Butanoic acid

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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 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
Δfliquid-127.61 ± 0.14kcal/molCcbLebedeva, 1964ALS
Quantity Value Units Method Reference Comment
Δcliquid-521.87 ± 0.14kcal/molCcbLebedeva, 1964Corresponding Δfliquid = -127.59 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid53.85cal/mol*KN/AMartin and Andon, 1982DH
liquid54.11cal/mol*KN/AParks, Kelley, et al., 1929Extrapolation below 90 K, 53.6 J/mol*K. Revision of previous data.; DH
liquid60.99cal/mol*KN/AParks and Anderson, 1926Extrapolation below 90 K, 82.42 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
42.47298.15Martin and Andon, 1982T = 13 to 450 K. Data also given by equation.; DH
42.5298.15Konicek and Wadso, 1971DH
42.09290.7Parks and Anderson, 1926T = 89 to 291292 to 448 K. Value is unsmoothed experimental datum.; DH
42.09298.von Reis, 1881T = 292 to 448 K.; DH

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

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

C4H7O2- + Hydrogen cation = Butanoic acid

By formula: C4H7O2- + H+ = C4H8O2

Quantity Value Units Method Reference Comment
Δr346.8 ± 2.0kcal/molTDEqNorrman and McMahon, 1999gas phase; B
Δr346.5 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr346.5 ± 2.2kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr339.5 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr339.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

2Hydrogen + 3-Butynoic acid = Butanoic acid

By formula: 2H2 + C4H4O2 = C4H8O2

Quantity Value Units Method Reference Comment
Δr-69.80 ± 0.20kcal/molChydFlitcroft and Skinner, 1958solid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -72.4 ± 1.1 kcal/mol; ALS

NO3 anion + Water + Butanoic acid = C4H10NO6-

By formula: NO3- + H2O + C4H8O2 = C4H10NO6-

Quantity Value Units Method Reference Comment
Δr3.80 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 2000gas phase; B

CO3 + Water + Butanoic acid = C5H10O6-

By formula: CO3 + H2O + C4H8O2 = C5H10O6-

Quantity Value Units Method Reference Comment
Δr3.60 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 2000gas phase; B

NO3 anion + Butanoic acid = C4H8NO5-

By formula: NO3- + C4H8O2 = C4H8NO5-

Quantity Value Units Method Reference Comment
Δr12.80 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 2000gas phase; B

Nitrogen oxide anion + Butanoic acid = C4H8NO4-

By formula: NO2- + C4H8O2 = C4H8NO4-

Quantity Value Units Method Reference Comment
Δr13.30 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 2000gas phase; B

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
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 C4H8O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)10.17 ± 0.05eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
10.17 ± 0.05PIPECOButler, Fraser-Monteiro, et al., 1982LBLHLM
10.24EIHolmes, Fingas, et al., 1981LLK
10.24EIHolmes and Lossing, 1980LLK
10.46PEWatanabe, Yokoyama, et al., 1973LLK
10.16 ± 0.05PIWatanabe, Nakayama, et al., 1962RDSH
10.38PEBenoit and Harrison, 1977Vertical value; LLK
10.22PESustmann and Trill, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H4+11.5 ± 0.1C2H4O2PIPECOButler, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C2H4O2+10.42 ± 0.05C2H4PIPECOButler, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C2H4O2+10.60C2H4EIHolmes and Lossing, 1980LLK
C2H5+11.6 ± 0.1C2H3O2PIPECOButler, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C2H402+10.60 ± 0.05C2H4EIHolmes and Lossing, 1980, 2LLK
C3H5O2+10.5 ± 0.1CH3PIPECOButler, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C3H6+11.4 ± 0.1CH2O2PIPECOButler, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C3H7+10.96 ± 0.05COOHPIPECOButler, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C4H7O+11.8 ± 0.1OHPIPECOButler, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM

De-protonation reactions

C4H7O2- + Hydrogen cation = Butanoic acid

By formula: C4H7O2- + H+ = C4H8O2

Quantity Value Units Method Reference Comment
Δr346.8 ± 2.0kcal/molTDEqNorrman and McMahon, 1999gas phase; B
Δr346.5 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr346.5 ± 2.2kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr339.5 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr339.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

References

Go To: Top, Condensed 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]

Martin and Andon, 1982
Martin, J.F.; Andon, R.J.L., Thermodynamic properties of organic oxygen compounds. Part LII. Molar heat capacity of ethanoic, propanoic, and butanoic acids, J. Chem. Thermodynam., 1982, 14, 679-688. [all data]

Parks, Kelley, et al., 1929
Parks, G.S.; Kelley, K.K.; Huffman, H.M., Thermal data on organic compounds. V. A revision of the entropies and free energies of nineteen organic compounds, J. Am. Chem. Soc., 1929, 51, 1969-1973. [all data]

Parks and Anderson, 1926
Parks, G.S.; Anderson, C.T., Thermal data on organic compounds. III. The heat capacities, entropies and free energies of tertiary butyl alcohol, mannitol, erythritol and normal butyric acid, J. Am. Chem. Soc., 1926, 48, 1506-1512. [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]

Norrman and McMahon, 1999
Norrman, K.; McMahon, T.B., Intramolecular solvation of carboxylate anions in the gas phase, J. Phys. Chem. A, 1999, 103, 35, 7008-7016, https://doi.org/10.1021/jp9908202 . [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]

Flitcroft and Skinner, 1958
Flitcroft, T.L.; Skinner, H.A., Heats of hydrogenation Part 2.-Acetylene derivatives, Trans. Faraday Soc., 1958, 54, 47-53. [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]

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]

Butler, Fraser-Monteiro, et al., 1982
Butler, J.J.; Fraser-Monteiro, M.L.; Fraser-Monteiro, L.; Baer, T.; Hass, J.R., Thermochemistry and dissociation dynamics of state-selected C4H8O2+ Ions. 2. Butanoic acid, J. Phys. Chem., 1982, 86, 747. [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., 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]

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]

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 and Lossing, 1980, 2
Holmes, J.L.; Lossing, F.P., Thermochemistry and unimolecular reactions of ionized acetic acid and its enol in the gas phase., J. Am. Chem. Soc., 1980, 102, 3732. [all data]


Notes

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