Acetic acid

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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

Fluorine anion + Acetic acid = (Fluorine anion • Acetic acid)

By formula: F- + C2H4O2 = (F- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr185. ± 8.4kJ/molIMRELarson and McMahon, 1983gas 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
Δr107.J/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Δr153. ± 8.4kJ/molIMRELarson and McMahon, 1983gas 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

C2H5O+ + Acetic acid = (C2H5O+ • Acetic acid)

By formula: C2H5O+ + C2H4O2 = (C2H5O+ • C2H4O2)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Δr118.kJ/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Δr123.kJ/molICRLarson and McMahon, 1982gas 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
Δr118.J/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M
Δr117.J/mol*KN/ALarson and McMahon, 1982gas 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
Δr88.7kJ/molICRLarson and McMahon, 1982gas 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

Chlorine anion + Acetic acid = (Chlorine anion • Acetic acid)

By formula: Cl- + C2H4O2 = (Cl- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr102.1 ± 0.84kJ/molTDAsSieck, 1985gas phase; B,M
Δr90.4 ± 8.4kJ/molTDAsYamdagni and Kebarle, 1971gas phase; B,M
Δr100. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Δr82.0J/mol*KPHPMSSieck, 1985gas phase; M
Δr100.J/mol*KN/ALarson and McMahon, 1984, 2gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Δr80.8J/mol*KPHPMSYamdagni and Kebarle, 1971gas phase; M
Quantity Value Units Method Reference Comment
Δr77.8 ± 1.3kJ/molTDAsSieck, 1985gas phase; B
Δr66.1 ± 8.4kJ/molTDAsYamdagni and Kebarle, 1971gas phase; B
Δr69.9 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

MeCO2 anion + Hydrogen cation = Acetic acid

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Δr1457. ± 5.9kJ/molCIDCAngel and Ervin, 2006gas phase; B
Δr1456. ± 9.2kJ/molG+TSTaft and Topsom, 1987gas phase; B
Δr1459. ± 8.8kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Δr1459. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1435.9 ± 2.9kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Δr1427. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; B
Δr1429. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B
Δr1430. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

C2H7O+ + Acetic acid = (C2H7O+ • Acetic acid)

By formula: C2H7O+ + C2H4O2 = (C2H7O+ • C2H4O2)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Δr123.kJ/molICRLarson and McMahon, 1982gas 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
Δr119.J/mol*KN/ALarson and McMahon, 1982gas 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
Δr87.0kJ/molICRLarson and McMahon, 1982gas 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

CH6N+ + Acetic acid = (CH6N+ • Acetic acid)

By formula: CH6N+ + C2H4O2 = (CH6N+ • C2H4O2)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Δr92.0kJ/molPHPMSMeot-Ner, 1984gas phase; M
Δr89.5kJ/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr102.J/mol*KPHPMSMeot-Ner, 1984gas phase; M
Δr100.J/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
43.1459.PHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

(C2H5O+ • 3Acetic acid) + Acetic acid = (C2H5O+ • 4Acetic acid)

By formula: (C2H5O+ • 3C2H4O2) + C2H4O2 = (C2H5O+ • 4C2H4O2)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Δr50.kJ/molPHPMSMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KN/AMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
26.245.PHPMSMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated; M

(MeCO2 anion • 2Acetic acid • Water) + Acetic acid = (MeCO2 anion • 3Acetic acid • Water)

By formula: (C2H3O2- • 2C2H4O2 • H2O) + C2H4O2 = (C2H3O2- • 3C2H4O2 • H2O)

Quantity Value Units Method Reference Comment
Δr52.3 ± 2.5kJ/molN/AMeot-ner, Elmore, et al., 1999gas phase; B
Δr67.8 ± 4.2kJ/molTDAsMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Δr24.0kJ/molTDAsMeot-ner, Elmore, et al., 1999gas phase; B
Δr26. ± 4.2kJ/molTDAsMeot-Ner and Sieck, 1986gas phase; B

(MeCO2 anion • Acetic acid • Water) + Acetic acid = (MeCO2 anion • 2Acetic acid • Water)

By formula: (C2H3O2- • C2H4O2 • H2O) + C2H4O2 = (C2H3O2- • 2C2H4O2 • H2O)

Quantity Value Units Method Reference Comment
Δr82.4 ± 2.1kJ/molN/AMeot-ner, Elmore, et al., 1999gas phase; B
Δr67.8 ± 4.2kJ/molTDAsMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Δr45.23kJ/molTDAsMeot-ner, Elmore, et al., 1999gas phase; B
Δr26. ± 4.2kJ/molTDAsMeot-Ner and Sieck, 1986gas phase; B

Acetyl chloride + Water = Acetic acid + Hydrogen chloride

By formula: C2H3ClO + H2O = C2H4O2 + HCl

Quantity Value Units Method Reference Comment
Δr-94.47kJ/molCmDevore and O'Neal, 1969liquid phase; Heat of hydrolysis; ALS
Δr-92.30kJ/molCmPritchard and Skinner, 1950liquid phase; Heat of hydrolysis at 298 K, see Carson and Skinner, 1949; ALS
Δr-92.42kJ/molCmCarson and Skinner, 1949liquid phase; ALS

Acetic anhydride + Water = 2Acetic acid

By formula: C4H6O3 + H2O = 2C2H4O2

Quantity Value Units Method Reference Comment
Δr-56.6 ± 4.0kJ/molCmBecker and Maelicke, 1967liquid phase; ALS
Δr-58.6 ± 0.4kJ/molCmWadso, 1962liquid phase; ALS
Δr-58.4 ± 0.4kJ/molCmConn, Kistiakowsky, et al., 1942liquid phase; Heat of hydrolysis at 303 K; ALS

Iodide + Acetic acid = (Iodide • Acetic acid)

By formula: I- + C2H4O2 = (I- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr70.7 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Δr89.1J/mol*KPHPMSCaldwell and Kebarle, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr43.9 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B

C2H3O2- + Hydrogen cation = Acetic acid

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Δr1540. ± 13.kJ/molG+TSGrabowski and Cheng, 1989gas phase; B
Δr1539. ± 19.kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Δr1511. ± 13.kJ/molIMRBGrabowski and Cheng, 1989gas phase; B

C6H5NO2- + Acetic acid = (C6H5NO2- • Acetic acid)

By formula: C6H5NO2- + C2H4O2 = (C6H5NO2- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr94.56 ± 0.42kJ/molTDAsSieck, 1985gas phase; B,M
Quantity Value Units Method Reference Comment
Δr112.J/mol*KPHPMSSieck, 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr61.09 ± 0.84kJ/molTDAsSieck, 1985gas phase; B

phenoxide anion + Acetic acid = (phenoxide anion • Acetic acid)

By formula: C6H5O- + C2H4O2 = (C6H5O- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr115.kJ/molPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M

(C2H5O+ • 2Acetic acid) + Acetic acid = (C2H5O+ • 3Acetic acid)

By formula: (C2H5O+ • 2C2H4O2) + C2H4O2 = (C2H5O+ • 3C2H4O2)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Δr54.8kJ/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
Δr93.7J/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M

(C2H5O+ • Acetic acid) + Acetic acid = (C2H5O+ • 2Acetic acid)

By formula: (C2H5O+ • C2H4O2) + C2H4O2 = (C2H5O+ • 2C2H4O2)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Δr77.4kJ/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
Δr103.J/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M

C6H12NO3+ + Acetic acid = (C6H12NO3+ • Acetic acid)

By formula: C6H12NO3+ + C2H4O2 = (C6H12NO3+ • C2H4O2)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr75.7kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr114.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

Diacetamide + Water = Acetamide + Acetic acid

By formula: C4H7NO2 + H2O = C2H5NO + C2H4O2

Quantity Value Units Method Reference Comment
Δr-18.1 ± 0.2kJ/molCmHill and Wadso, 1968solid phase; Heat of hydrolysis; ALS
Δr-18.1 ± 0.2kJ/molCmWadso, 1965solid phase; Heat of hydrolysis; ALS

C4H10NO+ + Acetic acid = (C4H10NO+ • Acetic acid)

By formula: C4H10NO+ + C2H4O2 = (C4H10NO+ • C2H4O2)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Δr77.0kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr103.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

Acetyl iodide + Water = Hydrogen iodide + Acetic acid

By formula: C2H3IO + H2O = HI + C2H4O2

Quantity Value Units Method Reference Comment
Δr-93.97kJ/molCmDevore and O'Neal, 1969liquid phase; Heat of hydrolysis; ALS
Δr-90.33kJ/molCmCarson and Skinner, 1949liquid phase; Heat of hydrolysis; ALS

(MeCO2 anion • Water) + Acetic acid = (MeCO2 anion • Acetic acid • Water)

By formula: (C2H3O2- • H2O) + C2H4O2 = (C2H3O2- • C2H4O2 • H2O)

Quantity Value Units Method Reference Comment
Δr123. ± 4.2kJ/molTDAsMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Δr85.4 ± 6.7kJ/molTDAsMeot-Ner and Sieck, 1986gas phase; B

Acetic anhydride + 1-Butanamine = Acetamide, N-butyl- + Acetic acid

By formula: C4H6O3 + C4H11N = C6H13NO + C2H4O2

Quantity Value Units Method Reference Comment
Δr-113.2 ± 0.46kJ/molCmWadso, 1962liquid phase; ALS
Δr-163.7 ± 0.3kJ/molCmWadso, 1958liquid phase; Heat of aminolysis; ALS

Acetyl bromide + Water = Hydrogen bromide + Acetic acid

By formula: C2H3BrO + H2O = HBr + C2H4O2

Quantity Value Units Method Reference Comment
Δr-97.53kJ/molCmDevore and O'Neal, 1969liquid phase; Heat of hydrolysis; ALS
Δr-96.48kJ/molCmCarson and Skinner, 1949liquid phase; ALS

thiophenoxide anion + Acetic acid = C8H9O2S-

By formula: C6H5S- + C2H4O2 = C8H9O2S-

Quantity Value Units Method Reference Comment
Δr84.94 ± 0.42kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr52.3 ± 1.7kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

(MeCO2 anion • 2Acetic acid) + Acetic acid = (MeCO2 anion • 3Acetic acid)

By formula: (C2H3O2- • 2C2H4O2) + C2H4O2 = (C2H3O2- • 3C2H4O2)

Quantity Value Units Method Reference Comment
Δr67.8kJ/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr139.J/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

(MeCO2 anion • Acetic acid) + Acetic acid = (MeCO2 anion • 2Acetic acid)

By formula: (C2H3O2- • C2H4O2) + C2H4O2 = (C2H3O2- • 2C2H4O2)

Quantity Value Units Method Reference Comment
Δr82.0kJ/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr120.J/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

thiophenoxide anion + Acetic acid = (thiophenoxide anion • Acetic acid)

By formula: C6H5S- + C2H4O2 = (C6H5S- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr84.9kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

Lithium ion (1+) + Acetic acid = (Lithium ion (1+) • Acetic acid)

By formula: Li+ + C2H4O2 = (Li+ • C2H4O2)

Quantity Value Units Method Reference Comment
Δr174.kJ/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 interpolated; M

MeCO2 anion + Acetic acid = (MeCO2 anion • Acetic acid)

By formula: C2H3O2- + C2H4O2 = (C2H3O2- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr123.kJ/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr124.J/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

2,3-Butanediol, diacetate + 2Water = 2,3-Butanediol + 2Acetic acid

By formula: C8H14O4 + 2H2O = C4H10O2 + 2C2H4O2

Quantity Value Units Method Reference Comment
Δr-22.3 ± 2.1kJ/molCmShlechter, Othmer, et al., 1945liquid phase; Heat of formation derived by Cox and Pilcher, 1970; ALS

1H-Imidazole, 1-acetyl- + Water = 1H-Imidazole + Acetic acid

By formula: C5H6N2O + H2O = C3H4N2 + C2H4O2

Quantity Value Units Method Reference Comment
Δr-20.2 ± 0.2kJ/molCmWadso, 1960liquid phase; solvent: Aqueous; Heat of hydrolysis; ALS

2,3-Butanediol + 2Acetic acid = 2,3-Butanediol, diacetate + 2Water

By formula: C4H10O2 + 2C2H4O2 = C8H14O4 + 2H2O

Quantity Value Units Method Reference Comment
Δr22.30kJ/molEqkShlechter, Othmer, et al., 1945liquid phase; Heat of esterification at 338-453 K; ALS

2,3-Butanediol monoacetate + Acetic acid = 2,3-Butanediol, diacetate + Water

By formula: C6H12O3 + C2H4O2 = C8H14O4 + H2O

Quantity Value Units Method Reference Comment
Δr1.85kJ/molEqkShlechter, Othmer, et al., 1945liquid phase; Heat of esterification at 338-453 K; ALS

N,N,N-Triacetylamine + 2Water = Acetamide + 2Acetic acid

By formula: C6H9NO3 + 2H2O = C2H5NO + 2C2H4O2

Quantity Value Units Method Reference Comment
Δr-103.5 ± 0.08kJ/molCmHill and Wadso, 1968liquid phase; Heat of hydrolysis; ALS

2Water + Ethene, 1,1-dimethoxy- = Acetic acid + 2Methyl Alcohol

By formula: 2H2O + C4H8O2 = C2H4O2 + 2CH4O

Quantity Value Units Method Reference Comment
Δr-74.4 ± 3.6kJ/molCmGuthrie and Liu, 1995liquid phase; Heat of hydrolysis; ALS

1,3-Dehydroadamantane + Acetic acid = Tricyclo[3.3.1.13,7]decan-1-ol, acetate

By formula: C10H14 + C2H4O2 = C12H18O2

Quantity Value Units Method Reference Comment
Δr-182.0 ± 0.3kJ/molCacWiberg, Connon, et al., 1979liquid phase; solvent: Acetic acid; ALS

Thioacetic acid + Water = Acetic acid + Hydrogen sulfide

By formula: C2H4OS + H2O = C2H4O2 + H2S

Quantity Value Units Method Reference Comment
Δr-2.7 ± 0.3kJ/molCmSunner and Wadso, 1957liquid phase; Heat of hydrolysis; ALS

Acetamide + Water = Acetic acid + Ammonia

By formula: C2H5NO + H2O = C2H4O2 + H3N

Quantity Value Units Method Reference Comment
Δr76.1 ± 1.4kJ/molCmHill and Wadso, 1968solid phase; Heat of hydrolysis; ALS

Acetamide, N-butyl- + Acetic acid = Acetamide, N-acetyl-N-butyl- + Water

By formula: C6H13NO + C2H4O2 = C8H15NO2 + H2O

Quantity Value Units Method Reference Comment
Δr40.5 ± 0.50kJ/molCmWadso, 1965liquid phase; Heat of hydrolysis; ALS

Ethanethioic acid, S-propyl ester + Water = Propyl mercaptan + Acetic acid

By formula: C5H10OS + H2O = C3H8S + C2H4O2

Quantity Value Units Method Reference Comment
Δr-3.9 ± 0.3kJ/molCmWadso, 1957liquid phase; Heat of hydrolysis; ALS

Acetamide, N-phenyl- + Acetic acid = C10H11NO2 + Water

By formula: C8H9NO + C2H4O2 = C10H11NO2 + H2O

Quantity Value Units Method Reference Comment
Δr45.5 ± 0.3kJ/molCmWadso, 1965solid phase; Heat of hydrolysis; ALS

m-Cresyl acetate + Water = Phenol, 3-methyl- + Acetic acid

By formula: C9H10O2 + H2O = C7H8O + C2H4O2

Quantity Value Units Method Reference Comment
Δr-18.4 ± 0.59kJ/molCmSunner, 1957liquid phase; Heat of hydrolysis; ALS

Water + Ethanethioic acid, S-butyl ester = 1-Butanethiol + Acetic acid

By formula: H2O + C6H12OS = C4H10S + C2H4O2

Quantity Value Units Method Reference Comment
Δr-4.6 ± 0.3kJ/molCmWadso, 1957liquid phase; Heat of hydrolysis; ALS

1-Acetyl-1H-tetrazole + Water = 1H-Tetrazole + Acetic acid

By formula: C3H4N4O + H2O = CH2N4 + C2H4O2

Quantity Value Units Method Reference Comment
Δr-43.1 ± 0.4kJ/molCmWadso, 1960solid phase; Heat of hydrolysis; ALS

Benzoic acid, 4-(acetylthio)- + Water = Benzoic acid, 4-mercapto- + Acetic acid

By formula: C9H8O3S + H2O = C7H6O2S + C2H4O2

Quantity Value Units Method Reference Comment
Δr-11.5 ± 0.4kJ/molCmNelander, 1964solid phase; Heat of hydrolysis; ALS

Acetamide, N-phenyl- + Water = Aniline + Acetic acid

By formula: C8H9NO + H2O = C6H7N + C2H4O2

Quantity Value Units Method Reference Comment
Δr-42.0 ± 0.3kJ/molCmWadso, 1965solid phase; Heat of hydrolysis; ALS

Acetic acid + Acetone = 1-Propen-2-ol, acetate + Water

By formula: C2H4O2 + C3H6O = C5H8O2 + H2O

Quantity Value Units Method Reference Comment
Δr60.2 ± 0.3kJ/molCmSunner, 1957liquid phase; Heat of hydrolysis; ALS

S-Ethyl ethanethioate + Water = Acetic acid + Ethanethiol

By formula: C4H8OS + H2O = C2H4O2 + C2H6S

Quantity Value Units Method Reference Comment
Δr-4.0 ± 0.3kJ/molCmWadso, 1957liquid phase; Heat of hydrolysis; ALS

Water + Ethanethioic acid, S-(1-methylethyl) ester = Acetic acid + 2-Propanethiol

By formula: H2O + C5H10OS = C2H4O2 + C3H8S

Quantity Value Units Method Reference Comment
Δr-5.8 ± 0.3kJ/molCmWadso, 1957liquid 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 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)783.7kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity752.8kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.63PITraeger, McLouglin, et al., 1982LBLHLM
10.66EIHolmes, Fingas, et al., 1981LLK
10.66 ± 0.05EIHolmes and Lossing, 1980LLK
10.66EIHolmes and Lossing, 1980, 2LLK
10.66 ± 0.05PIAkopyan and Villem, 1976LLK
10.664 ± 0.003PIWatanabe, Yokoyama, et al., 1974LLK
10.644 ± 0.002PIKnowles and Nicholson, 1974LLK
10.65PEWatanabe, Yokoyama, et al., 1973LLK
10.69 ± 0.03PEThomas, 1972LLK
10.70PESweigart and Turner, 1972LLK
10.37 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
10.38 ± 0.03PIVilesov, 1960RDSH
10.35 ± 0.03PIWatanabe, 1957RDSH
10.9PEVon Niessen, Bieri, et al., 1980Vertical value; LLK
10.84PECarnovale, Gan, et al., 1980Vertical value; LLK
10.63PEBenoit and Harrison, 1977Vertical value; LLK
11.5PERao, 1975Vertical value; LLK
10.87PEKimura, Katsumata, et al., 1975Vertical value; LLK
10.8PEGreen and Hayes, 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C+22.0 ± 0.5H2+HCOOHEIStepanov, Perov, et al., 1988LL
CHO2+12.27 ± 0.05CH3EIHaney and Franklin, 1969RDSH
CHO2+12.9 ± 0.1CH3EIShigorin, Filyugina, et al., 1966RDSH
CH3+14.0 ± 0.15?EIHaney and Franklin, 1969RDSH
CH3O+12.05 ± 0.10CHOEISelim and Helal, 1981LLK
CO+15.3 ± 0.1CH3OHEIShigorin, Filyugina, et al., 1966RDSH
C2H3O+11.54OHPITraeger, McLouglin, et al., 1982LBLHLM
C2H3O+11.75OHEIHaney and Franklin, 1969RDSH
C2H3O+11.4 ± 0.15OHEIShigorin, Filyugina, et al., 1966RDSH
OH+15.1?EIMajer, Patrick, et al., 1961RDSH

De-protonation reactions

MeCO2 anion + Hydrogen cation = Acetic acid

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Δr1457. ± 5.9kJ/molCIDCAngel and Ervin, 2006gas phase; B
Δr1456. ± 9.2kJ/molG+TSTaft and Topsom, 1987gas phase; B
Δr1459. ± 8.8kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Δr1459. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1435.9 ± 2.9kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Δr1427. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; B
Δr1429. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B
Δr1430. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

C2H3O2- + Hydrogen cation = Acetic acid

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Δr1540. ± 13.kJ/molG+TSGrabowski and Cheng, 1989gas phase; B
Δr1539. ± 19.kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Δr1511. ± 13.kJ/molIMRBGrabowski and Cheng, 1989gas 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.

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Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

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French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [all data]

Angel and Ervin, 2006
Angel, L.A.; Ervin, K.M., Gas-phase acidities and O-H bond dissociation enthalpies of phenol, 3-methylphenol, 2,4,6-trimethylphenol, and ethanoic acid, J. Phys. Chem. A, 2006, 110, 35, 10392-10403, https://doi.org/10.1021/jp0627426 . [all data]

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Wadso, 1960
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Wadso, 1957
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Notes

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