2-Butenal

• Formula: C₄H₆O
• Molecular weight: 70.0898
• IUPAC Standard InChI: InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3 Copy

  
• IUPAC Standard InChIKey: MLUCVPSAIODCQM-UHFFFAOYSA-N Copy
• 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:
  • 2-Butenal, (E)-
  • 2-Butenal, (Z)-
• 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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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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
DRB - Donald R. Burgess, Jr.

Phase change 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:
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

Enthalpy of vaporization

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:
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)

Ionization energy determinations

De-protonation reactions

C₄H₅O^- +  =

By formula: C₄H₅O^- + H⁺ = C₄H₆O

Mass spectrum (electron ionization)

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Gas 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

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• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas 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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