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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 bullet Acetic acid)

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

Quantity Value Units Method Reference Comment
Deltar44.1 ± 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
Deltar25.6cal/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
Deltar36.5 ± 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+ bullet Acetic acid)

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

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

Quantity Value Units Method Reference Comment
Deltar28.1kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Deltar29.5kcal/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
Deltar28.3cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M
Deltar27.9cal/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
Deltar21.2kcal/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 bullet Acetic acid)

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

Quantity Value Units Method Reference Comment
Deltar24.40 ± 0.20kcal/molTDAsSieck, 1985gas phase; B,M
Deltar21.6 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B,M
Deltar23.9 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar19.6cal/mol*KPHPMSSieck, 1985gas phase; M
Deltar24.0cal/mol*KN/ALarson and McMahon, 1984, 2gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Deltar19.3cal/mol*KPHPMSYamdagni and Kebarle, 1971gas phase; M
Quantity Value Units Method Reference Comment
Deltar18.60 ± 0.30kcal/molTDAsSieck, 1985gas phase; B
Deltar15.8 ± 2.0kcal/molTDAsYamdagni and Kebarle, 1971gas phase; B
Deltar16.7 ± 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
Deltar348.2 ± 1.4kcal/molCIDCAngel and Ervin, 2006gas phase; B
Deltar348.1 ± 2.2kcal/molG+TSTaft and Topsom, 1987gas phase; B
Deltar348.6 ± 2.1kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Deltar348.7 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar343.20 ± 0.70kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Deltar341.1 ± 2.0kcal/molIMRETaft and Topsom, 1987gas phase; B
Deltar341.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
Deltar341.7 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

C2H7O+ + Acetic acid = (C2H7O+ bullet Acetic acid)

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

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

Quantity Value Units Method Reference Comment
Deltar29.3kcal/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
Deltar28.4cal/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
Deltar20.8kcal/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+ bullet Acetic acid)

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

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

Quantity Value Units Method Reference Comment
Deltar22.0kcal/molPHPMSMeot-Ner, 1984gas phase; M
Deltar21.4kcal/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar24.3cal/mol*KPHPMSMeot-Ner, 1984gas phase; M
Deltar24.cal/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
10.3459.PHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

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

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

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

Quantity Value Units Method Reference Comment
Deltar12.kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar25.cal/mol*KN/AMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.2245.PHPMSMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated; M

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

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

Quantity Value Units Method Reference Comment
Deltar12.50 ± 0.60kcal/molN/AMeot-ner, Elmore, et al., 1999gas phase; B
Deltar16.2 ± 1.0kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar5.73kcal/molTDAsMeot-ner, Elmore, et al., 1999gas phase; B
Deltar6.2 ± 1.0kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar19.69 ± 0.50kcal/molN/AMeot-ner, Elmore, et al., 1999gas phase; B
Deltar16.2 ± 1.0kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar10.81kcal/molTDAsMeot-ner, Elmore, et al., 1999gas phase; B
Deltar6.2 ± 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
Deltar-22.58kcal/molCmDevore and O'Neal, 1969liquid phase; Heat of hydrolysis; ALS
Deltar-22.06kcal/molCmPritchard and Skinner, 1950liquid phase; Heat of hydrolysis at 298 K, see Carson and Skinner, 1949; ALS
Deltar-22.09kcal/molCmCarson and Skinner, 1949liquid phase; ALS

Acetic anhydride + Water = 2Acetic acid

By formula: C4H6O3 + H2O = 2C2H4O2

Quantity Value Units Method Reference Comment
Deltar-13.53 ± 0.96kcal/molCmBecker and Maelicke, 1967liquid phase; ALS
Deltar-14.00 ± 0.09kcal/molCmWadso, 1962liquid phase; ALS
Deltar-14.0 ± 0.1kcal/molCmConn, Kistiakowsky, et al., 1942liquid phase; Heat of hydrolysis at 303 K; ALS

Iodide + Acetic acid = (Iodide bullet Acetic acid)

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

Quantity Value Units Method Reference Comment
Deltar16.9 ± 1.0kcal/molTDAsCaldwell and Kebarle, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar21.3cal/mol*KPHPMSCaldwell and Kebarle, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar10.5 ± 1.0kcal/molTDAsCaldwell and Kebarle, 1984gas phase; B

C2H3O2- + Hydrogen cation = Acetic acid

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Deltar368.0 ± 3.1kcal/molG+TSGrabowski and Cheng, 1989gas phase; B
Deltar367.8 ± 4.6kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Deltar361.2 ± 3.0kcal/molIMRBGrabowski and Cheng, 1989gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar22.60 ± 0.10kcal/molTDAsSieck, 1985gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar26.8cal/mol*KPHPMSSieck, 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar14.60 ± 0.20kcal/molTDAsSieck, 1985gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar27.4kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M
Quantity Value Units Method Reference Comment
Deltar24.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M

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

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

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

Quantity Value Units Method Reference Comment
Deltar13.1kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
Deltar22.4cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M

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

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

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

Quantity Value Units Method Reference Comment
Deltar18.5kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
Deltar24.5cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M

C6H12NO3+ + Acetic acid = (C6H12NO3+ bullet Acetic acid)

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar18.1kcal/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Deltar27.2cal/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

Diacetamide + Water = Acetamide + Acetic acid

By formula: C4H7NO2 + H2O = C2H5NO + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-4.33 ± 0.05kcal/molCmHill and Wadso, 1968solid phase; Heat of hydrolysis; ALS
Deltar-4.33 ± 0.05kcal/molCmWadso, 1965solid phase; Heat of hydrolysis; ALS

C4H10NO+ + Acetic acid = (C4H10NO+ bullet Acetic acid)

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

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

Quantity Value Units Method Reference Comment
Deltar18.4kcal/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Deltar24.7cal/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
Deltar-22.46kcal/molCmDevore and O'Neal, 1969liquid phase; Heat of hydrolysis; ALS
Deltar-21.59kcal/molCmCarson and Skinner, 1949liquid phase; Heat of hydrolysis; ALS

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

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

Quantity Value Units Method Reference Comment
Deltar29.3 ± 1.0kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar20.4 ± 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
Deltar-27.06 ± 0.11kcal/molCmWadso, 1962liquid phase; ALS
Deltar-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
Deltar-23.31kcal/molCmDevore and O'Neal, 1969liquid phase; Heat of hydrolysis; ALS
Deltar-23.06kcal/molCmCarson and Skinner, 1949liquid phase; ALS

thiophenoxide anion + Acetic acid = C8H9O2S-

By formula: C6H5S- + C2H4O2 = C8H9O2S-

Quantity Value Units Method Reference Comment
Deltar20.30 ± 0.10kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar12.50 ± 0.40kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar16.2kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar33.2cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar19.6kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar28.6cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar20.3kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar26.2cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar41.5kcal/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 interpolated; M

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

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

Quantity Value Units Method Reference Comment
Deltar29.3kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar29.6cal/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
Deltar-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
Deltar-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
Deltar5.330kcal/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
Deltar0.441kcal/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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar18.2 ± 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
Deltar9.68 ± 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
Deltar-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
Deltar10.88 ± 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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar14.39 ± 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
Deltar-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
Deltar-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.

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

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Arshadi, Yamdagni, et al., 1970
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Meot-Ner (Mautner), 1992
Meot-Ner (Mautner), M., Intermolecular Forces in Organic Clusters, J. Am. Chem. Soc., 1992, 114, 9, 3312, https://doi.org/10.1021/ja00035a024 . [all data]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Keesee and Castleman, 1986
Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [all data]

Sieck, 1985
Sieck, L.W., Thermochemistry of Solvation of NO2- and C6H5NO2- by Polar Molecules in the Vapor Phase. Comparison with Cl- and Variation with Ligand Structure., J. Phys. Chem., 1985, 89, 25, 5552, https://doi.org/10.1021/j100271a049 . [all data]

Yamdagni and Kebarle, 1971
Yamdagni, R.; Kebarle, P., Hydrogen bonding energies to negative ions from gas phase measurements of ionic equilibria, J. Am. Chem. Soc., 1971, 93, 7139. [all data]

Larson and McMahon, 1984
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]

Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [all data]

French, Ikuta, et al., 1982
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]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

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]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A., Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry, Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C . [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., 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, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Meot-ner, Elmore, et al., 1999
Meot-ner, M.; Elmore, D.E.; Scheiner, S., Ionic Hydrogen Bond Effects on the Acidities, Basicities, Solvation, Solvent Bridging and Self-assembly of Carboxylic Groups, J. Am. Chem. Soc., 1999, 121, 33, 7625, https://doi.org/10.1021/ja982173i . [all data]

Meot-Ner and Sieck, 1986
Meot-Ner, M.; Sieck, L.W., The ionic hydrogen bond and ion solvation. 5. OH...O- bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions, J. Am. Chem. Soc., 1986, 108, 7525. [all data]

Devore and O'Neal, 1969
Devore, J.A.; O'Neal, H.E., Heats of formation of the acetyl halides and of the acetyl radical, J. Phys. Chem., 1969, 73, 2644-2648. [all data]

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
Becker, F.; Maelicke, A., Thermokinetische Messungen nach dem Prinzip der Wärmeflu«beta»kalorimetrie, 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]

Caldwell and Kebarle, 1984
Caldwell, G.; Kebarle, P., Binding energies and structural effects in halide anion-ROH and -RCOOH complexes from gas phase equilibria measurements, J. Am. Chem. Soc., 1984, 106, 967. [all data]

Grabowski and Cheng, 1989
Grabowski, J.J.; Cheng, X., Gas-Phase Formation of the Enolate Monoanion of Acetic Acid by Proton Abstraction, J. Am. Chem. Soc., 1989, 111, 8, 3106, https://doi.org/10.1021/ja00190a078 . [all data]

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, J. Am. Chem. Soc., 1984, 106, 2, 278, https://doi.org/10.1021/ja00314a003 . [all data]

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., J. Phys. Chem., 1989, 93, 4, 1586, https://doi.org/10.1021/j100341a079 . [all data]

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, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

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