2-Butenoic acid, (E)-
- Formula: C4H6O2
- Molecular weight: 86.0892
- IUPAC Standard InChI: InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+
- 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
View 3d structure (requires JavaScript / HTML 5) - 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, 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: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 9.94 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. |
| 13.4 | 100. | ||
| 16.8 | 150. | ||
| 20.0 | 200. | ||
| 24.40 | 273.15 | ||
| 25.88 | 298.15 | ||
| 26.00 | 300. | ||
| 31.67 | 400. | ||
| 36.52 | 500. | ||
| 40.49 | 600. | ||
| 43.76 | 700. | ||
| 46.51 | 800. | ||
| 48.85 | 900. | ||
| 50.86 | 1000. | ||
| 52.58 | 1100. | ||
| 54.06 | 1200. | ||
| 55.35 | 1300. | ||
| 56.45 | 1400. | ||
| 57.43 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°liquid | -498.3 | kcal/mol | Ccb | Clopatt, 1932 | Corresponding ΔfHºliquid = -82.8 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -478.0 | kcal/mol | Ccb | Bruylants and Stassens, 1921 | Corresponding ΔfHºliquid = -103.1 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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
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) | 196.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 190. | kcal/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 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, 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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy ΔcH°liquid Enthalpy of combustion of liquid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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