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2-Butenal

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Deltafgas-109.7 ± 2.4kJ/molCcbVan-chin-syan, Kochubei, et al., 1996ALS
Deltafgas-106.9kJ/molN/ATjebbes, 1960Value computed using «DELTA»fHliquid° value of -144.1±0.4 kj/mol from Tjebbes, 1960 and «DELTA»vapH° value of 37.2 kj/mol from Van-chin-syan, Kochubei, et al., 1996.; DRB
Deltafgas-100.5 ± 1.5kJ/molChydDolliver, Gresham, et al., 1938Heat of formation derived by Cox and Pilcher, 1970; ALS

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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
Deltafliquid-146.9 ± 2.4kJ/molCcbVan-chin-syan, Kochubei, et al., 1996 
Deltafliquid-144.1 ± 0.4kJ/molCcbTjebbes, 1960 
Deltafliquid-138.6 ± 1.9kJ/molChydDolliver, Gresham, et al., 1938Heat of formation derived by Cox and Pilcher, 1970
Quantity Value Units Method Reference Comment
Deltacliquid-2284.7 ± 2.3kJ/molCcbVan-chin-syan, Kochubei, et al., 1996Corresponding «DELTA»fliquid = -146.8 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-2287.4 ± 0.4kJ/molCcbTjebbes, 1960Corresponding «DELTA»fliquid = -144.1 kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, 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
Tboil375.50KN/AMarkovnik, Sachek, et al., 1979Uncertainty assigned by TRC = 0.02 K; TRC
Tboil375.5KN/AAnonymous, 1953Uncertainty assigned by TRC = 0.6 K; TRC
Tboil363.15KN/AMiller, Cook, et al., 1950Uncertainty assigned by TRC = 5. K; TRC
Tboil377.2KN/ATimmermans, 1922Uncertainty assigned by TRC = 0.3 K; TRC
Tboil375.3KN/ATimmermans, 1913Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus198.KN/AAnonymous, 1968Uncertainty assigned by TRC = 5. K; TRC
Tfus196.7KN/ATimmermans, 1922Uncertainty assigned by TRC = 0.5 K; TRC
Tfus199.15KN/ATimmermans, 1913Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Tc601.98KN/AGurarii, Kuleshov, et al., 1987Uncertainty assigned by TRC = 0.1 K; TRC
Quantity Value Units Method Reference Comment
Pc54.969barN/AGurarii, Kuleshov, et al., 1987Uncertainty assigned by TRC = 0.01 bar; TRC
Quantity Value Units Method Reference Comment
rhoc4.1803mol/lN/AGurarii, Kuleshov, et al., 1987Uncertainty assigned by TRC = 0.04 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap37.3 ± 0.4kJ/molCVan-chin-syan, Kochubei, et al., 1996ALS
Deltavap37.2kJ/molN/AVan-chin-syan, Kochubei, et al., 1996DRB
Deltavap37.3 ± 0.4kJ/molCVan-Chin-Syan, Kochubei, et al., 1996AC
Deltavap38. ± 0.8kJ/molEDolliver, Gresham, et al., 1938Heat of formation derived by Cox and Pilcher, 1970; ALS
Deltavap38.1kJ/molN/ADolliver, Gresham, et al., 1938DRB

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
38.8325.EBWiberg, Morgan, et al., 1994AC
35.1 ± 0.5332.N/ABaglay, Gurariy, et al., 1988Based on data from 288. - 376. K.; AC
36.8321.AStephenson and Malanowski, 1987Based on data from 306. - 376. K. See also Waradzin and Skubla, 1973 and Boublik, Fried, et al., 1984.; AC
37.3319.N/AMarkovnik, Sachek, et al., 1979Based on data from 304. - 377. K.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

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

C4H5O- + Hydrogen cation = 2-Butenal

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Deltar1484. ± 8.8kJ/molG+TSBartmess and Kiplinger, 1986gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1456. ± 8.4kJ/molIMREBartmess and Kiplinger, 1986gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B

(CAS Reg. No. 64724-02-3 bullet 42949672952-Butenal) + 2-Butenal = CAS Reg. No. 64724-02-3

By formula: (CAS Reg. No. 64724-02-3 bullet 4294967295C4H6O) + C4H6O = CAS Reg. No. 64724-02-3

Quantity Value Units Method Reference Comment
Deltar253. ± 9.2kJ/molN/AAlconcel, Deyerl, et al., 2001gas phase; B
Deltar256. ± 10.kJ/molTherZimmerman, Reed, et al., 1977gas phase; B

Hydrogen + 2-Butenal = Butanal

By formula: H2 + C4H6O = C4H8O

Quantity Value Units Method Reference Comment
Deltar-104.2 ± 0.42kJ/molChydDolliver, Gresham, et al., 1938gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -105.3 ± 0.4 kJ/mol; At 355°K; ALS

2-Butene, 1,1-dimethoxy- + Water = 2-Butenal + 2Methyl Alcohol

By formula: C6H12O2 + H2O = C4H6O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar15.3 ± 0.2kJ/molCmWiberg, Morgan, et al., 1994liquid phase; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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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Mass spectrum
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Additional Data

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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]

Anonymous, 1968
Anonymous, X., Chemicals and Plastics Physical Properties, 1968, Union Carbide Corp., product bulletin, 1968. [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]

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]

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]

Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References