2-Butenal
- Formula: C4H6O
- Molecular weight: 70.0898
- IUPAC Standard InChIKey: MLUCVPSAIODCQM-UHFFFAOYSA-N
- CAS Registry Number: 4170-30-3
- 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. - Stereoisomers:
- Other names: Crotonaldehyde; Crotonal; Crotonic aldehyde; Crotylaldehyde; β-Methylacrolein; Propylene aldehyde; Krotonaldehyd; Rcra waste number U053; UN 1143; But-2-enal; 1-Formylpropene; 2-Butenaldehyde; NSC 56354
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 | -35.11 ± 0.57 | kcal/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | |
ΔfH°liquid | -34.45 ± 0.09 | kcal/mol | Ccb | Tjebbes, 1960 | |
ΔfH°liquid | -33.13 ± 0.45 | kcal/mol | Chyd | Dolliver, Gresham, et al., 1938 | Heat of formation derived by Cox and Pilcher, 1970 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -546.06 ± 0.55 | kcal/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | Corresponding ΔfHºliquid = -35.09 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -546.71 ± 0.09 | kcal/mol | Ccb | Tjebbes, 1960 | Corresponding ΔfHºliquid = -34.44 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 375.50 | K | N/A | Markovnik, Sachek, et al., 1979 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tboil | 375.5 | K | N/A | Anonymous, 1953 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tboil | 363.15 | K | N/A | Miller, Cook, et al., 1950 | Uncertainty assigned by TRC = 5. K; TRC |
Tboil | 377.2 | K | N/A | Timmermans, 1922 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tboil | 375.3 | K | N/A | Timmermans, 1913 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 196.7 | K | N/A | Timmermans, 1922 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 199.15 | K | N/A | Timmermans, 1913 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 601.98 | K | N/A | Gurarii, Kuleshov, et al., 1987 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 54.250 | atm | N/A | Gurarii, Kuleshov, et al., 1987 | Uncertainty assigned by TRC = 0.01 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 4.1803 | mol/l | N/A | Gurarii, Kuleshov, et al., 1987 | Uncertainty assigned by TRC = 0.04 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.90 ± 0.1 | kcal/mol | C | Van-chin-syan, Kochubei, et al., 1996 | ALS |
ΔvapH° | 8.89 | kcal/mol | N/A | Van-chin-syan, Kochubei, et al., 1996 | DRB |
ΔvapH° | 8.91 ± 0.1 | kcal/mol | C | Van-Chin-Syan, Kochubei, et al., 1996 | AC |
ΔvapH° | 9.1 ± 0.2 | kcal/mol | E | Dolliver, Gresham, et al., 1938 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
ΔvapH° | 9.11 | kcal/mol | N/A | Dolliver, Gresham, et al., 1938 | DRB |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.27 | 325. | EB | Wiberg, Morgan, et al., 1994 | AC |
8.4 ± 0.1 | 332. | N/A | Baglay, Gurariy, et al., 1988 | Based on data from 288. to 376. K.; AC |
8.80 | 321. | A | Stephenson and Malanowski, 1987 | Based on data from 306. to 376. K. See also Waradzin and Skubla, 1973 and Boublik, Fried, et al., 1984.; AC |
8.91 | 319. | N/A | Markovnik, Sachek, et al., 1979 | Based on data from 304. to 377. K.; AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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
Data compiled as indicated in comments:
B - John E. Bartmess
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 C4H6O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 198.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 191.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.75 | PE | Masclet and Mouvier, 1978 | LLK |
9.73 ± 0.01 | PI | Watanabe, 1957 | RDSH |
9.86 ± 0.03 | PE | Klessinger and Gunkel, 1978 | Vertical value; LLK |
De-protonation reactions
C4H5O- + =
By formula: C4H5O- + H+ = C4H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 354.7 ± 2.1 | kcal/mol | G+TS | Bartmess and Kiplinger, 1986 | gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 348.1 ± 2.0 | kcal/mol | IMRE | Bartmess and Kiplinger, 1986 | gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118878 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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.
Van-chin-syan, Kochubei, et al., 1996
Van-chin-syan, Yu.Ya.; Kochubei, V.V.; Sergeev, V.V.; Raevskii, Yu.A.; Gerasimchuk, S.I.; Kotovich, Kh.Z.,
Thermodynamic properties of some acids and aldehydes of the acrylic series,
Sov. J. Chem. Phys. (Engl. Transl.), 1996, 70, 1789-1794, In original 1932. [all data]
Tjebbes, 1960
Tjebbes, J.,
Heats of combustion of butannal and some related compounds,
Acta Chem. Scand., 1960, 14, 180-188. [all data]
Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E.,
Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds,
J. Am. Chem. Soc., 1938, 60, 440-450. [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]
Markovnik, Sachek, et al., 1979
Markovnik, V.S.; Sachek, A.I.; Peshchenko, A.D.; Shvaro, O.V.; Andreevskii, D.N.; Olizarevich, N.M.,
Termodin. Org. Soedin., 1979, 107. [all data]
Anonymous, 1953
Anonymous, R.,
, Physical Properties of Chemical Substances, Dow Chemical Company, 1953. [all data]
Miller, Cook, et al., 1950
Miller, A.L.; Cook, N.C.; Whitmore, F.C.,
The Ketonic Decarboxylation Reaction: The Ketonic Decarboxylation of Trimethylacetic Acid and Isobutyric Acid,
J. Am. Chem. Soc., 1950, 72, 2732. [all data]
Timmermans, 1922
Timmermans, J.,
Investigation of the Freezing Point of Organic Substances VII,
Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]
Timmermans, 1913
Timmermans, J.,
Bull. Soc. Chim. Belg., 1913, 27, 334. [all data]
Gurarii, Kuleshov, et al., 1987
Gurarii, L.L.; Kuleshov, G.G.; Baglai, A.K.; Petrashkevich, R.I.,
Thermodynamic properties of 2-methoxypropene,
Khim.-Farm. Zh., 1987, 21, 247. [all data]
Van-Chin-Syan, Kochubei, et al., 1996
Van-Chin-Syan, Yu.Ya.; Kochubei, V.V.; Sergeev, V.V.; Raevskii, Yu.A.; Gerasimchuk, S.I.; Kotovich, Kh.Z.,
Thermodynamic properties of some acrylic-series acids and aldehydes,
Zh. Fiz. Khim., 1996, 70, 11, 1932. [all data]
Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H.,
Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria,
J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]
Baglay, Gurariy, et al., 1988
Baglay, A.K.; Gurariy, L.L.; Kuleshov, G.G.,
Physical properties of compounds used in vitamin synthesis,
J. Chem. Eng. Data, 1988, 33, 512-518. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Waradzin and Skubla, 1973
Waradzin, W.; Skubla, P.,
Chem. Prum., 1973, 23, 11, 556. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [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]
Masclet and Mouvier, 1978
Masclet, P.; Mouvier, G.,
Etude par spectrometrie photoelectronique d'aldehydes et de cetones ethyleniques conjugues,
J. Electron Spectrosc. Relat. Phenom., 1978, 14, 77. [all data]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [all data]
Klessinger and Gunkel, 1978
Klessinger, M.; Gunkel, E.,
The electronic structure of polyenes and unsaturated carbonyl compounds,
Tetrahedron, 1978, 34, 3591. [all data]
Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P.,
'Kinetic' vs. thermodynamic acidities of enones in the gas phase,
J. Org. Chem., 1986, 51, 2173. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point 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 ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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