Propanal, 2-methyl-
- Formula: C4H8O
- Molecular weight: 72.1057
- IUPAC Standard InChI: InChI=1S/C4H8O/c1-4(2)3-5/h3-4H,1-2H3
- IUPAC Standard InChIKey: AMIMRNSIRUDHCM-UHFFFAOYSA-N
- CAS Registry Number: 78-84-2
- 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: Isobutyraldehyde; α-Methylpropionaldehyde; Isobutanal; Isopropylaldehyde; Isopropylformaldehyde; 2-Methylpropanal; 2-Methylpropionaldehyde; iso-C3H7CHO; Isobutylaldehyde; Isobutyric aldehyde; 2-Methyl-1-propanal; Isobutyraldehyd; Propionaldehyde, 2-methyl-; Valine aldehyde; Isobutaldehyde; Isobutyryl aldehyde; Methyl propanal; NCI-C60968; UN 2045; Isobutyral; NSC 6739; 2-methylpropanal (isobutanal)
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -51.57 ± 0.37 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | ALS |
| ΔfH°gas | -51.72 | kcal/mol | N/A | Gubareva and Gerasimov, 1990 | Value computed using ΔfHliquid° value of -247.9±0.7 kj/mol from Gubareva and Gerasimov, 1990 and ΔvapH° value of 31.5 kj/mol from Connett, 1975.; DRB |
| ΔfH°gas | -51.55 ± 0.31 | kcal/mol | Eqk | Connett, 1975 | Heat of dehydrogenation; ALS |
| ΔfH°gas | -52.1 | kcal/mol | Ccb | Tjebbes, 1962 | ALS |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -59.11 ± 0.22 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | |
| ΔfH°liquid | -59.2 ± 0.2 | kcal/mol | Ccb | Gubareva and Gerasimov, 1990 | |
| ΔfH°liquid | -59.08 ± 0.31 | kcal/mol | Eqk | Connett, 1975 | Heat of dehydrogenation |
| ΔfH°liquid | -59.81 ± 0.18 | kcal/mol | Ccb | Tjebbes, 1962 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -590.2 ± 0.2 | kcal/mol | Ccb | Gubareva and Gerasimov, 1990 | Corresponding ΔfHºliquid = -59.27 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -589.67 ± 0.18 | kcal/mol | Ccb | Tjebbes, 1962 | Corresponding ΔfHºliquid = -59.79 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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
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
C4H7O- + =
By formula: C4H7O- + H+ = C4H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 366.8 ± 3.0 | kcal/mol | D-EA | Alconcel, Deyerl, et al., 2001 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 359.5 ± 3.1 | kcal/mol | H-TS | Alconcel, Deyerl, et al., 2001 | gas phase; B |
+
=
By formula: H2 + C4H8O = C4H10O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -20.88 ± 0.08 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
| ΔrH° | -16.3 ± 0.2 | kcal/mol | Eqk | Connett, 1975 | gas phase; Heat of dehydrogenation; ALS |
(CAS Reg. No. 35730-34-8 • 4294967295) +
= CAS Reg. No. 35730-34-8
By formula: (CAS Reg. No. 35730-34-8 • 4294967295C4H8O) + C4H8O = CAS Reg. No. 35730-34-8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 42.0 ± 2.2 | kcal/mol | N/A | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
=
+
By formula: C4H10O = H2 + C4H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 16.3 ± 0.2 | kcal/mol | Eqk | Connett, 1975 | gas phase; Heat of dehydrogenation; ALS |
+
= 2
+
By formula: C6H14O2 + H2O = 2CH4O + C4H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 8.698 ± 0.016 | kcal/mol | Eqk | Wiberg and Squires, 1981 | liquid phase; ALS |
+
=
By formula: H2O + C4H8O = C4H10O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -5.6 | kcal/mol | Eqk | Green and Hine, 1973 | liquid phase; ALS |
3 =
By formula: 3C4H8O = C12H24O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -6.804 | kcal/mol | Eqk | Ogorodnikov, Katsnel'son, et al., 1990 | liquid phase; PMR; ALS |
=
By formula: C4H8O = C4H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -20.60 | kcal/mol | Kin | Farberov, Bondarenko, et al., 1984 | liquid phase; ALS |
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.
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]
Gubareva and Gerasimov, 1990
Gubareva, A.I.; Gerasimov, P.A.,
Physicochemical properties of isobutyraldehyde,
J. Appl. Chem. USSR, 1990, 63, 844-846. [all data]
Connett, 1975
Connett, J.E.,
Chemical equilibria 6. Measurement of equilibrium constants for the dehydrogenation of 2-methylpropan-1-ol by a vapour-flow technique,
J. Chem. Thermodyn., 1975, 7, 1159-1162. [all data]
Tjebbes, 1962
Tjebbes, J.,
Heats of combustion of propanal and 2-methyl propanal,
Acta Chem. Scand., 1962, 16, 953-857. [all data]
Alconcel, Deyerl, et al., 2001
Alconcel, L.S.; Deyerl, H.J.; Continetti, R.E.,
Effects of alkyl substitution on the energetics of enolate anions and radicals,
J. Am. Chem. Soc., 2001, 123, 50, 12675-12681, https://doi.org/10.1021/ja0120431
. [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]
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]
Green and Hine, 1973
Green, L.R.; Hine, J.,
Isobutyraldehyde. The kinetics of acid- and base-catalyzed equilibrations in water,
J. Org. Chem., 1973, 38, 2801-28. [all data]
Ogorodnikov, Katsnel'son, et al., 1990
Ogorodnikov, A.L.; Katsnel'son, M.G.; Pinson, V.V.; Levin, Yu.V.,
Study of thermodynamic characteristics of a butyraldehyde-cyclic trimer system,
Zh. Prikl. Khim. (Leningrad), 1990, 63, 1340-1343. [all data]
Farberov, Bondarenko, et al., 1984
Farberov, M.I.; Bondarenko, A.V.; Tsilyurik, T.V.; Srednev, S.S.; Shutova, I.A.,
Epoxidation of isobutene with organic hydroperoxides, and certain syntheses on this basis,
J. Anal. Chem. USSR, 1984, 57, 1915-1919. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
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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