2-Butenoic acid, 1-methylethyl ester
- Formula: C7H12O2
- Molecular weight: 128.1690
- IUPAC Standard InChI: InChI=1S/C7H12O2/c1-4-5-7(8)9-6(2)3/h4-6H,1-3H3/b5-4+
- IUPAC Standard InChIKey: AABBHSMFGKYLKE-SNAWJCMRSA-N
- CAS Registry Number: 18060-77-0
- 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: Crotonic acid, isopropyl ester; Isopropyl crotonate; Isopropyl 2-butenoate; (E)-2-Butenoic acid isopropyl ester; CH3CH=CHC(O)OCH(CH3)2; Crotonic acid, isopropyl ester, trans
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -98.2 ± 0.7 | kcal/mol | Ccb | Schjanberg, 1936 | Heat of formation derived by Cox and Pilcher, 1970 |
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -109.2 ± 0.6 | kcal/mol | Ccb | Schjanberg, 1936 | Heat of formation derived by Cox and Pilcher, 1970 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -959.00 ± 0.60 | kcal/mol | Ccb | Schjanberg, 1936 | Reanalyzed by Cox and Pilcher, 1970, Original value = -958.4 kcal/mol; At 293 K; Corresponding ΔfHºliquid = -109.25 kcal/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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 11.0 ± 0.3 | kcal/mol | E | Schjanberg, 1936 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
| ΔvapH° | 11.0 | kcal/mol | N/A | Schjanberg, 1936 | DRB |
IR 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.
Data compiled by: Coblentz Society, Inc.
Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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| Owner | COBLENTZ SOCIETY Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | TENNESSEE EASTMAN COMPANY, RESEARCH LABORATORIES |
| Source reference | COBLENTZ NO. 787 |
| Date | 1960 |
| Name(s) | isopropyl (2E)-2-butenoate |
| Instrument | Not specified, most likely a prism, grating, or hybrid spectrometer. |
| Path length | SMEAR |
| Resolution | 4 |
| Sampling procedure | TRANSMISSION |
| Data processing | DIGITIZED BY NIST FROM HARD COPY |
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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Due to licensing restrictions, this spectrum cannot be downloaded.
| 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 | 150150 |
Gas Chromatography
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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
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | SE-30 | 150. | 864. | Ashes and Haken, 1975 | He, Celatom silanized (62-72 mesh); Column length: 3.7 m |
| Packed | OV-1 | 150. | 863. | Ashes and Haken, 1971 | |
| Packed | SE-30 | 150. | 863. | Germaine and Haken, 1969 | Celite 560; Column length: 3.7 m |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 863. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Schjanberg, 1936
Schjanberg, E.,
Die verbrennungswarmen und die refraktionsdaten einiger crotonsaureeste,
Z. Phys. Chem., 1936, 175, 289-342. [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]
Ashes and Haken, 1975
Ashes, J.R.; Haken, J.K.,
Gas chromatography of homologous esters. IX. Structure-retention increments of unsaturated esters,
J. Chromatogr., 1975, 111, 1, 171-187, https://doi.org/10.1016/S0021-9673(01)80159-X
. [all data]
Ashes and Haken, 1971
Ashes, J.R.; Haken, J.K.,
Gas chromatography of homologous esters. Part V. Retention of aliphatic esters on non-polar, donar and acceptor stationary phases,
J. Chromatogr., 1971, 60, 33-44, https://doi.org/10.1016/S0021-9673(00)95527-4
. [all data]
Germaine and Haken, 1969
Germaine, R.W.; Haken, J.K.,
Gas chromatography of homologous esters. Part 2. Unsaturated esters,
J. Chromatogr., 1969, 43, 43-47, https://doi.org/10.1016/S0021-9673(00)99163-5
. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Notes
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- Symbols used in this document:
ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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