., 1979
Wiberg, K.B.; Connon, H.A.; Pratt, W.E.,
Enthalpies of acetolysis of tricyclo[3.2.1.01,5]octane ([3.2.1]propellane) and 1,3-dehydroadamantane,
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Sunner and Wadso, 1957
Sunner, S.; Wadso, I.,
The heat of hydrolysis of thiolacetic acid,
Trans. Faraday Soc., 1957, 53, 455-459. [all data]
Wadso, 1957
Wadso, I.,
The heats of hydrolysis of some alkyl thiolesters,
Acta Chem. Scand., 1957, 11, 1745-1751. [all data]
Sunner, 1957
Sunner, S.,
The heat of hydrolysis of i-propenyl acetate and m-cresyl acetate and the heat of formation of acetone,
Acta Chem. Scand., 1957, 11, 1757-1760. [all data]
Nelander, 1964
Nelander, L.,
The heats of hydrolysis of aspirin, thioaspirin, and their p-analogues,
Acta Chem. Scand., 1964, 18, 973-984. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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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]
Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P.,
Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations,
Can. J. Chem., 1981, 59, 80. [all data]
Holmes and Lossing, 1980
Holmes, J.L.; Lossing, F.P.,
Thermochemistry and unimolecular reactions of ionized acetic acid and its enol in the gas phase.,
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Holmes and Lossing, 1980, 2
Holmes, J.L.; Lossing, F.P.,
Gas-phase heats of formation of keto and enol ions of carbonyl compounds.,
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Akopyan and Villem, 1976
Akopyan, M.E.; Villem, Ya.Ya.,
Ion-molecule reactions in the photoionization of formic and acetic acid vapors,
High Energy Chem., 1976, 10, 24. [all data]
Watanabe, Yokoyama, et al., 1974
Watanabe, I.; Yokoyama, Y.; Ikeda, S.,
Vibrational structures in the He(I) photoelectron spectra of carboxylic acids,
Bull. Chem. Soc. Jpn., 1974, 47, 627. [all data]
Knowles and Nicholson, 1974
Knowles, D.J.; Nicholson, A.J.C.,
Ionization energies of formic and acetic acid monomers,
J. Chem. Phys., 1974, 60, 1180. [all data]
Watanabe, Yokoyama, et al., 1973
Watanabe, I.; Yokoyama, Y.; Ikeda, S.,
Lone pair ionization potentials of carboxylic acids determined by He(I) photoelectron spectroscopy,
Bull. Chem. Soc. Jpn., 1973, 46, 1959. [all data]
Thomas, 1972
Thomas, R.K.,
Photoelectron spectroscopy of hydrogen-bonded systems: spectra of monomers, dimers and mixed complexes of carboxylic acides,
Proc. R. Soc. London A:, 1972, 331, 249. [all data]
Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W.,
Lone pair orbitals and their interactions studied by photoelectron spectroscopy. I. Carboxylic acids and their derivatives,
J. Am. Chem. Soc., 1972, 94, 5592. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
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Vilesov, 1960
Vilesov, F.I.,
The photoionization of vapors of compounds whose molecules contain carbonyl groups,
Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [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]
Carnovale, Gan, et al., 1980
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Photoelectron spectroscopic studies of the monomers and dimers of acetic and trifluoracetic acids,
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Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G.,
Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules,
J. Am. Chem. Soc., 1977, 99, 3980. [all data]
Rao, 1975
Rao, C.N.R.,
Lone-pair ionization bands of chromophores in the photoelectron spectra of organic molecules,
Indian J. Chem., 1975, 13, 950. [all data]
Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Yamazaki, T.; Wakabayashi, H.,
UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure,
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Green and Hayes, 1975
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Ionization energies of an Mo-Mo quadruple bond; a He(I) photoelectron study of some molybdenum-dycarboxylate dimers,
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Stepanov, Perov, et al., 1988
Stepanov, A.N.; Perov, A.A.; Kabanov, S.P.; Simonov, A.P.,
Formation of long-lived, highly excited atoms during dissociative excitation of CH3CN, CH3CH2OH, CH3COOH, HCOOH, and C4H4S molecules on electron impact,
Russ. J. Phys. Chem., 1988, 22, 81. [all data]
Haney and Franklin, 1969
Haney, M.A.; Franklin, J.L.,
Excess energies in mass spectra of some oxygen-containing organic compounds,
J. Chem. Soc. Faraday Trans., 1969, 65, 1794. [all data]
Shigorin, Filyugina, et al., 1966
Shigorin, D.N.; Filyugina, A.D.; Potapov, V.K.,
Ionization and dissociation of molecules of acetaldehyde, acetone, and acetic acid on electron impact,
Teor. i Eksperim. Khim., 1966, 2, 554, In original 417. [all data]
Selim and Helal, 1981
Selim, E.T.M.; Helal, A.I.,
Heat of formation of CH2=OH+ fragment ion,
Indian J. Pure Appl. Phys., 1981, 19, 977. [all data]
Majer, Patrick, et al., 1961
Majer, J.R.; Patrick, C.R.; Robb, J.C.,
Appearance potentials of the acetyl radical-ion,
J. Chem. Soc. Faraday Trans., 1961, 57, 14. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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