Propanoic acid

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Gas 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: Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Δfgas-455.8 ± 2.0kJ/molN/ALebedeva, 1964Value computed using ΔfHliquid° value of -510.8±0.1 kj/mol from Lebedeva, 1964 and ΔvapH° value of 55±2 kj/mol from missing citation.
Δfgas-455.8 ± 2.0kJ/molCcbLebedeva, 1964Value computed using ΔfHliquid° from Lebedeva, 1964 and ΔvapH° value of 55. kJ/mol from Konicek and Wadso, 1970.
Δfgas-455.0 ± 3.2kJ/molCcbSchjanberg, 1935Value computed using ΔfHliquid° from Schjanberg, 1935 and ΔvapH° value of 55. kJ/mol from Konicek and Wadso, 1970. estimated uncertainty

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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

EtCO2 anion + Hydrogen cation = Propanoic acid

By formula: C3H5O2- + H+ = C3H6O2

Quantity Value Units Method Reference Comment
Δr1454. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr1454. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr1424. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr1424. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

Iodide + Propanoic acid = (Iodide • Propanoic acid)

By formula: I- + C3H6O2 = (I- • C3H6O2)

Quantity Value Units Method Reference Comment
Δr69.5 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B
Quantity Value Units Method Reference Comment
Δr43.9 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B

thiophenoxide anion + Propanoic acid = C9H11O2S-

By formula: C6H5S- + C3H6O2 = C9H11O2S-

Quantity Value Units Method Reference Comment
Δr83.7 ± 1.7kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr51.9 ± 5.4kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

Ethanol + Propanoic acid = Propanoic acid, ethyl ester + Water

By formula: C2H6O + C3H6O2 = C5H10O2 + H2O

Quantity Value Units Method Reference Comment
Δr-22.6 ± 0.42kJ/molEqkEssex and Sandholzer, 1938liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -23.54 kJ/mol; ALS

Propanoic acid, anhydride + Water = 2Propanoic acid

By formula: C6H10O3 + H2O = 2C3H6O2

Quantity Value Units Method Reference Comment
Δr-56.6 ± 0.4kJ/molCmConn, Kistiakowsky, et al., 1942liquid phase; Heat of hydrolysis at 303 K; ALS

Hydrogen + 2-Propenoic acid = Propanoic acid

By formula: H2 + C3H4O2 = C3H6O2

Quantity Value Units Method Reference Comment
Δr-127.0 ± 0.8kJ/molChydSkinner and Snelson, 1959liquid phase; solvent: Acetic acid; ALS

Methyl propionate + Water = Methyl Alcohol + Propanoic acid

By formula: C4H8O2 + H2O = CH4O + C3H6O2

Quantity Value Units Method Reference Comment
Δr-60.17 ± 0.92kJ/molEqkGuthrie and Cullimore, 1980liquid phase; ALS

NO3 anion + Water + Propanoic acid = C3H8NO6-

By formula: NO3- + H2O + C3H6O2 = C3H8NO6-

Quantity Value Units Method Reference Comment
Δr16.3 ± 0.84kJ/molIMREViidanoja, Reiner, et al., 2000gas phase; B

CO3 + Water + Propanoic acid = C4H8O6-

By formula: CO3 + H2O + C3H6O2 = C4H8O6-

Quantity Value Units Method Reference Comment
Δr16.7 ± 0.84kJ/molIMREViidanoja, Reiner, et al., 2000gas phase; B

NO3 anion + Propanoic acid = C3H6NO5-

By formula: NO3- + C3H6O2 = C3H6NO5-

Quantity Value Units Method Reference Comment
Δr50.21 ± 0.84kJ/molIMREViidanoja, Reiner, et al., 2000gas phase; B

Nitrogen oxide anion + Propanoic acid = C3H6NO4-

By formula: NO2- + C3H6O2 = C3H6NO4-

Quantity Value Units Method Reference Comment
Δr52.30 ± 0.84kJ/molIMREViidanoja, Reiner, et al., 2000gas phase; B

Sodium ion (1+) + Propanoic acid = (Sodium ion (1+) • Propanoic acid)

By formula: Na+ + C3H6O2 = (Na+ • C3H6O2)

Quantity Value Units Method Reference Comment
Δr118. ± 5.9kJ/molCIDTMoision and Armentrout, 2002RCD

Gas phase ion energetics data

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 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
LL - Sharon G. Lias and Joel F. Liebman
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

View reactions leading to C3H6O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)10.44 ± 0.06eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)797.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity766.2kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.4EIArakawa, 1990LL
10.51PITraeger, 1985LBLHLM
10.41EIHolmes, Fingas, et al., 1981LLK
10.41EIHolmes and Lossing, 1980LLK
10.525 ± 0.003PIWatanabe, Yokoyama, et al., 1974LLK
10.54PEWatanabe, Yokoyama, et al., 1973LLK
10.44 ± 0.03PEThomas, 1972LLK
10.24 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
10.51PEBenoit and Harrison, 1977Vertical value; LLK
10.72PEKimura, Katsumata, et al., 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHO2+12.6?EIArakawa, 1990LL
CHO2+12.84C2H5EIBernecker and Long, 1961RDSH
C2H5+12.4COOHEIArakawa, 1990LL
C2H5+12.90?EIBernecker and Long, 1961RDSH
C3H3O+13.1?EIArakawa, 1990LL
C3H4O+10.9H2OEIArakawa, 1990LL
C3H4O+11.57H2OEIBernecker and Long, 1961RDSH
C3H5O+11.2OHEIArakawa, 1990LL
C3H5O+11.00OHPITraeger, 1985LBLHLM
C3H5O+12.20OHEIBernecker and Long, 1961RDSH
C3H5O2+11.1HEIArakawa, 1990LL
C3H5O2+11.70HEIBernecker and Long, 1961RDSH

De-protonation reactions

EtCO2 anion + Hydrogen cation = Propanoic acid

By formula: C3H5O2- + H+ = C3H6O2

Quantity Value Units Method Reference Comment
Δr1454. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr1454. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr1424. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr1424. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

Lebedeva, 1964
Lebedeva, N.D., Heats of combustion of monocarboxylic acids, Russ. J. Phys. Chem. (Engl. Transl.), 1964, 38, 1435-1437. [all data]

Konicek and Wadso, 1970
Konicek, J.; Wadso, I., Enthalpies of vaporization of organic compounds. VII. Some carboxylic acids, Acta Chem. Scand., 1970, 24, 2612-26. [all data]

Schjanberg, 1935
Schjanberg, E., Die Verbrennungswarmen und die Refraktionsdaten einiger chlorsubstituierter Fettsauren und Ester., Z. Phys. Chem. Abt. A, 1935, 172, 197-233. [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]

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]

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]

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]

Essex and Sandholzer, 1938
Essex, H.; Sandholzer, M., The free energy of formation of ethyl propionate, J. Phys. Chem., 1938, 42, 317-333. [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]

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]

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

Viidanoja, Reiner, et al., 2000
Viidanoja, J.; Reiner, T.; Kiendler, A.; Grimm, F.; Arnold, F., Laboratory investigations of negative ion molecule reactions of propionic, butyric, glyoxylic, pyruvic, and pinonic acids, Int. J. Mass Spectrom., 2000, 194, 1, 53-68, https://doi.org/10.1016/S1387-3806(99)00172-4 . [all data]

Moision and Armentrout, 2002
Moision, R.M.; Armentrout, P.B., Experimental and Theoretical Dissection of Sodium Cation/Glycine Interactions, J. Phys. Chem A, 2002, 106, 43, 10350, https://doi.org/10.1021/jp0216373 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Arakawa, 1990
Arakawa, R., Time-resolved dissociation of ionized propanoic acid, Bull. Chem. Soc. Jpn., 1990, 61, 754. [all data]

Traeger, 1985
Traeger, J.C., Heat of formation for the propanoyl cation by photoionization mass spectrometry, Org. Mass Spectrom., 1985, 20, 223. [all data]

Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P., Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations, Can. J. Chem., 1981, 59, 80. [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]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Yamazaki, T.; Wakabayashi, H., UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 41. [all data]

Bernecker and Long, 1961
Bernecker, R.R.; Long, F., Some organic positive ions and their parent radicals and molecules, J. Phys. Chem., 1961, 65, 1565. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References