Acetic acid

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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:
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.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
ΔfH°liquid-115.56 ± 0.086kcal/molCcbSteele, Chirico, et al., 1997ALS
ΔfH°liquid-115.80 ± 0.05kcal/molCcbLebedeva, 1964ALS
ΔfH°liquid-115.7 ± 0.1kcal/molCcbEvans and Skinner, 1959ALS
ΔfH°liquid-116.4kcal/molCmCarson and Skinner, 1949Unpublished result by Rossini; ALS
Quantity Value Units Method Reference Comment
ΔcH°liquid-209.17 ± 0.081kcal/molCcbSteele, Chirico, et al., 1997Corresponding ΔfHºliquid = -115.56 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
ΔcH°liquid-208.94 ± 0.05kcal/molCcbLebedeva, 1964Corresponding ΔfHºliquid = -115.79 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
ΔcH°liquid-209.0 ± 0.1kcal/molCcbEvans and Skinner, 1959Corresponding ΔfHºliquid = -115.7 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
ΔcH°liquid-208.5kcal/molCcbSchjanberg, 1935Corresponding ΔfHºliquid = -116.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
S°liquid37.76cal/mol*KN/AMartin and Andon, 1982DH
S°liquid46.30cal/mol*KN/AParks and Kelley, 1925Extrapolation below 90 K. 76.82 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
29.42298.15Martin and Andon, 1982T = 13 to 450 K. Data also given by equation.; DH
33.39332.Swietoslawski and Zielenkiewicz, 1958Mean value 22 to 96°C.; DH
28.80298.Radulescu and Jula, 1934DH
28.99297.1Neumann, 1932T = 23.9 to 80.5°C. Value is unsmoothed experimental datum.; DH
38.19298.1Parks, Kelley, et al., 1929Extrapolation below 90 K, 42.68 J/mol*K. Revision of previous data.; DH
29.49294.7Parks and Kelley, 1925T = 87 to 295 K. Value is unsmoothed experimental datum.; DH
32.7287. to 335.Pickering, 1895T = 260 to 335 K.; DH
29.52298.von Reis, 1881T = 292 to 358 K.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil391.2 ± 0.6KAVGN/AAverage of 80 out of 90 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus289.6 ± 0.5KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple289.8KN/AWilhoit, Chao, et al., 1985Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple289.69KN/AMartin and Andon, 1982, 2Uncertainty assigned by TRC = 0.04 K; TRC
Ttriple289.8KN/AParks and Kelley, 1925, 2Uncertainty assigned by TRC = 0.15 K; TRC
Quantity Value Units Method Reference Comment
Tc593. ± 3.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Pc57.05atmN/AAndereya and Chase, 1990Uncertainty assigned by TRC = 0.20 atm; TRC
Pc57.5279atmN/AD'Souza and Teja, 1987Uncertainty assigned by TRC = 0.89 atm; Ambrose's procedure; TRC
Pc57.10atmN/AAmbrose, Ellender, et al., 1977Uncertainty assigned by TRC = 0.08 atm; TRC
Pc57.11atmN/AYoung, 1910Uncertainty assigned by TRC = 0.99995 atm; TRC
Pc57.110atmN/AYoung, 1891Uncertainty assigned by TRC = 0.2631 atm; TRC
Quantity Value Units Method Reference Comment
ρc5.84mol/lN/AVandana and Teja, 1995Uncertainty assigned by TRC = 0.02 mol/l; TRC
ρc5.838mol/lN/AYoung, 1910Uncertainty assigned by TRC = 0.02 mol/l; TRC
Quantity Value Units Method Reference Comment
ΔvapH°12.0kcal/molCGCVerevkin, 2000Based on data from 303. to 378. K.; AC
ΔvapH°12.3kcal/molN/AMajer and Svoboda, 1985 
ΔvapH°12.3 ± 0.36kcal/molCKonicek and Wadso, 1970ALS
ΔvapH°12.3 ± 0.38kcal/molCKonicek, Wadsö, et al., 1970AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
5.66391.1N/AMajer and Svoboda, 1985 
9.35360.EBMuñoz and Krähenbühl, 2001Based on data from 345. to 383. K.; AC
9.78335.N/AVercher, Vázquez, et al., 2001Based on data from 320. to 395. K.; AC
9.06406.AStephenson and Malanowski, 1987Based on data from 391. to 550. K.; AC
10.0305.AStephenson and Malanowski, 1987Based on data from 290. to 396. K.; AC
9.25406.AStephenson and Malanowski, 1987Based on data from 391. to 447. K.; AC
9.11452.AStephenson and Malanowski, 1987Based on data from 437. to 535. K.; AC
9.27540.AStephenson and Malanowski, 1987Based on data from 525. to 593. K.; AC
9.94304.AStephenson and Malanowski, 1987Based on data from 289. to 392. K. See also Dykyj, 1970.; AC
10.3308.N/ATamir, Dragoescu, et al., 1983AC
9.63340.N/AMcDonald, Shrader, et al., 1959Based on data from 325. to 391. K.; AC
9.94318.MMPotter and Ritter, 1954Based on data from 303. to 399. K.; AC

Enthalpy of vaporization

ΔvapH = A exp(-αTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) 298. to 392.
A (kcal/mol) 5.459
α 0.0184
β -0.0454
Tc (K) 592.7
ReferenceMajer and Svoboda, 1985

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference
290.26 to 391.014.676351642.54-39.764McDonald, Shrader, et al., 1959

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
16.1 ± 0.2223.TE,MECalis-Van Ginkel, Calis, et al., 1978Based on data from 213. to 230. K.; AC
17. ± 0.2213.TE,MECalis-Van Ginkel, Calis, et al., 1978Based on data from 213. to 230. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.801298.7Domalski and Hearing, 1996See also Martin and Andon, 1982.; AC
2.8031289.9Parks and Kelley, 1925DH
2.588289.8Louguinine and Dupont, 1911AC
2.753283.7Meyer, 1910AC
2.6592290.06Pickering, 1895DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
9.673289.9Parks and Kelley, 1925DH
9.168290.06Pickering, 1895DH

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
2.8011298.69crystaline, IliquidMartin and Andon, 1982DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
9.68298.69crystaline, IliquidMartin and Andon, 1982DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering 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
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

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering 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)187.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity179.9kcal/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
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

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

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

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

CO3- + Acetic acid = C3H4O5-

By formula: CO3- + C2H4O2 = C3H4O5-

Quantity Value Units Method Reference Comment
ΔrG°11.30 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 1998gas phase; B

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

(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

(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 • 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

(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 • 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

C2H4NO5- + Water + Acetic acid = C2H6NO6-

By formula: C2H4NO5- + H2O + C2H4O2 = C2H6NO6-

Quantity Value Units Method Reference Comment
ΔrG°4.60 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 2000gas phase; B

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

(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

(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+ • 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

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

C3H4O5- + Water + Acetic acid = C3H6O6-

By formula: C3H4O5- + H2O + C2H4O2 = C3H6O6-

Quantity Value Units Method Reference Comment
ΔrG°4.60 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 2000gas phase; B

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

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

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

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

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

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

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

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

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

Nitrogen oxide anion + Acetic acid = C2H4NO4-

By formula: NO2- + C2H4O2 = C2H4NO4-

Quantity Value Units Method Reference Comment
ΔrG°12.20 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 1998gas phase; B

NO3 anion + Acetic acid = C2H4NO5-

By formula: NO3- + C2H4O2 = C2H4NO5-

Quantity Value Units Method Reference Comment
ΔrG°11.80 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 1998gas phase; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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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Meot-Ner, 1984
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Meot-ner, Elmore, et al., 1999
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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
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Becker and Maelicke, 1967
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Wadso, 1962
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Conn, Kistiakowsky, et al., 1942
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Caldwell and Kebarle, 1984
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Grabowski and Cheng, 1989
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Meot-Ner, 1984, 2
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Hill and Wadso, 1968
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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
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
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Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, 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
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Notes

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