Acetic acid

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), 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:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
ΔfH°gas-103.5 ± 0.6kcal/molAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
S°gas67.600cal/mol*KN/AWeltner W., 1955Other third-law entropy values at 298.15 K are 284.5 [ Chao J., 1986] and 290.37(4.18) J/mol*K [ Halford J.O., 1941].; GT

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
9.45050.Chao J., 1986p=1 bar. Selected entropies and heat capacities differ from other statistically calculated values [ Weltner W., 1955] by 1.0-1.3 J/mol*K for S(T) and 3.1-5.4 J/mol*K for Cp(T). Please also see Chao J., 1978.; GT
9.661100.
10.22150.
11.55200.
14.19273.15
15.16 ± 0.026298.15
15.23300.
19.04400.
22.45500.
25.378600.
27.875700.
29.995800.
31.785900.
33.2841000.
34.5271100.
35.5541200.
36.4011300.
37.0981400.
37.6741500.

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Mass spectrum (electron ionization), 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
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

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, 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 compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 80
NIST MS number 227635

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Weltner W., 1955
Weltner W., Jr., The vibrational spectrum, associative and thermodynamic properties of acetic acid vapor, J. Am. Chem. Soc., 1955, 77, 3941-3950. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Halford J.O., 1941
Halford J.O., The entropy of acetic acid, J. Chem. Phys., 1941, 9, 859-863. [all data]

Chao J., 1978
Chao J., Ideal gas thermodynamic properties of methanoic and ethanoic acids, J. Phys. Chem. Ref. Data, 1978, 7, 363-377. [all data]

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]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Bond dissociation energies of F2(-) and HF2(-). A gas-phase experimental and G2 theoretical study, J. Phys. Chem., 1995, 99, 7, 2002, https://doi.org/10.1021/j100007a034 . [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

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 Wärmefluβkalorimetrie, Z. Phys. Chem. (Neue Folge), 1967, 55, 280-295. [all data]

Wadso, 1962
Wadso, I., Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride, Acta Chem. Scand., 1962, 16, 471-478. [all data]

Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A., Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides, J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]

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, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), References