Butanoic acid

• Formula: C₄H₈O₂
• Molecular weight: 88.1051
• IUPAC Standard InChI: InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) Copy

  
• IUPAC Standard InChIKey: FERIUCNNQQJTOY-UHFFFAOYSA-N Copy
• CAS Registry Number: 107-92-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Butyric acid; n-Butanoic acid; n-Butyric acid; Ethylacetic acid; Propylformic acid; 1-Butyric acid; 1-Propanecarboxylic acid; n-C3H7COOH; Propanecarboxylic acid; Butanic acid; Buttersaeure; Kyselina maselna; UN 2820; 1-Butanoic acid; NSC 8415
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• Information on this page:
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Ion clustering data
  • IR Spectrum
  • Gas Chromatography
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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^- +  =

By formula: C₄H₇O₂^- + H⁺ = C₄H₈O₂

2 +  =

By formula: 2H₂ + C₄H₄O₂ = C₄H₈O₂

 +  +  = C₄H₁₀NO₆^-

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

CO₃ +  +  = C₅H₁₀O₆^-

By formula: CO₃ + H₂O + C₄H₈O₂ = C₅H₁₀O₆^-

 +  = C₄H₈NO₅^-

By formula: NO₃^- + C₄H₈O₂ = C₄H₈NO₅^-

 +  = C₄H₈NO₄^-

By formula: NO₂^- + C₄H₈O₂ = C₄H₈NO₄^-

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

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)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₇O₂^- +  =

By formula: C₄H₇O₂^- + H⁺ = C₄H₈O₂

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics 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.

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, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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