Cyclopropanecarboxylic acid
- Formula: C4H6O2
- Molecular weight: 86.0892
- IUPAC Standard InChIKey: YMGUBTXCNDTFJI-UHFFFAOYSA-N
- CAS Registry Number: 1759-53-1
- 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: Carboxycyclopropane; Cyclopropionic acid; Cyclopropylcarboxylic acid; Cyclopropylmethanoic acid; Cyclpropanecarboxylic acid
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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 |
---|---|---|---|
22.65 | 298.16 | Tabacik V., 1978 | |
26.429 | 353.16 | ||
29.661 | 403.16 | ||
32.591 | 453.16 |
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
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 196.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 188.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.64 | PE | Holmes, Terlouw, et al., 1979 | LLK |
De-protonation reactions
C4H5O2- + =
By formula: C4H5O2- + H+ = C4H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 346.0 ± 2.2 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 339.0 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
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
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 900. | Peng, 2000 | 15. m/0.53 mm/1. μm, He; Program: 40C(3min) => 8C/min => 200(1min) => 5C/min => 300C(25min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1811. | Peng, 2000 | 15. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Tabacik V., 1978
Tabacik V.,
Vibrational spectra in cyclopropane series. III. Fundamental modes of cyclopropanecarboxylic acid monomer and of its -OD species,
Spectrochim. Acta, 1978, A34, 315-329. [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]
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]
Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P.,
Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria,
Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092
. [all data]
Peng, 2000
Peng, C.T.,
Prediction of retention indices. V. Influence of electronic effects and column polarity on retention index,
J. Chromatogr. A, 2000, 903, 1-2, 117-143, https://doi.org/10.1016/S0021-9673(00)00901-8
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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