2-Butenoic acid, methyl ester, (E)-
- Formula: C5H8O2
- Molecular weight: 100.1158
- IUPAC Standard InChIKey: MCVVUJPXSBQTRZ-ONEGZZNKSA-N
- CAS Registry Number: 623-43-8
- Chemical structure:
This structure is also available as a 2d Mol file - Species with the same structure:
- Stereoisomers:
- Other names: Crotonic acid, methyl ester, (E)-; trans-2-Butenoic acid methyl ester; Methyl trans-crotonate; Methyl trans-2-butenoate; (E)-2-Butenoic acid methyl ester; Methyl crotonate, (E)-; (E)-CH3CH=CHC(O)OCH3; (E)-Crotonic acid methyl ester; Methyl α-crotonate, trans-; Methyl E-crotonate; Methyl 2-butenoate, (E)-; Methyl (E)-2-butenoate; 2-Butenoic acid, methyl ester, (2E)-; Methyl E-propene-1-carboxylate; Methyl crotonate
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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 | -81.7 ± 0.5 | 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 | -91.5 ± 0.4 | kcal/mol | Ccb | Schjanberg, 1936 | Heat of formation derived by Cox and Pilcher, 1970 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -651.9 | kcal/mol | Ccb | Schjanberg, 1936 | At 293 K; Corresponding ΔfHºliquid = -91.6 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:
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 392.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 394.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.8 ± 0.3 | kcal/mol | E | Schjanberg, 1936 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
ΔvapH° | 9.80 | kcal/mol | N/A | Schjanberg, 1936 | DRB |
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 by: Edward P. Hunter and Sharon G. Lias
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 203.5 | kcal/mol | N/A | Hunter and Lias, 1998 | |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 196.1 | kcal/mol | N/A | Hunter and Lias, 1998 |
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 | Japan AIST/NIMC Database- Spectrum MS-NW- 668 |
NIST MS number | 229491 |
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, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BP-20 | 1100. | MacLeod and Pieris, 1983 | H2, 65. C @ 3. min, 12. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tend: 180. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 756. | Pino, Mesa, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min |
Capillary | CP Sil 5 CB | 726. | Pino, Almora, et al., 2003 | 60. m/0.32 mm/0.25 μm, He, 60. C @ 10. min, 3. K/min, 280. C @ 60. min |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1094. | Varming, Petersen, et al., 2004 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 10. min, 6. K/min, 240. C @ 25. min |
Capillary | AT-Wax | 1088. | Pino, Almora, et al., 2003 | 60. m/0.32 mm/0.25 μm, He, 65. C @ 10. min, 2. K/min, 250. C @ 60. min |
Capillary | Carbowax 20M | 1110. | Suárez and Duque, 1991 | 2. K/min; Column length: 25. m; Column diameter: 0.31 mm; Tstart: 50. C; Tend: 200. C |
Capillary | Carbowax 20M | 1115. | Suárez and Duque, 1991 | 2. K/min; Column length: 25. m; Column diameter: 0.31 mm; Tstart: 50. C; Tend: 200. C |
Packed | Carbowax 20M | 1102. | van den Dool and Kratz, 1963 | Celite 545, 4.6 K/min; Tstart: 75. C; Tend: 228. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | MDN-5 | 761. | van Loon, Linssen, et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 270. C @ 5. min |
Capillary | MDN-5 | 760. | van Loon, Linssen, et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 270. C @ 5. min |
Capillary | Ultra-1 | 753. | Iwaoka, Zhang, et al., 1993 | 50. m/0.31 mm/0.17 μm, He, 30. C @ 4. min, 2. K/min; Tend: 210. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 745. | Vinogradov, 2004 | Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1094. | Takeoka, Buttery, et al., 1991 | 60. m/0.32 mm/0.25 μm, He, 30. C @ 4. min, 2. K/min, 180. C @ 25. min |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1115. | Sampaio, Garruti, et al., 2011 | 30. m/0.25 mm/0.25 μm, Hydrogen; Program: 35 0C (9 min) 5 0C/min -> 80 0C 1 0C/min -> 100 0C 16 0C/min -> 210 0C (20 min) |
Capillary | Carbowax 20M | 1100. | Vinogradov, 2004 | Program: not specified |
Capillary | DB-Wax | 1108. | Peng, Yang, et al., 1991 | Program: not specified |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 1102. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes
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]
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]
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]
MacLeod and Pieris, 1983
MacLeod, A.J.; Pieris, N.M.,
Volatile components of papaya (Carica papaya L.) with particular reference to glucosinolate products,
J. Agric. Food Chem., 1983, 31, 5, 1005-1008, https://doi.org/10.1021/jf00119a021
. [all data]
Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R.,
Volatile components from mango (Mangifera indica L.) cultivars,
J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633
. [all data]
Pino, Almora, et al., 2003
Pino, J.; Almora, K.; Marbot, R.,
Volatile components of papaya (Carica papaya L., maradol variety) fruit,
Flavour Fragr. J., 2003, 18, 6, 492-496, https://doi.org/10.1002/ffj.1248
. [all data]
Varming, Petersen, et al., 2004
Varming, C.; Petersen, M.A.; Poll, L.,
Comparison of isolation methods for the determination of important aroma compounds in black currant (Ribes nigrum L.) juice, using nasal impact frequency profiling,
J. Agric. Food Chem., 2004, 52, 6, 1647-1652, https://doi.org/10.1021/jf035133t
. [all data]
Suárez and Duque, 1991
Suárez, M.; Duque, C.,
Volatile constituents of lulo (Salanum vestissimum D.) fruit,
J. Agric. Food Chem., 1991, 39, 8, 1498-1500, https://doi.org/10.1021/jf00008a026
. [all data]
van den Dool and Kratz, 1963
van den Dool, H.; Kratz, P. Dec.,
A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography,
J. Chromatogr., 1963, 11, 463-471, https://doi.org/10.1016/S0021-9673(01)80947-X
. [all data]
van Loon, Linssen, et al., 2005
van Loon, W.A.M.; Linssen, J.P.H.; Legger, A.; Posthumus, M.A.; Voragen, A.G.J.,
Identification and olfactometry of French fries flavour extracted at mouth conditions,
Food Chem., 2005, 90, 3, 417-425, https://doi.org/10.1016/j.foodchem.2004.05.005
. [all data]
Iwaoka, Zhang, et al., 1993
Iwaoka, W.T.; Zhang, X.; Hamilton, R.A.; Chia, C.L.; Tang, C.S.,
Identifying volatiles in soursop and comparing their changing profiles during ripening,
HortScience, 1993, 28, 8, 817-819. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Takeoka, Buttery, et al., 1991
Takeoka, G.R.; Buttery, R.G.; Teranishi, R.; Flath, R.A.; Güntert, M.,
Identification of additional pineapple volatiles,
J. Agric. Food Chem., 1991, 39, 10, 1848-1851, https://doi.org/10.1021/jf00010a032
. [all data]
Sampaio, Garruti, et al., 2011
Sampaio, K.S.; Garruti, D.S.; Franco, M.R.B.; Janzantti, N.S.; Da Silva, M.A.AP.,
Aroma volatiles recovered in the water phase of cashew apple (Anacardium occidentale L.) juice during concentration,
J. Sci. Food Agric., 2011, 91, 10, 1801-1809, https://doi.org/10.1002/jsfa.4385
. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References
- Symbols used in this document:
Tboil Boiling point 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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