Butanoic acid
- Formula: C4H8O2
- Molecular weight: 88.1051
- IUPAC Standard InChIKey: FERIUCNNQQJTOY-UHFFFAOYSA-N
- 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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Condensed phase thermochemistry data
Go To: Top, 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:
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 | -127.61 ± 0.14 | kcal/mol | Ccb | Lebedeva, 1964 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -521.87 ± 0.14 | kcal/mol | Ccb | Lebedeva, 1964 | Corresponding ΔfHºliquid = -127.59 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 53.85 | cal/mol*K | N/A | Martin and Andon, 1982 | DH |
S°liquid | 54.11 | cal/mol*K | N/A | Parks, Kelley, et al., 1929 | Extrapolation below 90 K, 53.6 J/mol*K. Revision of previous data.; DH |
S°liquid | 60.99 | cal/mol*K | N/A | Parks and Anderson, 1926 | Extrapolation below 90 K, 82.42 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
42.47 | 298.15 | Martin and Andon, 1982 | T = 13 to 450 K. Data also given by equation.; DH |
42.5 | 298.15 | Konicek and Wadso, 1971 | DH |
42.09 | 290.7 | Parks and Anderson, 1926 | T = 89 to 291292 to 448 K. Value is unsmoothed experimental datum.; DH |
42.09 | 298. | von Reis, 1881 | T = 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- + =
By formula: C4H7O2- + H+ = C4H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 346.8 ± 2.0 | kcal/mol | TDEq | Norrman and McMahon, 1999 | gas phase; B |
ΔrH° | 346.5 ± 2.2 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 346.5 ± 2.2 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 339.5 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 339.5 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
By formula: 2H2 + C4H4O2 = C4H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -69.80 ± 0.20 | kcal/mol | Chyd | Flitcroft and Skinner, 1958 | solid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -72.4 ± 1.1 kcal/mol; ALS |
+
+
= C4H10NO6-
By formula: NO3- + H2O + C4H8O2 = C4H10NO6-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 3.80 ± 0.20 | kcal/mol | IMRE | Viidanoja, Reiner, et al., 2000 | gas phase; B |
By formula: CO3 + H2O + C4H8O2 = C5H10O6-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 3.60 ± 0.20 | kcal/mol | IMRE | Viidanoja, Reiner, et al., 2000 | gas phase; B |
+
= C4H8NO5-
By formula: NO3- + C4H8O2 = C4H8NO5-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 12.80 ± 0.20 | kcal/mol | IMRE | Viidanoja, Reiner, et al., 2000 | gas phase; B |
+
= C4H8NO4-
By formula: NO2- + C4H8O2 = C4H8NO4-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 13.30 ± 0.20 | kcal/mol | IMRE | Viidanoja, Reiner, et al., 2000 | gas 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 ± 0.05 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.17 ± 0.05 | PIPECO | Butler, Fraser-Monteiro, et al., 1982 | LBLHLM |
10.24 | EI | Holmes, Fingas, et al., 1981 | LLK |
10.24 | EI | Holmes and Lossing, 1980 | LLK |
10.46 | PE | Watanabe, Yokoyama, et al., 1973 | LLK |
10.16 ± 0.05 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
10.38 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
10.22 | PE | Sustmann and Trill, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4+ | 11.5 ± 0.1 | C2H4O2 | PIPECO | Butler, Fraser-Monteiro, et al., 1982 | T = 298K; LBLHLM |
C2H4O2+ | 10.42 ± 0.05 | C2H4 | PIPECO | Butler, Fraser-Monteiro, et al., 1982 | T = 298K; LBLHLM |
C2H4O2+ | 10.60 | C2H4 | EI | Holmes and Lossing, 1980 | LLK |
C2H5+ | 11.6 ± 0.1 | C2H3O2 | PIPECO | Butler, Fraser-Monteiro, et al., 1982 | T = 298K; LBLHLM |
C2H402+ | 10.60 ± 0.05 | C2H4 | EI | Holmes and Lossing, 1980, 2 | LLK |
C3H5O2+ | 10.5 ± 0.1 | CH3 | PIPECO | Butler, Fraser-Monteiro, et al., 1982 | T = 298K; LBLHLM |
C3H6+ | 11.4 ± 0.1 | CH2O2 | PIPECO | Butler, Fraser-Monteiro, et al., 1982 | T = 298K; LBLHLM |
C3H7+ | 10.96 ± 0.05 | COOH | PIPECO | Butler, Fraser-Monteiro, et al., 1982 | T = 298K; LBLHLM |
C4H7O+ | 11.8 ± 0.1 | OH | PIPECO | Butler, Fraser-Monteiro, et al., 1982 | T = 298K; LBLHLM |
De-protonation reactions
C4H7O2- + =
By formula: C4H7O2- + H+ = C4H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 346.8 ± 2.0 | kcal/mol | TDEq | Norrman and McMahon, 1999 | gas phase; B |
ΔrH° | 346.5 ± 2.2 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 346.5 ± 2.2 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 339.5 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 339.5 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas 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
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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