Propanoic acid, 2-methyl-

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Condensed phase 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 by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
181.7298.15Biros, Sikora, et al., 1982T = 270 to 370 K. Equation only. Cp = 130.1 - 0.08156 T + 0.0008541 T2 J/mol*K.
173.298.15Konicek and Wadso, 1971 
171.1298.von Reis, 1881T = 291 to 448 K.

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
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

Quantity Value Units Method Reference Comment
Tboil427. ± 2.KAVGN/AAverage of 40 out of 42 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus227. ± 2.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tc605.KN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 1.5 K; TRC
Tc609.40KN/ABrown, 1906Uncertainty assigned by TRC = 6. K; TRC
Quantity Value Units Method Reference Comment
Pc37.00barN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 0.25 bar; TRC
Quantity Value Units Method Reference Comment
Δvap56.3kJ/molCGCVerevkin, 2000Based on data from 303. to 378. K.; AC
Δvap55.5 ± 0.3kJ/molGSVerevkin, 2000Based on data from 278. to 308. K.; AC
Δvap53.kJ/molN/AMajer and Svoboda, 1985 
Δvap53.4 ± 3.0kJ/molVKruif and Oonk, 1979ALS
Δvap53. ± 4.kJ/molCKonicek, Wadsö, et al., 1970AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
50.5390.N/AClifford, Ramjugernath, et al., 2004Based on data from 375. to 426. K.; AC
55.8 ± 0.3293.GSVerevkin, 2000Based on data from 278. to 308. K.; AC
51.6359.EBAmbrose and Ghiassee, 1987, 2Based on data from 344. to 445. K.; AC
50.9303.AStephenson and Malanowski, 1987Based on data from 288. to 428. K.; AC
45.4443.AStephenson and Malanowski, 1987Based on data from 428. to 562. K.; AC
53. ± 3.398.TEKruif and Oonk, 1979Based on data from 228. to 243. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
330.7 to 425.2.23908459.215-220.378Kahlbaum, 1883Coefficents calculated by NIST from author's data.

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

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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.

Individual Reactions

Iodide + Propanoic acid, 2-methyl- = (Iodide • Propanoic acid, 2-methyl-)

By formula: I- + C4H8O2 = (I- • C4H8O2)

Quantity Value Units Method Reference Comment
Δr69.9 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Δr85.8J/mol*KPHPMSCaldwell and Kebarle, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr44.4 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B

iPrCO2 anion + Propanoic acid, 2-methyl- = (iPrCO2 anion • Propanoic acid, 2-methyl-)

By formula: C4H7O2- + C4H8O2 = (C4H7O2- • C4H8O2)

Quantity Value Units Method Reference Comment
Δr125. ± 4.2kJ/molN/AMeot-Ner and Sieck, 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Δr140.J/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr83.3 ± 6.7kJ/molTDAsMeot-Ner and Sieck, 1986gas phase; B

iPrCO2 anion + Hydrogen cation = Propanoic acid, 2-methyl-

By formula: C4H7O2- + H+ = C4H8O2

Quantity Value Units Method Reference Comment
Δr1448. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr1418. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B

Hydrogen + 2-Propenoic acid, 2-methyl- = Propanoic acid, 2-methyl-

By formula: H2 + C4H6O2 = C4H8O2

Quantity Value Units Method Reference Comment
Δr-118. ± 1.kJ/molChydSkinner and Snelson, 1959liquid phase; solvent: Acetic acid; ALS

Water + Propanoic acid, 2-methyl-, anhydride = 2Propanoic acid, 2-methyl-

By formula: H2O + C8H14O3 = 2C4H8O2

Quantity Value Units Method Reference Comment
Δr-61.04kJ/molCmConn, Kistiakowsky, et al., 1942liquid phase; Heat of hydrolysis at 303 K; ALS

Methyl isobutyrate + Water = Methyl Alcohol + Propanoic acid, 2-methyl-

By formula: C5H10O2 + H2O = CH4O + C4H8O2

Quantity Value Units Method Reference Comment
Δr-61.6 ± 1.0kJ/molEqkGuthrie and Cullimore, 1980liquid phase; ALS

Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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 C4H8O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)10.24 ± 0.12eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
10.12EIHolmes and Lossing, 1980LLK
10.329 ± 0.005PIWatanabe, Yokoyama, et al., 1974LLK
10.33PEWatanabe, Yokoyama, et al., 1973LLK
10.33 ± 0.03PEThomas, 1972LLK
10.02 ± 0.05PIWatanabe, Nakayama, et al., 1962RDSH
10.30PESustmann and Trill, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHO2+11.28C3H7EIHolmes, Lossing, et al., 1991LL

De-protonation reactions

iPrCO2 anion + Hydrogen cation = Propanoic acid, 2-methyl-

By formula: C4H7O2- + H+ = C4H8O2

Quantity Value Units Method Reference Comment
Δr1448. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr1418. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B

Ion clustering 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

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

iPrCO2 anion + Propanoic acid, 2-methyl- = (iPrCO2 anion • Propanoic acid, 2-methyl-)

By formula: C4H7O2- + C4H8O2 = (C4H7O2- • C4H8O2)

Quantity Value Units Method Reference Comment
Δr125. ± 4.2kJ/molN/AMeot-Ner and Sieck, 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Δr140.J/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr83.3 ± 6.7kJ/molTDAsMeot-Ner and Sieck, 1986gas phase; B

Iodide + Propanoic acid, 2-methyl- = (Iodide • Propanoic acid, 2-methyl-)

By formula: I- + C4H8O2 = (I- • C4H8O2)

Quantity Value Units Method Reference Comment
Δr69.9 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Δr85.8J/mol*KPHPMSCaldwell and Kebarle, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr44.4 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B

References

Go To: Top, 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.

Biros, Sikora, et al., 1982
Biros, J.; Sikora, A.; Zivny, A.; Pouchly, J., Heat capacity of monomer models of some hydrophilic polymers in aqueous solution from 20° to 60°C, Collect Czech. Chem. Commun., 1982, 47(10), 2692-2701. [all data]

Konicek and Wadso, 1971
Konicek, J.; Wadso, I., Thermochemical properties of some carboxylic acids, amines and N-substituted amides in aqueous solution, Acta Chem. Scand., 1971, 25, 1541-1551. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Ambrose and Ghiassee, 1987
Ambrose, D.; Ghiassee, N.B., Vapor Pressures and Critical Temperatures and Critical Pressures of Some Alkanoic Acids: C1 to C10, J. Chem. Thermodyn., 1987, 19, 505. [all data]

Brown, 1906
Brown, J.C., The critical temperature and value of ml/theta of some carbon compounds, J. Chem. Soc., Trans., 1906, 89, 311. [all data]

Verevkin, 2000
Verevkin, S.P., Measurement and Prediction of the Monocarboxylic Acids Thermochemical Properties, J. Chem. Eng. Data, 2000, 45, 5, 953-960, https://doi.org/10.1021/je990282m . [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Kruif and Oonk, 1979
Kruif, C.G.; Oonk, H.A.J., Enthalpies of vaporization and vapour pressures of seven aliphatic carboxylic acids, J. Chem. Thermodyn., 1979, 11, 287-290. [all data]

Konicek, Wadsö, et al., 1970
Konicek, Jiri; Wadsö, Ingemar; Munch-Petersen, J.; Ohlson, Ragnar; Shimizu, Akira, Enthalpies of Vaporization of Organic Compounds. VII. Some Carboxylic Acids., Acta Chem. Scand., 1970, 24, 2612-2616, https://doi.org/10.3891/acta.chem.scand.24-2612 . [all data]

Clifford, Ramjugernath, et al., 2004
Clifford, Scott L.; Ramjugernath, Deresh; Raal, J. David, Subatmospheric Vapor Pressure Curves for Propionic Acid, Butyric Acid, Isobutyric Acid, Valeric Acid, Isovaleric Acid, Hexanoic Acid, and Heptanoic Acid, J. Chem. Eng. Data, 2004, 49, 5, 1189-1192, https://doi.org/10.1021/je034180e . [all data]

Ambrose and Ghiassee, 1987, 2
Ambrose, D.; Ghiassee, N.B., Vapour pressures and critical temperatures and critical pressures of some alkanoic acids: C1 to C10, The Journal of Chemical Thermodynamics, 1987, 19, 5, 505-519, https://doi.org/10.1016/0021-9614(87)90147-9 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Kahlbaum, 1883
Kahlbaum, Georg W.A., Ueber die Abhängigkeit der Siedetemperatur vom Luftdruck, Ber. Dtsch. Chem. Ges., 1883, 16, 2, 2476-2484, https://doi.org/10.1002/cber.188301602178 . [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]

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]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

Skinner and Snelson, 1959
Skinner, H.A.; Snelson, A., Heats of hydrogenation Part 3., Trans. Faraday Soc., 1959, 55, 405-407. [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]

Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A., Effect of the acyl substituent on the equilibrium constant for hydration of esters, Can. J. Chem., 1980, 58, 1281-1294. [all data]

Holmes and Lossing, 1980
Holmes, J.L.; Lossing, F.P., Gas-phase heats of formation of keto and enol ions of carbonyl compounds., J. Am. Chem. Soc., 1980, 102, 1591. [all data]

Watanabe, Yokoyama, et al., 1974
Watanabe, I.; Yokoyama, Y.; Ikeda, S., Vibrational structures in the He(I) photoelectron spectra of carboxylic acids, Bull. Chem. Soc. Jpn., 1974, 47, 627. [all data]

Watanabe, Yokoyama, et al., 1973
Watanabe, I.; Yokoyama, Y.; Ikeda, S., Lone pair ionization potentials of carboxylic acids determined by He(I) photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1973, 46, 1959. [all data]

Thomas, 1972
Thomas, R.K., Photoelectron spectroscopy of hydrogen-bonded systems: spectra of monomers, dimers and mixed complexes of carboxylic acides, Proc. R. Soc. London A:, 1972, 331, 249. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Sustmann and Trill, 1972
Sustmann, R.; Trill, H., Photoelektronenspektroskopische Bestimmung von Substituenten-Effekten. II. α,β-ungesattigte Carbonester, Tetrahedron Lett., 1972, 42, 4271. [all data]

Holmes, Lossing, et al., 1991
Holmes, J.L.; Lossing, F.P.; Mayer, P.M., Heats of formation of oxygen-containing organic free radicals from appearance energy measurements, J. Am. Chem. Soc., 1991, 113, 9723. [all data]


Notes

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