Propanal
- Formula: C3H6O
- Molecular weight: 58.0791
- IUPAC Standard InChIKey: NBBJYMSMWIIQGU-UHFFFAOYSA-N
- CAS Registry Number: 123-38-6
- 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: Propionaldehyde; Methylacetaldehyde; Propaldehyde; Propional; Propionic aldehyde; Propylaldehyde; Propylic aldehyde; C2H5CHO; n-Propionaldehyde; Propanalaldehyde; n-Propanal; Aldehyde propionique; Propanaldehyde; NCI-C61029; UN 1275; 1-Propanone; 1-Propanal; Proprionaldehyde; NSC 6493
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -188.7 ± 0.75 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | Heat of hydrogenation; ALS |
ΔfH°gas | -186.0 ± 1.5 | kJ/mol | Eqk | Connett, 1972 | At 473-524 K; ALS |
ΔfH°gas | -190.6 ± 0.88 | kJ/mol | Chyd | Buckley and Cox, 1967 | ALS |
ΔfH°gas | -192. | kJ/mol | Ccb | Tjebbes, 1962 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 304.4 ± 1.6 | J/mol*K | N/A | Connett, 1972 | This value was determined from the equilibrium measurements using improved experimental techniques. It agrees with values obtained by statistical mechanics. Earlier the value of 293.8(1.3) J/mol*K was obtained from equilibrium study [ Buckley E., 1967].; GT |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
77.50 | 273.15 | Chao J., 1986 | p=1 bar. The values of thermodynamic functions of [ Frankiss S.G., 1974] were adopted by [ Chao J., 1986]. [ Chermin, 1961, Vasilev I.A., 1966] calculated the thermodynamic functions of the cis isomer only.; GT |
80.73 ± 0.10 | 298.15 | ||
80.98 | 300. | ||
96.39 | 400. | ||
112.90 | 500. | ||
128.50 | 600. | ||
142.60 | 700. | ||
155.20 | 800. | ||
166.40 | 900. | ||
176.30 | 1000. | ||
185.10 | 1100. | ||
192.90 | 1200. | ||
199.80 | 1300. | ||
206.10 | 1400. | ||
211.70 | 1500. |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
84.53 | 325.04 | Counsell J.F., 1972 | GT |
88.39 | 350.07 | ||
92.22 | 374.50 |
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 |
---|---|---|---|---|---|
ΔfH°liquid | -218.3 ± 0.63 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | Heat of hydrogenation; ALS |
ΔfH°liquid | -215.7 ± 1.5 | kJ/mol | Eqk | Connett, 1972 | At 473-524 K; ALS |
ΔfH°liquid | -220.2 ± 0.96 | kJ/mol | Chyd | Buckley and Cox, 1967 | ALS |
ΔfH°liquid | -221.5 ± 0.75 | kJ/mol | Ccb | Tjebbes, 1962 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1816.5 ± 0.75 | kJ/mol | Ccb | Tjebbes, 1962 | Corresponding ΔfHºliquid = -221.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 212.9 | J/mol*K | N/A | Korkhov and Vasil'ev, 1977 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
159.1 | 298.15 | Korkhov and Vasil'ev, 1977 | T = 15 to 335 K.; DH |
134.7 | 298. | von Reis, 1881 | T = 288 to 328 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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
C3H5O- + =
By formula: C3H5O- + H+ = C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1528. ± 8.8 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1531. ± 10. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1501. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1504. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
By formula: C3H6O + H2 = C3H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -84.3 ± 0.4 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase; solvent: Triglyme; Heat of hydrogenation; ALS |
ΔrH° | -69.55 ± 0.76 | kJ/mol | Eqk | Connett, 1972 | gas phase; At 473-524 K; ALS |
ΔrH° | -65.77 ± 0.67 | kJ/mol | Chyd | Buckley and Cox, 1967 | gas phase; ALS |
By formula: NO- + C3H6O = (NO- • C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 159. | kJ/mol | ICR | Reents and Freiser, 1981 | gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978, ref. to PA(NH3)=872. kJ/mol; M |
(C3H7O- • 4294967295) +
= C3H7O-
By formula: (C3H7O- • 4294967295C3H6O) + C3H6O = C3H7O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 172. ± 9.2 | kJ/mol | N/A | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: Mg+ + C3H6O = (Mg+ • C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 270. ± 20. | kJ/mol | ICR | Operti, Tews, et al., 1988 | gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M |
By formula: C5H12O2 + H2O = C3H6O + 2CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 37.65 ± 0.071 | kJ/mol | Eqk | Wiberg and Squires, 1981 | liquid phase; ALS |
By formula: C3H6O = C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -98.7 | kJ/mol | Eqk | Polkovnikova and Lapiclus, 1974 | gas phase; At 300 K; ALS |
By formula: C3H6O = C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -32. | kJ/mol | Eqk | Polkovnikova and Lapiclus, 1974 | gas phase; At 300 K; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, 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 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
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 C3H6O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.96 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 786.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 754.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.000999 ± 0.000087 | Hammer, Diri, et al., 2003 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.96 | PI | Traeger, 1985 | LBLHLM |
9.96 | PI | Traeger, 1985, 2 | LBLHLM |
9.82 ± 0.14 | EI | El-Sherbini, Allam, et al., 1981 | LLK |
9.95 | PI | Staley, Wieting, et al., 1977 | LLK |
9.953 ± 0.005 | PE | Hernandez, Masclet, et al., 1977 | LLK |
9.99 | PE | Tam, Yee, et al., 1974 | LLK |
9.97 ± 0.01 | PE | Cocksey, Eland, et al., 1971 | LLK |
9.94 | PE | Dewar and Worley, 1969 | RDSH |
9.98 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.96 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
9.85 | PE | Kimura, Katsumata, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 11.79 | C2H5 | PI | Traeger, 1985 | LBLHLM |
C2H3O+ | 12.3 ± 0.05 | CH3 | EI | Burgers and Holmes, 1982 | LBLHLM |
C2H3O+ | 10.79 | CH3 | PI | Staley, Wieting, et al., 1977 | LLK |
C3H5O+ | 10.18 | H | PI | Traeger, 1985, 2 | LBLHLM |
De-protonation reactions
C3H5O- + =
By formula: C3H5O- + H+ = C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1528. ± 8.8 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1531. ± 10. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1501. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1504. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, 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.
Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M.,
Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups,
J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]
Connett, 1972
Connett, J.E.,
Chemical equilibria. 5. Measurement of equilibrium constants for the dehydrogenation of propanol by a vapour flow technique,
J. Chem. Thermodyn., 1972, 4, 233-237. [all data]
Buckley and Cox, 1967
Buckley, E.; Cox, J.D.,
Chemical equilibria. Part 2.-Dehydrogenation of propanol and butanol,
Trans. Faraday Soc., 1967, 63, 895-901. [all data]
Tjebbes, 1962
Tjebbes, J.,
Heats of combustion of propanal and 2-methyl propanal,
Acta Chem. Scand., 1962, 16, 953-857. [all data]
Buckley E., 1967
Buckley E.,
Chemical equilibria. Part 2. Dehydrogenation of propanol and butanol,
Trans. Faraday Soc., 1967, 63, 895-901. [all data]
Chao J., 1986
Chao J.,
Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties,
J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]
Frankiss S.G., 1974
Frankiss S.G.,
Thermodynamic properties of organic oxygen compounds. Part 36. Chemical thermodynamic properties of propanal,
J. Chem. Soc. Faraday Trans. 2, 1974, 70, 1516-1521. [all data]
Chermin, 1961
Chermin, H.A.G.,
Thermo data for petrochemicals. Part 27: Gaseous normal aldehydes. The important thermo properties are presented for all the gaseous normal aldehydes from formaldehyde through decaldehyde,
Pet. Refin., 1961, 40, 181-184. [all data]
Vasilev I.A., 1966
Vasilev I.A.,
Thermodynamic functions of propionaldehyde,
Zh. Fiz. Khim., 1966, 40, 842-847. [all data]
Counsell J.F., 1972
Counsell J.F.,
Thermodynamic properties of organic oxygen compounds. 30. Vapor heat capacity and enthalpy of vaporization of propanal,
J. Chem. Thermodyn., 1972, 4, 915-917. [all data]
Korkhov and Vasil'ev, 1977
Korkhov, A.D.; Vasil'ev, I.A.,
Heat capacity and thermodynamic functions of propanal at low temperatures,
Termodin. Org. Soedin., 1977, (6), 34-37. [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]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [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]
Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S.,
Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes,
J. Am. Chem. Soc., 1981, 103, 2791. [all data]
Farid and McMahon, 1978
Farid, R.; McMahon, T.B.,
Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy,
Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0
. [all data]
Operti, Tews, et al., 1988
Operti, L.; Tews, E.C.; Freiser, B.S.,
Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques,
J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020
. [all data]
Wiberg and Squires, 1981
Wiberg, K.B.; Squires, R.R.,
Thermochemical studies of carbonyl reactions. 2. Steric effects in acetal and ketal hydrolysis,
J. Am. Chem. Soc., 1981, 103, 4473-4478. [all data]
Polkovnikova and Lapiclus, 1974
Polkovnikova, A.G.; Lapiclus, V.L.,
Calculation of the equilibrium and heat of isomerization of propylene oxide on a lithium phosphate catalyst,
Neftekhimiya, 1974, 14, 113-115. [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]
Hammer, Diri, et al., 2003
Hammer, N.I.; Diri, K.; Jordan, K.D.; Desfrancois, C.; Compton, R.N.,
Dipole-bound anions of carbonyl, nitrile, and sulfoxide containing molecules,
J. Chem. Phys., 2003, 119, 7, 3650-3660, https://doi.org/10.1063/1.1590959
. [all data]
Traeger, 1985
Traeger, J.C.,
Heat of formation for the formyl cation by photoionization mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1985, 66, 271. [all data]
Traeger, 1985, 2
Traeger, J.C.,
Heat of formation for the propanoyl cation by photoionization mass spectrometry,
Org. Mass Spectrom., 1985, 20, 223. [all data]
El-Sherbini, Allam, et al., 1981
El-Sherbini, T.M.; Allam, S.H.; Migahed, M.D.; Dawoud, A.M.,
Mass spectrometric investigation of aliphatic aldehydes,
Z. Naturforsch. A:, 1981, 36, 1334. [all data]
Staley, Wieting, et al., 1977
Staley, R.H.; Wieting, R.D.; Beauchamp, J.L.,
Carbenium ion stabilities in the gas phase and solution. An ion cyclotron resonance study of bromide transfer reactions involving alkali ions, alkyl carbenium ions, acyl cations and cyclic halonium ions,
J. Am. Chem. Soc., 1977, 99, 5964. [all data]
Hernandez, Masclet, et al., 1977
Hernandez, R.; Masclet, P.; Mouvier, G.,
Spectroscopie de photoelectrons d'aldehydes et de cetones aliphatiques,
J. Electron Spectrosc. Relat. Phenom., 1977, 10, 333. [all data]
Tam, Yee, et al., 1974
Tam, W.-C.; Yee, D.; Brion, C.E.,
Photoelectron spectra of some aldehydes and ketones,
J. Electron Spectrosc. Relat. Phenom., 1974, 4, 77. [all data]
Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J.,
The effect of alkyl substitution on ionisation potential,
J. Chem. Soc., 1971, (B), 790. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [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]
Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L.,
Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks,
Org. Mass Spectrom., 1982, 17, 123. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy S°gas Entropy of gas at standard conditions 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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