2-Propenal

Formula: C₃H₄O
Molecular weight: 56.0633
IUPAC Standard InChI: InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2
IUPAC Standard InChIKey: HGINCPLSRVDWNT-UHFFFAOYSA-N
CAS Registry Number: 107-02-8
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: Acrolein; Acrylaldehyde; Acrylic Aldehyde; Allyl aldehyde; Aqualin; NSC 8819; Prop-2-En-1-al; Propenal; 2-Propen-1-one; CH2=CHCHO; Acraldehyde; Acraldehydeacroleina; Acroleine; Acrylaldehyd; Akrolein; Akroleina; Aldehyde acrylique; Aldeide acrilica; Aqualine; Crolean; Ethylene aldehyde; Magnacide H; Propylene aldehyde; Slimicide; Acroleina; Magnacide; Rcra waste number P003; UN 1092; 2-Propenaldehyde; (E)-2-propenal
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Gas phase thermochemistry data

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
35.19	50.	Thermodynamics Research Center, 1997	p=1 bar. Selected values agree with results of statistical calculation [ Compton D.A.C., 1977] within 0.1-1.4 J/molK. Thermodynamic functions calculated by [ Anjaneyulu Y., 1988] are larger than selected ones at high temperatures (up to 6.6 J/molK in S(1500 K) and 2.8 J/mol*K in Cp(1500 K)).
40.82	100.
47.03	150.
54.57	200.
66.98	273.15
71.28	298.15
71.59	300.
87.72	400.
101.33	500.
112.42	600.
121.45	700.
128.9	800.
135.0	900.
140.2	1000.
144.6	1100.
148.3	1200.
151.4	1300.
154.1	1400.
156.4	1500.

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1632.	kJ/mol	Ccb	Moureu and Boutaric, 1920	Corresponding Δ_fHº_liquid = -120. kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Quantity	Value	Units	Method	Reference	Comment
T_boil	330. ± 30.	K	AVG	N/A	Average of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	185.5	K	N/A	Timmermans, 1922	Uncertainty assigned by TRC = 0.4 K; TRC
T_fus	184.65	K	N/A	Moureu, Boutaric, et al., 1920	Uncertainty assigned by TRC = 1. K; TRC

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
32.3	265.	A	Stephenson and Malanowski, 1987	Based on data from 250. to 306. K.; AC
33.5	223.	A	Stephenson and Malanowski, 1987	Based on data from 208. to 326. K. See also Stull, 1947.; AC
30.9	314.	N/A	Markovnik, Sachek, et al., 1979	Based on data from 304. to 325. K.; AC

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
208.7 to 325.7	4.11586	1167.888	-41.56	Stull, 1947	Coefficents calculated by NIST from author's data.

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:

Gas phase ion energetics data

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Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
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 C₃H₄O⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	10.11 ± 0.01	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	797.0	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	765.1	kJ/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.10	CI	Ohno, Okamura, et al., 1995	LL
10.1	PE	Bock, Mohmand, et al., 1982	LBLHLM
10.1	PE	Von Niessen, Bieri, et al., 1980	LLK
10.11	PE	Van Dam and Oskam, 1978	LLK
10.11	PE	Masclet and Mouvier, 1978	LLK
10.13	PE	Katrib and Rabalais, 1973	LLK
10.14 ± 0.06	EI	Reed and Thornley, 1958	RDSH
10.10 ± 0.01	PI	Watanabe, 1957	RDSH
10.103 ± 0.006	S	Walsh, 1945	RDSH
10.15	PE	Schweig, Vermeer, et al., 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CHO⁺	13.30 ± 0.10	C₂H₃	EI	Haney and Franklin, 1969	RDSH
C₂H₃⁺	13.64	CHO?	EI	Haney and Franklin, 1969	RDSH

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Notes

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Compton D.A.C., 1977
Compton D.A.C., Values for the gas-phase thermodynamic functions of conjugated compounds existing as a mixture of conformers, J. Chem. Soc. Perkin Trans. 2, 1977, 1307-1311. [all data]

Anjaneyulu Y., 1988
Anjaneyulu Y., Thermodynamic functions of some acryl derivatives, J. Indian Chem. Soc., 1988, 65, 400-403. [all data]

Moureu and Boutaric, 1920
Moureu, C.; Boutaric, A., Some physico-chemical constants of acrylic acid, J. Chim. Phys., 1920, 18, 348-352. [all data]

Timmermans, 1922
Timmermans, J., Investigation of the Freezing Point of Organic Substances VII, Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]

Moureu, Boutaric, et al., 1920
Moureu, C.; Boutaric, A.; Dufraisse, C., Some Physical Chemical Constants of Acrolein, J. Chim. Phys. Phys.-Chim. Biol., 1920, 18, 333-47. [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

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]

Ohno, Okamura, et al., 1995
Ohno, K.; Okamura, K.; Yamakado, H.; Hoshino, S.; Takami, T.; Yamauchi, M., Penning ionization of HCHO, CH₂CH₂, and CH₂CHCHO by collision with He*(2 3S) metastable atoms, J. Phys. Chem., 1995, 99, 14247. [all data]

Bock, Mohmand, et al., 1982
Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A., Thioacrolein: Das stabilste C₃H₄S-Isomers und sein PE-spektroskopischer Nachweis in der gasphase, Chem. Ber., 1982, 115, 1339. [all data]

Von Niessen, Bieri, et al., 1980
Von Niessen, W.; Bieri, G.; Asbrink, L., 30.4 nm He(II) photoelectron spectra of organic molecules. Part III. Oxo-compounds (C,H,O), J. Electron Spectrosc. Relat. Phenom., 1980, 21, 175. [all data]

Van Dam and Oskam, 1978
Van Dam, H.; Oskam, A., He(I) and He(II) photoelectron spectra of some substituted ethylenes, J. Electron Spectrosc. Relat. Phenom., 1978, 13, 273. [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]

Katrib and Rabalais, 1973
Katrib, A.; Rabalais, J.W., Electronic interaction between the vinyl group and its substituents, J. Phys. Chem., 1973, 77, 2358. [all data]

Reed and Thornley, 1958
Reed, R.I.; Thornley, M.B., Studies in electron impact methods. Part 5. Acetaldehyde, acrolein, benzaldehyde, and propionaldehyde, J. Chem. Soc. Faraday Trans., 1958, 54, 949. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Walsh, 1945
Walsh, A.D., The absorption spectra of acrolein, crotonaldehyde and mesityl oxide in the vacuum ultra-violet, J. Chem. Soc. Faraday Trans., 1945, 41, 498. [all data]

Schweig, Vermeer, et al., 1974
Schweig, A.; Vermeer, H.; Weidner, U., A photoelectron spectroscopic study of keto-enol tautomerism in acetylacetones - a new application of photoelectron spectroscopy, Chem. Phys. Lett., 1974, 26, 229. [all data]

Haney and Franklin, 1969
Haney, M.A.; Franklin, J.L., Excess energies in mass spectra of some oxygen-containing organic compounds, J. Chem. Soc. Faraday Trans., 1969, 65, 1794. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
IE (evaluated)	Recommended ionization energy
T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_vapH	Enthalpy of vaporization

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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