Propanoic acid
- Formula: C3H6O2
- Molecular weight: 74.0785
- IUPAC Standard InChIKey: XBDQKXXYIPTUBI-UHFFFAOYSA-N
- CAS Registry Number: 79-09-4
- 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: Propionic acid; Carboxyethane; Ethanecarboxylic acid; Ethylformic acid; Luprisol; Luprosil; Metacetonic acid; Prozoin; Pseudoacetic acid; C2H5COOH; Methylacetic acid; Acide propionique; Kyselina propionova; Propionic acid grain preserver; Sentry grain preserver; Tenox P grain preservative; UN 1848; MonoProp; Antischim B; Propkorn; Propcorn; n-Propionic acid
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Gas phase thermochemistry data
Go To: Top, Condensed 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 compiled by: Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -108.9 ± 0.48 | kcal/mol | N/A | Lebedeva, 1964 | Value 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. |
ΔfH°gas | -108.9 ± 0.48 | kcal/mol | Ccb | Lebedeva, 1964 | Value computed using ΔfHliquid° from Lebedeva, 1964 and ΔvapH° value of 13. kcal/mol from Konicek and Wadso, 1970. |
ΔfH°gas | -108.7 ± 0.76 | kcal/mol | Ccb | Schjanberg, 1935 | Value computed using ΔfHliquid° from Schjanberg, 1935 and ΔvapH° value of 13. kcal/mol from Konicek and Wadso, 1970. estimated uncertainty |
Condensed phase thermochemistry 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 compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -122.08 ± 0.03 | kcal/mol | Ccb | Lebedeva, 1964 | ALS |
ΔfH°liquid | -121.9 ± 0.60 | kcal/mol | Ccb | Schjanberg, 1935 | estimated uncertainty; DRB |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -365.03 ± 0.03 | kcal/mol | Ccb | Lebedeva, 1964 | Corresponding ΔfHºliquid = -122.07 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -365.2 | kcal/mol | Ccb | Schjanberg, 1935 | Corresponding ΔfHºliquid = -121.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 45.65 | cal/mol*K | N/A | Martin and Andon, 1982 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
37.91 | 298.15 | Biros, Sikora, et al., 1982 | T = 270 to 370 K. Equation only. Cp = 129.7 - 0.1263 T + 0.0007486 T2 J/mol*K.; DH |
36.52 | 298.15 | Martin and Andon, 1982 | T = 13 to 450 K. Data also given by equation.; DH |
36.95 | 333.15 | Woycicka and Kalinowska, 1978 | DH |
36.1 | 298.15 | Konicek and Wadso, 1971 | DH |
38.10 | 289. | Radulescu and Jula, 1934 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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
By formula: C3H5O2- + H+ = C3H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 347.4 ± 2.2 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 347.4 ± 2.9 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 340.4 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 340.3 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
By formula: I- + C3H6O2 = (I- • C3H6O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 16.6 ± 1.0 | kcal/mol | TDAs | Caldwell and Kebarle, 1984 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 10.5 ± 1.0 | kcal/mol | TDAs | Caldwell and Kebarle, 1984 | gas phase; B |
+
= C9H11O2S-
By formula: C6H5S- + C3H6O2 = C9H11O2S-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.00 ± 0.40 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 12.4 ± 1.3 | kcal/mol | TDAs | Sieck and Meot-ner, 1989 | gas phase; B |
By formula: C2H6O + C3H6O2 = C5H10O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -5.40 ± 0.10 | kcal/mol | Eqk | Essex and Sandholzer, 1938 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -5.627 kcal/mol; ALS |
By formula: C6H10O3 + H2O = 2C3H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -13.5 ± 0.1 | kcal/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydrolysis at 303 K; ALS |
By formula: H2 + C3H4O2 = C3H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -30.4 ± 0.2 | kcal/mol | Chyd | Skinner and Snelson, 1959 | liquid phase; solvent: Acetic acid; ALS |
By formula: C4H8O2 + H2O = CH4O + C3H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -14.38 ± 0.22 | kcal/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase; ALS |
+
+
= C3H8NO6-
By formula: NO3- + H2O + C3H6O2 = C3H8NO6-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 3.90 ± 0.20 | kcal/mol | IMRE | Viidanoja, Reiner, et al., 2000 | gas phase; B |
By formula: CO3 + H2O + C3H6O2 = C4H8O6-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 4.00 ± 0.20 | kcal/mol | IMRE | Viidanoja, Reiner, et al., 2000 | gas phase; B |
+
= C3H6NO5-
By formula: NO3- + C3H6O2 = C3H6NO5-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 12.00 ± 0.20 | kcal/mol | IMRE | Viidanoja, Reiner, et al., 2000 | gas phase; B |
+
= C3H6NO4-
By formula: NO2- + C3H6O2 = C3H6NO4-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 12.50 ± 0.20 | kcal/mol | IMRE | Viidanoja, Reiner, et al., 2000 | gas phase; B |
By formula: Na+ + C3H6O2 = (Na+ • C3H6O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 28.2 ± 1.4 | kcal/mol | CIDT | Moision and Armentrout, 2002 | RCD |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]
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]
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]
Woycicka and Kalinowska, 1978
Woycicka, M.; Kalinowska, B.,
Excess entahlpy and heat capacities of diluted propionic acid solutions in n-heptane, Bull. Acad. Pol. Sci.,
Ser. Sci. Chim., 1978, 26, 371-375. [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]
Radulescu and Jula, 1934
Radulescu, D.; Jula, O.,
Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen,
Z. Phys. Chem., 1934, B26, 390-393. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas 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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