Acetic acid

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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:
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
ΔrH°44.1 ± 2.0kcal/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
ΔrS°25.6cal/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
ΔrG°36.5 ± 2.0kcal/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
ΔrH°28.1kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
ΔrH°29.5kcal/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
ΔrS°28.3cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M
ΔrS°27.9cal/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
ΔrG°21.2kcal/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
ΔrH°24.40 ± 0.20kcal/molTDAsSieck, 1985gas phase; B,M
ΔrH°21.6 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B,M
ΔrH°23.9 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°19.6cal/mol*KPHPMSSieck, 1985gas phase; M
ΔrS°24.0cal/mol*KN/ALarson and McMahon, 1984, 2gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
ΔrS°19.3cal/mol*KPHPMSYamdagni and Kebarle, 1971gas phase; M
Quantity Value Units Method Reference Comment
ΔrG°18.60 ± 0.30kcal/molTDAsSieck, 1985gas phase; B
ΔrG°15.8 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B
ΔrG°16.7 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M

MeCO2 anion + Hydrogen cation = Acetic acid

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
ΔrH°348.2 ± 1.4kcal/molCIDCAngel and Ervin, 2006gas phase; B
ΔrH°348.1 ± 2.2kcal/molG+TSTaft and Topsom, 1987gas phase; B
ΔrH°348.6 ± 2.1kcal/molG+TSCumming and Kebarle, 1978gas phase; B
ΔrH°348.7 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
ΔrH°343.20 ± 0.70kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°341.1 ± 2.0kcal/molIMRETaft and Topsom, 1987gas phase; B
ΔrG°341.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
ΔrG°341.7 ± 2.0kcal/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
ΔrH°29.3kcal/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
ΔrS°28.4cal/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
ΔrG°20.8kcal/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
ΔrH°22.0kcal/molPHPMSMeot-Ner, 1984gas phase; M
ΔrH°21.4kcal/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrS°24.3cal/mol*KPHPMSMeot-Ner, 1984gas phase; M
ΔrS°24.cal/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
10.3459.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
ΔrH°12.kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrS°25.cal/mol*KN/AMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
6.2245.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
ΔrH°12.50 ± 0.60kcal/molN/AMeot-ner, Elmore, et al., 1999gas phase; B
ΔrH°16.2 ± 1.0kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°5.73kcal/molTDAsMeot-ner, Elmore, et al., 1999gas phase; B
ΔrG°6.2 ± 1.0kcal/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
ΔrH°19.69 ± 0.50kcal/molN/AMeot-ner, Elmore, et al., 1999gas phase; B
ΔrH°16.2 ± 1.0kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°10.81kcal/molTDAsMeot-ner, Elmore, et al., 1999gas phase; B
ΔrG°6.2 ± 1.0kcal/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
ΔrH°-22.58kcal/molCmDevore and O'Neal, 1969liquid phase; Heat of hydrolysis; ALS
ΔrH°-22.06kcal/molCmPritchard and Skinner, 1950liquid phase; Heat of hydrolysis at 298 K, see Carson and Skinner, 1949; ALS
ΔrH°-22.09kcal/molCmCarson and Skinner, 1949liquid phase; ALS

Acetic anhydride + Water = 2Acetic acid

By formula: C4H6O3 + H2O = 2C2H4O2

Quantity Value Units Method Reference Comment
ΔrH°-13.53 ± 0.96kcal/molCmBecker and Maelicke, 1967liquid phase; ALS
ΔrH°-14.00 ± 0.09kcal/molCmWadso, 1962liquid phase; ALS
ΔrH°-14.0 ± 0.1kcal/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
ΔrH°16.9 ± 1.0kcal/molTDAsCaldwell and Kebarle, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°21.3cal/mol*KPHPMSCaldwell and Kebarle, 1984gas phase; M
Quantity Value Units Method Reference Comment
ΔrG°10.5 ± 1.0kcal/molTDAsCaldwell and Kebarle, 1984gas phase; B

C2H3O2- + Hydrogen cation = Acetic acid

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
ΔrH°368.0 ± 3.1kcal/molG+TSGrabowski and Cheng, 1989gas phase; B
ΔrH°367.8 ± 4.6kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°361.2 ± 3.0kcal/molIMRBGrabowski and Cheng, 1989gas phase; B

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

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

Quantity Value Units Method Reference Comment
ΔrH°22.60 ± 0.10kcal/molTDAsSieck, 1985gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°26.8cal/mol*KPHPMSSieck, 1985gas phase; M
Quantity Value Units Method Reference Comment
ΔrG°14.60 ± 0.20kcal/molTDAsSieck, 1985gas phase; B

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

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

Quantity Value Units Method Reference Comment
ΔrH°27.4kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M
Quantity Value Units Method Reference Comment
ΔrS°24.0cal/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
ΔrH°13.1kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°22.4cal/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
ΔrH°18.5kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°24.5cal/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
ΔrH°18.1kcal/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°27.2cal/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

Diacetamide + Water = Acetamide + Acetic acid

By formula: C4H7NO2 + H2O = C2H5NO + C2H4O2

Quantity Value Units Method Reference Comment
ΔrH°-4.33 ± 0.05kcal/molCmHill and Wadso, 1968solid phase; Heat of hydrolysis; ALS
ΔrH°-4.33 ± 0.05kcal/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
ΔrH°18.4kcal/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°24.7cal/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
ΔrH°-22.46kcal/molCmDevore and O'Neal, 1969liquid phase; Heat of hydrolysis; ALS
ΔrH°-21.59kcal/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
ΔrH°29.3 ± 1.0kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°20.4 ± 1.6kcal/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
ΔrH°-27.06 ± 0.11kcal/molCmWadso, 1962liquid phase; ALS
ΔrH°-39.13 ± 0.06kcal/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
ΔrH°-23.31kcal/molCmDevore and O'Neal, 1969liquid phase; Heat of hydrolysis; ALS
ΔrH°-23.06kcal/molCmCarson and Skinner, 1949liquid phase; ALS

thiophenoxide anion + Acetic acid = C8H9O2S-

By formula: C6H5S- + C2H4O2 = C8H9O2S-

Quantity Value Units Method Reference Comment
ΔrH°20.30 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°12.50 ± 0.40kcal/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
ΔrH°16.2kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°33.2cal/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
ΔrH°19.6kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°28.6cal/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
ΔrH°20.3kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°26.2cal/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
ΔrH°41.5kcal/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
ΔrH°29.3kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°29.6cal/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
ΔrH°-5.33 ± 0.50kcal/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
ΔrH°-4.83 ± 0.05kcal/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
ΔrH°5.330kcal/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
ΔrH°0.441kcal/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
ΔrH°-24.74 ± 0.02kcal/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
ΔrH°-17.79 ± 0.86kcal/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
ΔrH°-43.49 ± 0.08kcal/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
ΔrH°-0.64 ± 0.07kcal/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
ΔrH°18.2 ± 0.33kcal/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
ΔrH°9.68 ± 0.12kcal/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
ΔrH°-0.93 ± 0.06kcal/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
ΔrH°10.88 ± 0.07kcal/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
ΔrH°-4.39 ± 0.14kcal/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
ΔrH°-1.09 ± 0.06kcal/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
ΔrH°-10.31 ± 0.09kcal/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
ΔrH°-2.75 ± 0.09kcal/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
ΔrH°-10.05 ± 0.06kcal/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
ΔrH°14.39 ± 0.06kcal/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
ΔrH°-0.95 ± 0.06kcal/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
ΔrH°-1.39 ± 0.07kcal/molCmWadso, 1957liquid phase; Heat of hydrolysis; ALS

References

Go To: Top, Reaction thermochemistry 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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Lias, Liebman, et al., 1984
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Yamdagni and Kebarle, 1971
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French, Ikuta, et al., 1982
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Angel and Ervin, 2006
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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, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

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Meot-Ner and Sieck, 1986
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Devore and O'Neal, 1969
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Pritchard and Skinner, 1950
Pritchard, H.O.; Skinner, H.A., The heats of hydrolysis of the chloro-substituted acetyl chlorides, J. Chem. Soc., 1950, 272-276. [all data]

Carson and Skinner, 1949
Carson, A.S.; Skinner, H.A., 201. Carbon-halogen bond energies in the acetyl halides, J. Chem. Soc., 1949, 936-939. [all data]

Becker and Maelicke, 1967
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Wadso, 1962
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Conn, Kistiakowsky, et al., 1942
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Wadso, 1965
Wadso, I., Thermochemical properties of diacetimide, N-butyldiacetimide and N-phenyldiacetimide, Acta Chem. Scand., 1965, 19, 1079-1087. [all data]

Wadso, 1958
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Sieck and Meot-ner, 1989
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Staley and Beauchamp, 1975
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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, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [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, Can. J. Chem., 1995, 73, 1395-2398. [all data]

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, J. Am. Chem. Soc., 1979, 101, 6970-6972. [all data]

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]

Notes

Go To: Top, Reaction thermochemistry data, References