2-Butenoic acid, (E)-
- Formula: C4H6O2
- Molecular weight: 86.0892
- IUPAC Standard InChIKey: LDHQCZJRKDOVOX-NSCUHMNNSA-N
- CAS Registry Number: 107-93-7
- 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: Crotonic acid, (E)-; (E)-Crotonic acid; (E)-2-Butenoic acid; trans-Crotonic Acid; trans-2-Butenoic Acid; (E)-CH3CH=CHCOOH; α-butenoic acid, trans; α-crotonic acid, trans; Ethylideneacetic acid, E; β-methylacrylic acid, trans; 3-Methylacrylic acid, trans; Crotonic acid, trans; β-Methacrylic acid, trans; 2-Butenoic acid, (2E)-; NSC 8751; Crotonic acid
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible 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: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.6 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. |
55.9 | 100. | ||
70.4 | 150. | ||
83.5 | 200. | ||
102.1 | 273.15 | ||
108.3 | 298.15 | ||
108.8 | 300. | ||
132.5 | 400. | ||
152.8 | 500. | ||
169.4 | 600. | ||
183.1 | 700. | ||
194.6 | 800. | ||
204.4 | 900. | ||
212.8 | 1000. | ||
220.0 | 1100. | ||
226.2 | 1200. | ||
231.6 | 1300. | ||
236.2 | 1400. | ||
240.3 | 1500. |
Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -2085. | kJ/mol | Ccb | Clopatt, 1932 | Corresponding ΔfHºliquid = -346. kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -2000. | kJ/mol | Ccb | Bruylants and Stassens, 1921 | Corresponding ΔfHºliquid = -431.4 kJ/mol (simple calculation by NIST; no Washburn corrections) |
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:
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 |
---|---|---|---|---|---|
Tboil | 453.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 458.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 344.7 | K | N/A | Gladstone, 1959 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 344.8 | K | N/A | Anonymous, 1955 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 344.6 | K | N/A | Lynn, 1925 | Uncertainty assigned by TRC = 0.4 K; as quoted in 1928 skasax 0; TRC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
56.7 | 368. | A | Stephenson and Malanowski, 1987 | Based on data from 353. to 458. K. See also Stull, 1947.; 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 |
---|---|---|---|---|---|
353. to 458. | 5.72759 | 2430.085 | -33.526 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
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
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.9 ± 0.1 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 824.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 793. | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.8 | PE | Mohmand, Hirabayashi, et al., 1981 | LLK |
10.08 | PE | Holmes, Terlouw, et al., 1979 | LLK |
9.9 | PE | Van Dam and Oskam, 1978 | LLK |
10.28 | PE | Van Dam and Oskam, 1978 | Vertical value; LLK |
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
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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 | Chemical Concepts |
NIST MS number | 162950 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Source | Dann, 1947 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 10568 |
Instrument | n.i.g. |
Melting point | 72 |
Boiling point | 184.7 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Clopatt, 1932
Clopatt, J.A.,
Eine neue Methode zur Bestimmung der Verbrennungswarme fluchtiger Stoffe,
Soc. Scient. Fenn. Commentat. Phys. Math., 1932, 6, 1-15. [all data]
Bruylants and Stassens, 1921
Bruylants, P.; Stassens, A.,
Contribution a letude des composes a noyau trimethylenique,
Bull. Cl. Sci. Acad. R. Belg., 1921, 7, 702-719. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Gladstone, 1959
Gladstone, T.P.,
Unpublished, 1959, Shaw-Shawinigan Chemicals Ltd., Sept. 1959. [all data]
Anonymous, 1955
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [all data]
Lynn, 1925
Lynn, G.,
, Thesis, 1925. [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]
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]
Mohmand, Hirabayashi, et al., 1981
Mohmand, S.; Hirabayashi, T.; Bock, H.,
Gasphasen-reaktionen, 22. Thermische erzeugung von C4H4O: Vinylketen und ethylidenketen,
Chem. Ber., 1981, 114, 1609. [all data]
Holmes, Terlouw, et al., 1979
Holmes, J.L.; Terlouw, J.K.; Vijfhuizen, P.C.; A'Campo, C.,
Metastable ion studies XII-Molecular and fragment ion structures for isomeric C4H6O2 acids,
Org. Mass Spectrom., 1979, 14, 204. [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]
Dann, 1947
Dann, O.,
Chem. Ber., 1947, 80, 427. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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