Cyclopropanecarboxylic acid

Formula: C₄H₆O₂
Molecular weight: 86.0892
IUPAC Standard InChI: InChI=1S/C4H6O2/c5-4(6)3-1-2-3/h3H,1-2H2,(H,5,6)
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

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference
94.77	298.16	Tabacik V., 1978
110.58	353.16
124.10	403.16
136.36	453.16

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-2035.	kJ/mol	Ccb	Bruylants and Stassens, 1921	Corresponding Δ_fHº_liquid = -396. kJ/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_liquid	-2007.	kJ/mol	Ccb	Roth and Ostling, 1913	Corresponding Δ_fHº_liquid = -424.3 kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity	Value	Units	Method	Reference	Comment
T_boil	456.2	K	N/A	Weast and Grasselli, 1989	BS
T_boil	455. to 457.	K	N/A	Frinton Laboratories Inc., 1986	BS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
58.9 ± 0.3	340.	EB	Steele, Chirico, et al., 2002	Based on data from 357. to 473. K.; AC
55.7 ± 0.2	380.	EB	Steele, Chirico, et al., 2002	Based on data from 357. to 473. K.; AC
52.4 ± 0.2	420.	EB	Steele, Chirico, et al., 2002	Based on data from 357. to 473. K.; AC
48.8 ± 0.4	460.	EB	Steele, Chirico, et al., 2002	Based on data from 357. to 473. K.; AC

Reaction thermochemistry data

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Data compiled by: John E. Bartmess

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Individual Reactions

C₄H₅O₂^- + = Cyclopropanecarboxylic acid

By formula: C₄H₅O₂^- + H⁺ = C₄H₆O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1448. ± 9.2	kJ/mol	G+TS	Caldwell, Renneboog, et al., 1989	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1418. ± 8.4	kJ/mol	IMRE	Caldwell, Renneboog, et al., 1989	gas phase

Gas phase ion energetics data

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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)	821.4	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	790.4	kJ/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^- + = Cyclopropanecarboxylic acid

By formula: C₄H₅O₂^- + H⁺ = C₄H₆O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1448. ± 9.2	kJ/mol	G+TS	Caldwell, Renneboog, et al., 1989	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1418. ± 8.4	kJ/mol	IMRE	Caldwell, Renneboog, et al., 1989	gas phase; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

SOLUTION (2% CCl4 FOR 3800-1340, 2% CS2 FOR 1340-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

gas; HP-GC/MS/IRD

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

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

View large format table.

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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes

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]

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]

Roth and Ostling, 1913
Roth, W.A.; Ostling, G.J., Thermochemische Untersuchungen in der alicyclischen Reihe, Ber., 1913, 46, 309-327. [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]

Frinton Laboratories Inc., 1986
Frinton Laboratories Inc., Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Measurements of Vapor Pressure, Heat Capacity, and Density along the Saturation Line for Cyclopropane Carboxylic Acid, N , N -Diethylethanolamine, 2,3-Dihydrofuran, 5-Hexen-2-one, Perfluorobutanoic Acid, and 2-Phenylpropionaldehyde, J. Chem. Eng. Data, 2002, 47, 4, 715-724, https://doi.org/10.1021/je010087j . [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]

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]

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

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
T_boil	Boiling point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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